The Murder of Carol Stuart | Morbid | Podcast | Forensic Files

Hey weirdos, I'm Alina. I'm Ash. And this is Morbid. Hey, what's up? Hello. I think there is lawnmowers happening
outside and there's not we can do. I think you should run out there, run in front of them and say, "Hey,
Yeah. stop it." I can pull a The Happening and just lay in front of it. I That's not what I said at all. I told
you to tell them to stop. You're like choking the happening. No, don't happening.
Please don't happening. I'm not doing this show alone, so No, I will not happening.
Hey, hey, hey, she's not happening. It's true. She's not. She's tired. She's not happening.
No, this is our last recording before we get to take a little breaky. Yeah. You won't know that we're taking
know we're taking a breaky. Because we breaky it ourselves. To to get all these recordings in.
Yeah. You got to You got to bulk record to get a breaky. Yep. So In these streets.
In these streets. So, we don't know when this comes out, but there's really nothing pertinent that will affect that.
Yeah, I think it comes out like mid-May, so can pre-order the paperback version of
The Butcher Game. There you go. Looking for that paperback out there? I see you. I see you. You've been
waiting for that paperback. The paperback. is coming up. The paperback. The paperback. She's bringing paperback.
Oh, yeah. I like how you had to go "Yeah." It's my favorite part of the song. Um
It's beach season almost and vacation season and you need a paperback Yeah, that's in your beach bag.
It's a beach read. For sure. What kind of beach read? Yeah. I like it. So, go get it. You can get it at the
butchergame.com. It'll lead you to the places you can get it. Let's go. The Barnes & Nobles,
the all the places. Freakin freakin party. Freakin party with your paperback. Freakin party kid. Well, actually that
kind of transitions into what we're going to be talking about today. We got a Boston hometown case.
Oh my god, it's Boston. Yes, this is not one to be proud of, I'm sure. I was actually just going to say this is
a very devastating case. It's awful, but it's probably a case that I think if you're from Boston or
like anywhere around there, you're probably familiar with. Okay. Or if you're a fan of Law & Order, I
think they I remember seeing an episode that was very very similar to this. Oh, okay. So, today we're going to be
talking about the murder of Carol Stuart who seemed like a really [ __ ] cool person.
Oh, no. And it bumps me out. So, let's start at the beginning now. Carol Ann DiMaiti was
born March 26, 1959 in Medford. Medford kid. Medford Massachusetts. She was the second of two children born to Giusto
and Evelyn DiMaiti. Hmm. She grew up in a multi-family home, which is, you know, all homes around
here pretty much. Yeah. Her aunt Rosemary actually lived on the second floor of the house and there was
a lot of extended family like in their neighborhood, around their neighborhood. So, she and her brother always had a
really warm, loving support network all around. that. Yeah. So, at the time Medford was a
heavily Italian working class suburb of Boston, which meant that religion and the church were pretty central to the
lives of a lot of residents at the time. Carol went to Saint James school, which
was a Catholic school at that time run by nuns. She was a really really good student. She was well liked by her her
teachers, her classmates, friends of course. Pretty much everybody agreed that she could be whatever she wanted to
be when she was done with school. Damn. She was at the very top of her class and
all the classes that she was taking were AP or honors. Damn. insane. Yeah. don't know how people do
that. Not easy. No. And on top of all that, she also would uh volunteer and she worked in the
administrative office before school every morning. Wow. So, she woke up early and went to school
before she even had to. Oh, so she's really doing the damn thing. The school's headmaster, Sal Tedaro,
said, "She'd come into the office in the morning and it was like a ray of light coming in."
Aw. I know. But according to author Joe Sharkey, who wrote the book Deadly Greed about this
case, what teenage Carol wanted most of all was to be, quote, "married to a good
husband living in the suburbs with a couple terrific kids happily ever after." Aw.
Which is really cute and so relatable. Yeah. This goal, I'm sure for a lot of reasons, is what people are remembered
most about Carol. Her childhood friend, Robert, said, "Overall, her purpose in life was to
raise a good family. She got along with jocks, burnouts, wimps, geeks, headmasters, everyone. She was a very
pleasant person, painless to speak to, able to bridge the gap and and circle in all different groups."
Aw. She sounds really cool. Sounds like an all-around awesome person ever around.
Yeah, just like didn't give a [ __ ] who you were, just wanted to shoot like wanted to chat with you.
Like, let's go. And would would help you out. Now, when Carol was 15, her father found
her a part-time job at Driftwood, a restau- a restaurant on the main street of Revere Beach.
Revere, Ken. Revere's just a little ways away from Medford. Giusto Gemmati also worked at the
restaurant as a part-time bartender at night. So, it was a pretty good opportunity for his daughter to get some
work experience while he could also keep an eye on her. Ah, I see. It was pretty perfect.
Yeah, it really is. And a few years later, when Carol turned 18 and now she could serve drinks, she
moved up to work as a server. She was really great cuz again, she's a people person. People loved her.
And her coworkers loved her as well. Coworker Christine Baratta said, "When I met Carol, I met a big sister. She
taught me how to drive, she taught me how to wear makeup, taught me about clothes and hair. In a way, she really
helped me grow up." Aw. I know. That's really sweet. By the time she graduated high school in
1978, Carol had saved nearly $10,000 Damn. job. Holy [ __ ] And she planned to put that towards
school. She'd already been accepted to Boston University. And by the way, that would be a little more than $49,000.
going to say, and by today's standards, that's even more. $49,000 by today's standards.
Wow. Yeah. That's incredible. It's insane. At first, Evelyn and Justo questioned if college was really the
best choice for their daughter. But Carol was able to be, you know, successful and kind of
like, "Listen. I can make it happen." Yeah, she very much wanted to. She argued that BU was a Jesuit school, so
she could still be involved in the religious activities that they wanted her to, you know, be involved in.
Yeah. And to help ease their minds even more, she agreed that she would live at home
for the first 3 years and commute into the city for classes, even though she really wanted to live on campus and kind
of experience that freedom. Yeah. She just knew it was unlikely that she was going to win that battle.
Makes sense. So, when she first started BU, Carol had hoped to become a teacher, since she
always loved being around children. But by sophomore year, her sophomore year in
college, there were widespread layoffs and pretty poor funding for education in this area. So, that made the prospect of
becoming a teacher a bit less attractive. It wasn't going to, you know, really make her a lot of money or
anything like that. That makes sense. So, Carol changed her mind and she decided
to pursue a law degree instead. teaching. Yeah. But her objective was similar. Whatever
her career was going to be, she wanted it to help people. Aw. Make a difference in their lives.
that. Yeah. So, in 1978, she started seeing her first serious boyfriend, Chuck Stewart, one of the cooks from
Driftwood. Okay. A um a restaurant romance. We we love to see it. Sometimes. When they met in the summer of 1978, she
was still seeing her high school boyfriend, uh but she and she, you know, she wasn't really on the lookout for
somebody new, but as soon as she met Chuck, she was immediately interested. He was also a local. He was born and
raised in Revere, just a few miles outside of Boston. And, uh, also like Carol, he came from a pretty decent
Catholic home surrounded by adoring, doting family members, you know. You know, all sweet Bostonians, their
families run deep. It's true. I've heard it we really do. According to those who knew him best, Chuck was,
quote, ruggedly handsome, athletic, but not the kind of student that Carol became.
Oof. Yeah. When they started dating, Chuck told Carol that he was attending Brown
University on a football scholarship, but that he had to drop out after being sidelined with an injury.
Hmm. Um, like a lot of claims that Chuck would make over the years, this was a lie.
Oh. Yeah, one of many that he told in order to make himself seem more impressive
than he really was. Oh, no. In reality, he had never been a good student, uh, definitely not a good
enough student to go to Brown University. And even if he had been accepted to Brown, they didn't offer
football scholarships. Oh, no, Chuck. Yeah, so he was there was lots of layers that didn't work out with that lie.
You got caught. Yeah. The truth was he attended the local VoTech school and had gone to
Salem State University for one semester before dropping out within that first semester.
And it's like man, I don't I don't know a lot about this case right now, but I'm like that's it's
fine that's fine. Yeah. Just be honest, man. It's okay. Like the people who like you are going to like
you for who you are. And college is college. Not everybody gets accepted to college or
People shouldn't be like liking you based on where you went to school. And Salem State is also a great school
in a [ __ ] fantastic location, if we do say so ourselves. But he he wanted to be more than what he
saw that as. That makes sense. So, Carol and Chuck, like I said, they shared a lot of things in common, but
there were also some stark differences in the ways that they'd grown up. Both were from solidly middle-class
families, but Chuck's family had struggled financially at times, and he was always a little ashamed of that.
Mhm. By the time he reached high school, they were living in a modest two-story home
two blocks from the school that he and his brothers went to, but they had previously lived in public housing, and
that was something Chuck was really embarrassed about. Okay. And with four boys living in the family,
the house was kind of always in a state of disarray cuz boys are pretty messy typically. One of Chuck's friends said
that the way Chuck described it was too many kids, too much yelling and fighting, the place was always a
[ __ ] Oh. So, he just he didn't like the way he grew up. Yeah. Which, you know, that's
It is what it is. their own. Yeah. I'm sure his parents did their best. Yeah. According to some who knew him, Chuck's
attitude towards his upbringing and shame surrounding his family really made a lot of sense, and it just pointed to
his arrogant and usually snobby personality. Ah. One former friend said, "He always let
you know that he thought he was better than you." Oof. Which, like, that's not a great friend
to have. Because he was the oldest and the firstborn, he was, quote, "lavished with
attention" before it was gradually withdrawn as the Stewart house became crowded with children.
Oh, that and that's tough when you're when you're a kid. That's tough. As an adult, you get the [ __ ] over it.
That's the thing. But as a kid, it's tough when you have all the attention, I'm sure. I was the
youngest, so I don't relate to this at all. Like, I was the one sucking up all the attention, so sorry, siblings.
I mean, but then I came around when you were 10. That's true. So. Uh but it it that can I'm sure that's
tough when you get all the attention as a kid and then it's kind of has to be divvied up. Yeah, I'm sure. You know?
I wouldn't know. You're like me. I don't know. I'm like an only child, but also not, so
I'm like a I'm in a weird place in my family. Yeah, you do have a strange a strange
place. my my only child, but then with you guys, you were all like siblings to me
cuz I like grew up in that household. like the youngest of that. I feel like the youngest of that, the
only of my mom, and then the oldest on my dad's side. So I kind of have like all the boxes ticked.
You really do. It's weird. So yeah, I don't know a lot about that. But as far as someone concerned, the
lack of his parents' constant adoration and attention left Chuck with a sense of
frustration and a kind of like a a mild bitterness that he would carry with him the rest of his life.
Yeah, you got to drop that. Which is crazy. You got to you got to drop that sometimes.
Yeah. And there was also the matter of where he grew up. Unlike Medford, which is easily accessible from Boston and,
you know, points north, Revere was a little bit isolated for a lot of its history.
Mhm. In the summer, the railroad brought tons and tons of tourists to the beach, to
the boardwalk area, but otherwise the city was difficult to get to and mostly operated independently from the cities
from surrounding cities and towns. Okay. Yeah. By the 1970s, the beach also wasn't
really a popular place for tourists to go, and the area was just kind of in a general decline that got worse
throughout the years. For somebody like Chuck who always wanted to be seen as this very successful guy, his hometown
became a source of shame, which is stupid. Yeah, it's like, come on. Plenty of people come from plenty of
places that aren't fantastic. And it's like, you didn't you didn't build the city. And also like, it's
okay. Like no one's blaming you for it. Revere's fine. Yeah, it's fine. But as soon as he was able to, he got
himself out of Revere cuz he thought it was awful. Only to return for short visits with friends and family.
Now, when they got together, to a lot of people around them, Chuck and Carol's relationship seemed a matter of
convenience more than anything else. Mhm. Carol's high school boyfriend had gone
off to college and long distance wasn't working out for them. But Chuck, on the other hand, was right there at the
restaurant. He seemed to he seemed very determined to catch Carol's eye and do whatever he could to get her to go out
with him. Huh. Christine Baratta said, "He wanted her. That was it. He went after her."
Woah. Yeah, which sometimes that can be a really cute start to a love story. Yeah.
And other times it's not here. a red flag. Yeah. Carol's decision to date Chuck was
actually a major point of contention between her and her dad. Really? Yeah, her dad obviously believed that
his daughter deserved the best of everything. Of course. And as far as he could tell, Chuck
Stewart wasn't really the best. I mean, that that's tough. That is tough. That's tough as as a parent, tough as
the kid. Yeah, it's tough for everybody. It's It's definitely tough for Chuck. That's
tough. see both sides of that. Yeah. But regardless of how her father and others felt about Chuck, Carol was
determined to make her own decisions. And she decided she wanted to give this relationship with Chuck a chance.
Which is her right. Chuck a chance. Chuck a chance. You know, give Chuck a chance.
To her friends and her coworkers, especially the female ones, Carol's decision made sense.
Chuck wasn't really brimming with personality and charm, but he was good-looking. He was well-mannered, and
most importantly, in the beginning, he adored Carol. And it seemed that the more Carol's father protested and
complained, the more attentive and adoring Chuck became. Oh. Almost like he was trying to win that
top spot in Carol's life. That stresses me out in every way that you can conceivably stress me out.
Ridiculous. It just won't happen. We won't allow it. Oof. But that's the thing, sometimes as a
parent, I think you can go too hard. Well, that's and you And you you send them right in the other
direction. do you know that line? And How do you know what line is the line that tips it that way?
Well, and it can be that's so hard. I think the scary thing, too, is that it can be one line for your kid.
It Well, one line for your kid, but another line for the partner. Yeah, you're absolutely right.
like you might push them in a different direction, too. Oh, man. Which is scary.
I hate it. Yeah. Well, one friend said Carol liked that he was different from other guys. That
uh called all the time. He'd send her little gifts, little tokens. He was very good at expressing love. With Chuck, it
was always flowers here, flowers there. Okay. Which is nice. Yeah, I mean, that's nice.
can also be love bombing. It's really hard to be a woman because You don't know.
You just never know. Yeah, you really don't. Yeah. As Carol worked her way through
undergrad, her relationship with Chuck intensified and got a lot more serious than really anybody had expected. By the
time Carol graduated uh from BU in June of 1981, she and Chuck were talking about getting married. But Carol
insisted that she wanted to wait until she was done with law school, which she was going to be starting at Suffolk in
the fall. Good for her. I know. She did the damn thing. Chuck was disappointed with Carol's
decision to wait. He really wanted to get married when she finished at BU, but ultimately he was like, I I can't force
you to marry me, so we'll follow through with that plan. Yeah. In the meantime, he decided finally to
start taking his own future more seriously, and he started looking for a better job.
Until that point, he actually had dreams of opening his own restaurant, but with
Carol starting law school, he had to accept that that dream of restaurant ownership was
a bit unrealistic in the short term. Restaurants, from what I've heard, are it's a tough business. Incredibly tough
to like when you're like buying one and owning it. Yeah. Yeah, I can't imagine that.
It can go really well, but the statistics are that it doesn't. And when it goes not well, even if it's
just going kind of well, you are bleeding money. And you have to pour a lot into it. Like
that's not just like, oh, I'm going to have a restaurant and hire people to work there. It's like it becomes your
life. absolutely does. So, he realized for probably a lot of those reasons that it just wasn't the
time to to go down that path. Yeah. So, instead he made his way to downtown Boston where he found work as a manager
in training at Edward F. Kakas & Sons, a furrier on Newbury Street in Back Bay, very flouncy area.
excuse you. I know. A furrier. A furrier. Which I don't love. Don't wear fur. No.
When he applied for the job, Chuck had no management experience and no experience with high-end clothing,
either. But the owner just took a liking to him and soon Chuck found himself on the path to a pretty promising career.
I'm always amazed at the the amount of stories we hear that have that And they never had experience
Like but but it was just something about them that the the person like the boss was like, I just hired him. I just liked
him. liked him. You're like, what the [ __ ] is that? Like what is that about someone?
I think in cases like this I think like where it's somebody who has a sinister vibe like hidden within
them, they study other people. Yeah, I could see that. like know how to charm people.
Yeah, you're right. I mean? absolutely part of it. And I think in good people it's just a
cool quality that they have. Yeah, and bad people it's a scary one. Yeah. Yeah. Well, true to Carol's plan, she and
Chuck did indeed get married on October 13th, 1985, the year of your birth, at a large ceremony at St. James Church,
the same church where her parents got married, so that was special. Yeah. By the time they married, Chuck had
moved up at the at Kakas and Sons and was making around $50,000 a year, which would be about
$148,000 today. So, For you it would be damn good. Yeah. And they were able to move out of
Medford and buy a house in a more upscale area called Reading. It's about 25 miles from Boston. It's a really nice
area. From the outside, Carol and Chuck's marriage seemed like an ideal match. The more like the older they got
and the more time they spent together. He was a leading salesman and manager. She was on track to becoming a
successful tax lawyer. They had two labs. They had a pool. They were really going for it.
Yeah, like they were very all-American, you know, like that that couple that everybody aspires to be. The picture of
the suburban success. But behind the scenes, Carol was already having doubts. She was frustrated that despite her
years of training and all the work she'd put into her getting her education, she
was entering the workforce making a lot less than her husband who had no training and virtually no education to
speak of. That can be frustrating. She's like I worked really hard. And I'm not making a lot less money.
And she's probably in a lot of debt, too. And he just was charming and got this job. That's that is frustrating.
Yeah, and obviously you want to be happy for your partner, but there were other things at play here.
Joe Sharkey wrote, "It was the first time anyone had heard Carol disparage Chuck's education." And to make matters
worse, Chuck always had a way of working his salary into conversations when they
went out with friends. Yeah, that's gross. We don't love that. We don't do that. That's not appropriate
dinner table talk. So Carol might not have seen it or maybe just didn't want to, but there were also
other things about Chuck's personality that her friends and family were starting to find concerning.
Her friend Robert said, "There was just something not quite right about Chuck. It wasn't natural. It's hard to put your
finger on it. He seemed smooth enough, a little much with the blown back hair, but nicely tied together anyway, but not
natural, you know?" I'm kind of obsessed with that. A little much with the blown back hair.
I like that He's like, "I'm just telling you something wasn't right." So so [ __ ] that guy's hair.
I guess he was all right. Look kind of stupid with the [ __ ] hair, but like What's going on?
Yeah. But others found his Chuck seemingly like insatiable materialism to be a little off-putting.
I can understand that. that. At the time people felt it should have been Carol who was, you know,
interested in shopping and her appearance. And they thought it was weird that it was Chuck who cared a lot
more about those things. And even weirder, stranger, that he made no secret of dismissing Carol's wants in
favor for his own. Ooh. Yeah. It wasn't just that he seemed wildly materialistic. To some it just
seemed like another way for Chuck to be the dominant one in their relationship and
Yeah. kind of like hold his success over Carol's head. That makes sense. Yeah. The more Carol's friends got to
know Chuck, the more they found that something in their relationship was just disturbing.
Mhm. But like Carol's friend Robert, they couldn't really put their finger on exactly what it was. Cuz it wasn't that
Chuck was abusive in any recognizable way. Carol doted on her husband endlessly though and he didn't seem to
reciprocate. Which like that could be tough to see. Yeah. And then there was the matter of him
constantly keeping tabs on her. He wasn't what any of her friends would say was overly jealous, but he quote always
wanted to know exactly where his wife was. Mhm. Which like Yeah. You can see that as nefarious. I think
it was probably in the way he went about it. Cuz it could also just be protective.
Absolutely can and it's I think it it can easily look nefarious in with the power of hindsight.
Yeah. I think that's that's where it gets a little easier to look at things and it's
like, "Huh. That seemingly innocuous thing was a little weird." Yeah, looking back. And also in tandem
with other things. That's the thing. By the late '80s when Carol started commuting from Reading to her job in the
city, Chuck bought her a cell phone so that she could keep in touch with him during the commute. Another one of
Carol's friends, Mark Brady, remembered, "She always had this damn car phone and
as soon as we got in the car she'd pick it up and report in." Mhm. Which like that if I if I was with a
friend who constantly was like, oh I have to let my husband know where I am. I have to call Chuck and and report
where I am. are you okay? I'd be like, is everything cool? Yeah. And that it sounds like her friends were
like, is that is everything okay? just like, is something going on here? Yeah, so by 1987, Chuck also insisted
that Carol find a new job closer to home. You don't get to tell me where I work.
I'm sorry, excuse me? Yeah, no. No. I don't like that. No. That's a discussion that you can have as a couple of like,
would this make more sense Nope. for us as a couple? As a husband, you don't get to tell your
wife where she works. a no for me. No, as a partner, you don't. Mhm. So, she did though. She took a job as a
tax lawyer for I think it's Kaner's Publishing in Newton. Okay. Um the house turned out to be an
improvement over her last job, but to Chuck's disappointment, not long after she started there, they insisted that
all of their tax staff needed additional education, so they enrolled Carol in night classes at the U.
Oh. Yeah, he didn't love that. I'm sure he didn't. Carol though had always loved education,
and she was really loving these new classes, which in turn kind of seemed to inspire this like new self-confidence in
her that her friends and family hadn't seen before. She was doing well in her classes, but friends also were noticing
that she was standing up to Chuck more often, even over like trivial matters. Interesting.
On one occasion when he and his friends came home drunk from a hockey game, she demanded that his friends leave
immediately. She was like, I'm not having this in my house, get out of here. Yeah.
Which was very unlike her, and it was it was super late at night, like Yeah, you you stand up.
Yeah. Chuck protested, but Carol eventually won the argument and the other men left.
Good. A few days later, she confessed to a friend that she was being unreasonable,
but she was also proud of herself for standing up to him. Yeah, sometimes you you assert yourself
in a way that you're like, ah probably wasn't the situation, but I did yeah, I think especially when you're not
used to asserting yourself and you finally find the nerve to, it might not it might not be the right time, but you
did it. Mhm. So, as the '80s came to a close, Chuck and Carol's relationship had grown more
and more tense. And at the same time, Chuck seemed to be spending a lot more money, like on things like clothing and
jewelry than he ever had. Mhm. While Carol bought all her clothes at, you know, mid-tier stores like Filene's
Basement, TBT. Ooh, Filene's Basement, I remember that. And uh she shopped at Marshalls. Chuck
bought all of his custom suits from Brooks Brothers, Brooks Brothers, and other similarly expensive stores.
Damn. Brooks Brothers is like on Newbury Street. It's like that caliber. a for sure.
So, Carol didn't really complain about it, but there were times when she became exasperated while venting to her friends
about how much he paid for things. And she was like, "I don't understand why he needs $1,200 sweaters."
I mean, valid. Most times though, she just shrugged it off and said something about how he knew
clothes better than she did. What she didn't know though was that his spending habits were racking up very
serious credit card debt. Oh, no. And delinquent payments were also beginning to pile up.
Uh It turned out that Chuck's spending and mounting debt weren't the only secret he
was keeping from his wife either. I'm sure we all saw this one coming. Yep. In the summer of 1989, he took a liking
to the new summer employee at Kakkis. Oh, no. A college student No. named Debbie Allen.
Like Carol, Debbie had been a dedicated student who was doing really well in school and had taken the job at the
furrier for the summer with plans to go back to Brown University to finish her senior year in the fall.
She had a boyfriend at the time and didn't express interest in Chuck, but he seemed determined to, quote-unquote
obtain her. Oh, stop it. Just like he had all those other things in life that he thought were out of his
reach. I hate it. He is like he's compulsive. Yeah. With like He acquires things.
And people. And he looks at people as things that he acquires. Yeah, and he just can't help himself.
Yeah. Now, shittily enough, his interest in Debbie emerged not long after Carol started talking to her husband more
seriously about starting a family together. So, here's Carol being like, I you know, like let's let's
get the spending under control. Let's like come home a little more. Let's not go out with our drunk friends all the
time. And let's Yeah. have a baby. Like we're at the right age. like behavior. Yeah, they've been married a few years.
Yeah. They're doing well in their careers. And she wants to have a family. And he's
like, "Yeah, I think I want to have an affair with the new summer employee at at work, though."
Cool. That's good. Yeah, that's great. Yeah. And he knew that she wanted kids. Carol had never been shy about her
desire for a family. Remember in the at the top of this episode, it was like the
one thing anyone could tell you about her. But Chuck, whenever he talked about having kids with his friends, he didn't
try to even hide his disdain for the idea. He did not want kids. Oh my god. That spring, he apparently told a
friend, "I knew it was coming just as soon as things started falling into place."
I'm sorry, what? Like what? I'm sorry, what, sir? Yeah. And the more and more she quote-unquote
pushed to have kids, the more Chuck complained about her secretly, suggesting that not only did he not want
to have kids, but he also wasn't even really interested in being married to Carol anymore.
Oh, thing go away. Then divorce. Yeah, thing go away. Given all his complaints about Carol and
his not wanting to have children, most of his friends and family were uh a little more than surprised when in
early 1989, Carol announced that she was pregnant. Which also it's like, my guy,
if you don't want kids you got to be up front about that. You got to be up front and it's like you
know how kids are made. Mhm. So it's like why like you got to you got to talk about it, you got to
take a precaution. Yeah. You guys are in a position where you can. Yep. So like what are you doing?
What are you doing? So approaching his 30th birthday, Chuck had these big dreams for himself. He'd been moving up
at the store and now he was even planning to uh and saving to open his own restaurant. He is going down that
road. Okay. His vision for the future was fun, excitement, excess. Carol on the other
hand had her own dreams of settling down in the suburbs, having a family, living
a quiet life. Yeah. They are on complete opposite ends of the spectrum. When she became pregnant in the winter
of 1989, it seemed like that's where they were headed, that quiet suburban life.
At first, Chuck had even tried to convince his wife to get an abortion arguing that he was on the cusp of
reaching his goals and a baby just didn't fit into those plans. But Carol was like absolutely not.
Because again You should have discussed this beforehand. You should have discussed this before
you even got married. Yeah. Like absolutely. Meaning you should have been up front
with her saying I don't think I want kids. That's not what I want. I don't I don't think that's part of my
plan. Right. That needs to be part of the discussion. But then he wouldn't have been able to
obtain her. So I'm sure who knows what those discussions were, but I have an inkling that he was probably like, "Oh
yeah, totally. I want kids. You want kids? I want to least just like fluffing around it,
yeah. Yeah. Eventually he gave up trying to convince Carol and as far as anybody could tell
just became compliant if not an exactly supportive husband and father-to-be. On the evening of October 23rd, 1989,
Carol picked uh Chuck up on Newbury Street and they drove to Brigham and Women's Hospital to go to a childbirth
in class. Oh. But as she pulled onto Mass Ave, they hit a really serious traffic jam that
would have had them tied up for a while. The traffic put uh put Chuck in a really
bad mood, but they did make it on time and they went to the class as planned. The class ended a few minutes early
actually and Carol who had a lot of questions was eager to talk to the instructor, but Chuck was like no, we
have to go. We have to go. Let's get out of here. Wouldn't let her ask any of her
questions. on. Later when they were interviewed by police, one of the other attendees at
the class said Chuck was quote really out of it and couldn't wait to get out of the class.
That's sad. Now, the way home from the hospital should have been considerably easier
because they didn't have to go back through the city, but Chuck had a habit of going home the same way that they
came in. So, they headed back into the city. Which like doesn't make a lot of sense.
No. When you're leaving and you don't have to go through the city again, you aren't
going to choose to. No. But this route took them through Roxbury which at the time was a pretty dangerous
neighborhood. Yeah. Carol was always nervous driving through this particular area. So, Chuck's
decision to do so would have probably been cause for alarm, but she trusted him.
Yeah, of course. He was in the driver's seat so she wasn't going to argue. Yeah.
And he'd already been in a bad mood so she was probably just like okay, like sounds good.
At a certain point in their trip, Chuck brought the car to a stop at a red light
on Huntington Ave where he claimed they were approached by a young black man who
forced his way into the backseat and pressed a gun to Chuck's head. You know this case.
I very much know this case. It took me a minute. I absolutely know this case now.
Yep. Yep. Oh, [ __ ] I hate this guy. Yeah. Later Chuck would say the man forced him
to drive the car to the Mission Hill area of Roxbury and told him to stop in what Chuck described as a quote unquote
abandoned area across from one of the multi-story public housing projects. Things got more intense Chuck said when
the man saw the cell phone in the console between the driver and the passenger seat and thought Chuck was
possibly a police officer. He said the man told him, I think you're 5-0. Chuck protested, but he said the man
only grew more suspicious because um Chuck said he didn't have a wallet when the man asked. And it was at that point
that he said the man shot Carol point-blank in the head and shot Chuck once in the stomach and then left.
Mhm. The call came into Massachusetts State Police dispatch a little before 9:00
p.m. with Chuck yelling into the phone, "My wife's been shot. I've been shot." He told the dispatcher that they'd been
driving home from the hospital when they were carjacked, but that the carjacker shot them and fled, and now he had no
idea where they were. And then he asked the dispatcher, who was frantically trying to figure out
their location, "Should I drive or should I should I try to drive or should I stay right here?"
It's like, why would you try to drive? No, you've been shot. Like, what are you talking And also, I
love that he's like, "Yeah, I don't know where they are, but I do know they were
black." Yeah. That's for sure. Yep, definitely. Yep. The dispatcher insisted that Chuck uh
definitely not drive, uh but he started the car anyway and drove a few feet before bringing it to a stop again and
saying, "Oh man, I'm going to pass out. It hurts and my wife has stopped gurgling. She stopped breathing. I'm
blacking out." Oh my god. Without a more specific location, the dispatcher just ordered a flood of
police cruisers to the Mission Hill neighborhood to start looking for Chuck and Carol. And in the meantime, the
dispatcher Gary McLaughlin did his best to keep Chuck alert and responsive while
also listening on the call for the sounds of sirens so that he could keep guiding the police towards Stewart's car
towards the Stewart's car. Later, McLaughlin said, "It was a unique call. You don't get many of these in
your career. There was a definite urgency in the man's voice. We didn't have a lot of time to find out where he
was." So, it took them 10 minutes to find the car on Saint Alphonsus Street parked
underneath a burnt-out streetlight with the driver's side window rolled down. Huh.
Which is like, why would you you like why did you move the car to begin with and why did you move it under a dark
street lamp? Like, what are you doing? But to the paramedics, the scene did look a lot like domestic violence scenes
that they'd encountered a lot of times in the past. And as they moved Carol removed Carol from the passenger seat,
that was when they realized she was pregnant. Oh. By the time she was loaded into the
ambulance, she had lost a lot of blood and suffered a tremendous injury to her head. And it seemed very unlikely to
anybody that she would make it. That's so sad. It is really sad. Chuck, incredibly, had
fared actually far better in the attack. Crazy. But he still suffered a traumatic
gunshot injury to his stomach and was bleeding quite heavily. So Carol was sent back to Brigham and
Women's where doctors did manage to deliver her baby prematurely. Wow. Which is incredible.
Brigham and Women's? Incredible. the most incredible hospitals. But unfortunately, they were unable to
save Carol and she died a little after midnight. Oh, that's so sad. Yeah. Chuck, meanwhile, was taken to Boston
City Hospital where he was listed as being in critical condition. Coincidentally, the entire remarkable
rescue was caught on tape by the crew of Rescue 911. Holy [ __ ] Bring me right back.
Yeah. I can literally oh I I can smell me sitting in a chair I can smell the chair
I can I'm there. I [ __ ] loved Rescue 911. Well, they were riding along with Boston
paramedics that night and they caught this entire thing. Holy [ __ ] Yeah. I didn't know that part of it.
Isn't that crazy? Wow. So as soon as he was stable, Chuck Stuart gave a statement to the police
where he described the shooter as a young black man with a raspy voice dressed in a tracksuit.
He's like, let me give you so much detail. It was just also in short a pretty [ __ ] racist stereotype of the kind of
person 100%. who at least in the minds of a lot of white suburbanites at the time would
commit this kind of crime. Yeah. Like, that's the most racist description ever. Yeah, he might as well have just been
like, "Hey, I'm a huge racist." Yeah. But here's the description. Thumbs up. Yeah.
That night, Boston Mayor Ray Flynn issued a statement from the Roxbury Police Precinct regarding the Stuart
shooting saying, "I demand the Boston Police Department continue to be extremely aggressive in cracking down on
people who are using guns and killing innocent people. It's intolerable. We will use every lawful tool to support
our police officers in cracking down on gun-wielding criminals." Especially this white guy who just did it and is
now lying about it. Carol's murder had come during a time when Boston was experiencing a
particularly troubling wave of gun violence. I think now it's just the norm, but back then it was like, "Holy
[ __ ] this is happening all the time." Just a few days earlier, 12-year-old Darlene Moore had been shot and killed
in what was described as a gang-related shooting. And that same night, 29-year-old James Moody was gunned down
in Dorchester. City Councilor Bruce Bowling told a reporter, "People felt as long as all
this violence was in the greater Roxbury neighborhood, it's not going to affect us. Now we see it's not confined to a
single race or ethnicity." It was definitely true that violent crimes were touching the lives of both
white and black residents, but when it came to the response from law enforcement in this case, in the Stuart
case, it seemed to a lot of people that the Stuart case was given much more priority than black victims of crime.
In Roxbury, the mother of 15-year-old LaRusha Harris criticized Boston police for their inability to make progress on
the attempted murder of her daughter while they wasted no time flooding the streets to find Carol Stuart's killer.
course. Neighbor Jacqueline Sims told a reporter, "That's a feeling a lot of black people have. I do, too. It seems
like the since the Stuart thing happened, everybody's coming down on the black area."
And see, look what he caused. Look what he did. Obviously, details and intricacies of
murder cases are always very complicated, but it does seem like this murder, the Stuart murder, got far more
attention from the press and the police than other incidents of violent crime that occurred in the exact same area.
Yeah. At the the exact same time. By their own admission, investigators had no leads and no witnesses, but the
morning after the shooting, dozens of Boston police officers like were flooded around Mission Hill
looking for this man who had killed Carol. Based on the evidence that they did have, they knew the shooter had used a
.38 caliber handgun, but there was really little else to go on aside from that. In a statement to reporters, one
investigator said, "There's no question the perpetrator thought they were police
officers." Investigators were convinced that the shooter lived in the Mission Hill
neighborhood and believed that he had committed similar crimes in the past. One investigator said, "Somebody in
Mission Hill's going to give this guy up. If not to do the right thing, then just because it will get rid of the
heat." Yeah. Because everybody was upset that there was a huge police presence in this area.
Yeah, of course. Meanwhile, the debate over what many saw as unequal protection was growing louder
and louder. Mayor Flynn dismissed the accusations, of course, that the Stuart case was getting more attention because
the victims were white. He said, "There will be the same aggressive and fair and
consistent enforcement of all our laws, regardless of where it takes place. Whatever area or color or ethnicity, it
will be handled the same aggressive and fair way by the Boston Police Department."
But, in the days that followed, other leaders at City Hall started speaking out with different opinions. David
Scondras, a white city councilor who represented the Mission Hill district, said, "You can't help but wonder if what
you're watching is a class situation. That it's all right for the poor to put up with an enormous amount of shootings
and killings, but presumably, if you're white, upper income, and suburban, maybe
that changes things. That's sad." Mhm. It is sad. It is. That's one way of describing it.
Yeah. Within a few days, a spokesperson for the Boston Police Department report reported, "The list of suspects has been
narrowed down to a chosen few." By that point, Chuck Stuart's story had changed somewhat, which prompted
investigators to adjust their search. Initially, when he described the shooting, Chuck made it sound like the
person had shot them because he thought they were police officers, but then he indicated that the shooter
only said something about there being 5-0. So, he was like it like they were like, "Hmm."
Right. And he said that the shooter said this after Chuck said he didn't have a wallet. Based on the revised statement,
investigators now thought the man maybe never saw the car phone and quote, "Was probably going to steal the car, but
panicked when he when his demand for the wallet could not be met." Okay. So, interesting.
Interesante. Yeah. Despite their insistence that the case was progressing well, within a few
days the decreased police activity in Mission Hill had become pretty noticeable, and so had the lack of new
information coming from the Boston Police Department spokespeople. Finally, on October 28th, police
arrested their main suspect in the case, 29-year-old Alan Swanson, who had been in custody for days actually already
after being arrested on an unrelated robbery charge. By the time he was arrested for the Stuart shooting,
Swanson had already been cleared of the other charge, so he he hadn't even done that.
Yeah. Which led many to question why he was still being held. According to Swanson's
attorney, Leslie Harris, the Boston Police Department was using Swanson as a quote, "Convenient scapegoat to appease
the public that the police were making progress in the Stuart shooting case, which they weren't."
Which they weren't making progress is what I mean. They very much were using him as a scapegoat.
For sure. Leslie Harris and others were right to question the legality of holding Alan
Swanson for a crime when they had literally not a single shred of evidence against him.
That's wild. And just a few days after his arrest, he was cleared of any involvement after
investigators became convinced he didn't know anything about the murder. So, they
just That's [ __ ] up. terrorized that poor guy. Yeah, they just terrorized him. He was
arrested uh for something he didn't do anyways and then was held for another thing he didn't do.
thing that he didn't do and they had no evidence of him doing it at all. Yeah. I'd call that uh racist.
Yeah, I would too. Yeah. So, the arrest and release of Alan Swanson uh made police look pretty bad.
Yeah. But, any anger over his arrest was quickly overshadowed on November 9th when news broke that Chuck and Carol's
baby, who they had named Christopher, died of complications from his premature birth.
Oh, that's so sad. sad. Christopher's death put even more pressure on investigators to find the
killer and at the same time raised questions as to whether his death would be added to the charges when the killer
was caught. Yeah. That's two murders. Yep. They did happen in Lacey Peterson. Yes, yeah.
Uh speaking on behalf of the district attorney's office, chief homicide investigator Francis O'Meara told
reporters, "If and when the DA determines it's a homicide and if and when somebody is arrested, they will be
charged with two complaints of homicide." Damn. Which I think is fair. Yeah. I think absolutely.
Cuz that baby was alive. Yep. Like they delivered that child, which is remarkable.
Truly remarkable to me. And really like just horrifying to think about. Yeah. Um but it's like that baby was born and
is alive Yeah. and died because of what happened. of the murder of their mother.
Yeah. Like that is directly linked. That's killing two people. Yeah. Easy. It's just one of them just
happened to live longer, you know? Exactly. when you shoot somebody and like they're
in a coma but then they die, you know? It's still murder. Yep. So, it turned out the public wouldn't
have to wait very long for news of yet another arrest. Just 2 days later, police arrested 39-year-old Willie
Bennett during a traffic stop. And he was soon charged with the murders. Jesus. A traffic stop escalated
to murder. Wow. Got it. At the time of the shooting, he was a resident of a housing project near the
crime scene, and he resembled the wildly vague description of the shooter, and he
was also known to police. In 1982, he was convicted of assaulting an officer when he pointed a gun at a Boston police
officer and removed the man's gun from his belt, which he then used to shoot out one of the tires on the police
cruiser. Damn. When police got to his apartment, they found him crouched on the floor of his living room clutching a
revolver, and he reportedly told police, "You're not going to take me alive." One
of the arresting officers shot him in the hand, which forced him to drop the gun, and at that point he was taken into
custody. Okay. So, that's the story of his life. Wild ride. Yes. According to the report at the time
of his arrest, Bennett admitted his involvement in the shooting of the Stewarts during conversations with
police. Huh. And witnesses reported seeing him wearing a similar outfit to that uh to
the one that Chuck described, which was a tracksuit. Yeah. A just a general tracksuit.
I'm like, which is a um we're in Aren't we in the uh '80s here? Yeah. Yeah. So, uh
But it actually of people are running around in a tracksuit. A lot of people were, but I'm not sure
about Willie Bennett. Hm. That said, Bennett's relatives denied that he owned any clothing matching the
description of the shooter, and investigators weren't able to find anything that resembled it during their
search of his apartment. Wow. So, what did he do with it? Exactly. Despite the now lack of evidence, which
is coming up again, police were convinced of Bennett's guilt, and in his statement to the press, Assistant
District Attorney Louis uh Sabadini described Bennett as a quote mad dog running amok with a horrendous 21-year
record of violent crimes. Get it together. All right. Like cuz the thing is here, you're like you'd
it would look better like you would understand like police you know, you want the police to go hard at this. A
woman was shot A pregnant woman was shot in the face and her baby has now died. Yeah.
It's like of course you want them to find who did this, but it's like but it's like we want you to find who did
it. And and there's no one looking at the guy in the car. Right. Like that wasn't even a thought.
When is nobody looking at the guy in the car who only got shot in the stomach? That's the
thing. I'm like why would she be shot in the face and he wouldn't? Right. Why Why are they potentially leaving
someone alive? Exactly. If they're going to carjack you and their plan is to kill both of you and
they shoot one of you in the head and the other in the stomach it doesn't make a lot of sense.
in the head. And even from a logistics standpoint, how did they got in the car or were they
standing outside of the car? He doesn't even really say. And that's the thing. It's like I
you can understand the like need to catch whoever did this because shooting a pregnant woman is a wild heinous
crime. Yep. But like they're just they're leaning right into the the racist thing here and
it's like that's and and it's a bummer. It is a bummer. Cuz it's like you really were doing
bad police work. I think it was a though have done really good police work. I love Boston more than anything about
being from here, but I think it was a very bad time for Of course. Yeah, like I mean hey, you
got to be able to admit when when you know There was a lot of your town and admit its faults.
Yeah, there was a lot of racism running deep. Yeah. Absolutely. You know. But because they lacked sufficient
evidence to charge Willie Bennett with the murders, authorities took their case to a grand jury in mid-November. Which
I'm like why would you take it to a grand jury if you don't have any evidence? That's weird. But in the
meantime they were still able to hold him on an unrelated robbery charge from a few weeks before the Stewart shooting.
They're just grasping at straws here. Yeah. A week later Chuck Stuart had recovered
enough to speak with the police officers a second time. Yay. This was when he was shown pictures of
potential suspects and asked whether he recognized any of the men in the photos.
According to a spokesperson for the BPD, Chuck had a strong physical reaction when shown photos of Bennett, but he
wasn't able to make a conclusive identification at the time. Okay. I know how this ends now. That's why I'm
being very flippant about this. Yeah, exactly. I think everybody else, too. Yeah.
What constitutes a strong physical Well, that's what I want to know. I want to know what kind of shenanigans
Yeah. What's happening there? And I don't know. There's a There's a lot of questions I have that I think I'll keep
to myself. Well, while Chuck's reaction seemed like a step in the right direction for the police, otherwise the
investigation was running into trouble. By the end of November, police still had
yet to find any evidence linking Willie Bennett to these murders. Awesome. His family and friends were becoming
increasingly vocal in their belief that, like Alan Swanson before him, Willie was
being scapegoated. Yeah. Just to appease the public and, you know, make the police look good.
Yeah. By his own admission, Chuck Stuart said he never got a good look at the man who
shot his wife, but he was convinced that he could identify the person if he saw them in a lineup.
Makes That makes sense. For me, those two things feel like they are They're very conflicting ideas.
They're very conflicting here. I I don't understand how that works. Yeah, the thing is like I didn't get a
good look at the guy, but like if you put a lineup, I I could probably I could definitely say.
But if you tell me who you want to put behind bars, I can totally point at them.
Like I can absolutely do that. That's good. Cool. That's awesome. And he said he could do
this based largely on the fact that the shooter had a very distinct voice. Mhm. "Wow."
Okay. Wow. Okay. You're doubling down there. Like them. In late December, after Chuck was
released from the hospital, a judge ordered Willie Bennett to appear in said lineup, and Chuck told investigators
that Willie, quote, "Looked most like the man who shot him and his wife." Cool. Not definitely was, but he looks
the most like him. Looks the most like him, I'd say. One source went a step further telling a
reporter that quote, "Stewart made additional comments during the lineup that convinced investigators it was
absolutely crystal clear. That's the guy." Okay. Okay, media. Sure. Later, it would come out that one of the
main reasons for Willie Bennett's arrest was that his nephew, a 15-year-old at the time, was bragging to his friends
that his uncle was the shooter in the case. However, the nephew would go on to deny
that. So, who knows? Okay. But, the rumor was then apparently spread to others around the
neighborhood, which was eventually how it made its way to a Boston police officer, and that became the impetus for
Willie Bennett's arrest. Okay. In all reality though, the case against him was weak based on hearsay probably
from a group of teenagers and only supported by a violent criminal history. Yeah.
But, across the river in Revere, another story was coming together and it told a
very different version of what happened to Carol Stuart that night in Mission Hill.
From the moment Carol and Chuck's friends heard about the shooting, a lot of them flashed back to the various
comments that they had all made in the past. Ooh. Remember, they didn't think something
was right about Chuck. Yeah. For Chuck's friends, it was comments about Debbie Allen and how much he
wished something bad would happen to his wife. He literally said that to his friends.
Wow. He really liked Debbie and it was just too bad that nothing bad was happening
to Carol to make that work. Man, just divorce your wife. It's really like I know it sucks to go
through. I'm sure a divorce is suck. Of course they do. But, I don't even think It is far superior to murdering someone.
Far superior. yeah. I don't even think it's the fact that like divorces suck and it's a lot
to get through. I think for Chuck, he didn't want to be seen as somebody who had a divorce in their past.
Yeah. That's absolutely it. He could gain sympathy from a wife who was shot and killed while pregnant.
Yep. But for Carol's friends, it was how unbelievable it was that Carol would have found herself in that neighborhood
given her profound fear for quote urban violence. She had a a big fear of shootings.
Okay. There were also other holes in Chuck's story and the fact that he changed his
description of the shooter. After all, if things happened as he had described them, why was there no
evidence to support everything he said happened? Yeah. And in hindsight, there would be other
oddities, too, like the dispatcher who remembered Chuck's final question before the line disconnected. "Have you gotten
any calls from the press yet?" Wow. Okay. What? What? What? What? I'm going to spell this out for you
guys. He shot his wife, obviously. the end of this is he did it, my friends. you all saw that coming.
Yeah. "Have you got any calls from the press yet?" while he's sitting next to calls from the press
that he just shot in the head with a baby in her stomach. Wow. Yeah. Okay. Yeah, that's wild.
Okay. That is wild. And just like, I'm like, how are you that [ __ ] dumb to even say that?
That's the thing. And why in hindsight was that weird? I'm glad that he's an idiot, so
Same. Of course, nobody wanted to believe that any part of the story was a lie. They had both been shot and even
though Chuck didn't die, he did suffer serious injuries and lost his wife and his baby, everyone thought. It also
seemed too unbelievable to be true and the official story seemed more plausible to everybody.
Yeah. But everyone from the coroner to members of the press had unanswered questions
and eventually that feeling of having missed something would make a lot more sense.
Ah. Whether people wanted to believe the official story of the carjacking or not,
the case against Willie Bennett was clearly unraveling, going nowhere, and there were no alternative suspects.
Then, on January 2nd, 1990, Chuck's brother Matthew walked into a Revere Police Department with a very strange,
tragic story to tell. Oh, yes. According to Matthew, Chuck had approached him a few weeks before the
shooting with a proposition. He had a plan to steal Carol's jewelry from their house to commit insurance fraud.
When that strategy didn't go as planned, Chuck concocted a new scheme, and he said all he needed Matthew to do was to
meet him in Mission Hill at a specified time to receive a bag and get rid of it in a place where it would never be
found. This is horrifying. Thinking his brother was still trying to pull off the insurance scam, Matthew
agreed to help assuming the bag would contain jewelry or some other valuables like that. Still wrong, but not quite as
deep. Yeah. Matthew confessed that he met Chuck in Mission Hill that very night, where he
received what was eventually identified as Carol's purse. Inside, he found a .38 caliber handgun
and his and some jewelry. He admitted to keeping Carol's wedding ring for himself.
She's like, "Wow." What? Man. And he said the rest he took to his friend John McMahon, and the two men
brought the items to a railroad bridge in Revere and tossed them into the water.
The gun, it turned out, had been stolen from the Caucus and Sons safe a few days
before the murders occurred. So, he stole the gun from work. Holy [ __ ] Matthew Stuart insisted that and he also
has always maintained that he knew nothing about Chuck's plan to kill Carol, and if he had, he never would
have gone through with any of it. Okay. But now it made sense why that case against Willie Bennett never made sense.
Yep. It was because the real killer was staring everyone in the [ __ ] face for months, and no one wanted to be the one
to suggest what had already crossed everybody's minds. Wow. Unfortunately, Carol's real real killer,
her husband Chuck, would never be brought to justice though. Nope. The day after Matthew Stewart went to
the police with his story, Chuck drove his car to the highest point of the Tobin Bridge,
got out and threw himself to his death a little after 7:00 a.m. I have thought about this so many times
going over the Tobin. Because if you live near here and you go like anywhere, you're you've gone over the
You're going over the Tobin. times in your life. The fact that he threw himself off the
Tobin. Spooky as hell. It is. It really is. A few hours after he was seen jumping
from the bridge, divers found Chuck's body in the Charles River, which is not a place you want to die.
You do not want to die in the Charles. On the passenger seat of the car though, investigators found a note that read,
"To my family and friends, I love you very much. Thank you for standing beside me. My life has been nothing but a
battle for the last 4 months. Whatever this new accusation is, it has beaten me. I've been sapped of my strength."
That's it. Okay. That's all it said. Yeah. It made no mention of having murdered
Carol or her death at all. But authorities believed that he had killed himself rather than face
consequences of having murdered his wife and unborn son. Jesus. Because Chuck gave no explanation for
his suicide and never really confessed to murdering Carol, the official motive remains a mystery, but there's obviously
reason to believe that he wanted to kill Carol so he could collect on a $500,000
insurance payout. My god. And that money would have allowed him to pay down his debts and open up the
restaurant that he dreamed of and once single, he could pursue a relationship with other women
Wow. and gain the sympathy that he had lost a wife so violently. Wow. A few days later, investigators dragged
the river where Matthew claimed to have discarded the gun and Carol's purse, which was located and determined to be a
match for that gun that was stolen. Wow. And a match uh for the gun that was obviously used in the murder.
Yeah. That night investigators held a press conference to announce that they believed Chuck Stuart was the killer and
that the case would soon be closed. Holy [ __ ] The following year, Matthew Stuart and
Jack McMahon were indicted on charges including conspiracy to commit murder, unlawful possession of a firearm, and
compounding a felony. And at the same time, Willie Bennett was finally cleared on murder charges, but
he was still found guilty on armed robbery charges stemming from that unrelated case.
Later that year, Matthew and Jack pleaded guilty to the charges related to their involvement in the case.
In the years since the murder of Carol and Christopher Stuart has become one of the most defining criminal cases in
Boston's more recent history. Yeah. There were, of course, obviously the original victims, Carol and Christopher
Stuart, but the fallout from the case and the way that it was handled by investigators was felt by so many
residents, some who had never even heard of Carol. And people who hadn't done anything
wrong. Yeah. After the announcement of Chuck's death, considerable public outcry led the US
Attorney's Office to open an investigation into the mishandling of this case. Oh, damn.
And claims of racial bias against the Boston Police Department as well. After a 15-month investigation, US Attorney
Wayne Budd announced they have uh they had found quote some evidence of serious misconduct, but not enough to
justifiably pursue charges against any of the officers involved. Wow. So, he was like, "Yeah, we did find some
evidence of serious misconduct, but we're not going to do anything about it." though.
He said, "I will not prosecute unless I think a a person can be found guilty by an unbiased jury."
Damn. Okay. Okay. At a press conference in 2019, years and years and years later, Suffolk County
District Attorney Rachael Rollins spoke out about the ways that the Stuart case tore the city apart and left lasting
wounds that would remain unhealed. She said, "Today we remember the survivors. Those survivors include several families
and the entire Mission Hill community. The brutal murder of Carol and Christopher Damato precipitated a chain
of events that created deep trauma beyond one family. The people of Mission Hill, especially black men, were treated
like criminals rather than members of a community that like all of us are innocent until proven guilty and who the
police are allegedly duty-bound to protect and serve." Yeah. Which is like gives you chills
Yeah, you like hell yeah. She and other city letter leaders as well as residents of all the
neighborhoods looked forward to a day when justice and protection would be applied equally, which as she pointed
out can only be achieved by confronting the wrongs of the past and holding ourselves to higher moral standards.
Hell yeah. Which I think is a great way to end that. Absolutely. You know, ha hold yourself to a higher
moral standard. Yes, absolutely as we all should. Don't be a racist. Don't be a racist.
Don't be a racist. And don't be a murderer. Don't be a murderer. Don't be a [ __ ] [ __ ]
If you don't want to be with somebody then don't be with them. Don't be with them.
It's that simple but let them go live their life. You don't need to like Ugh, it's just so yucky.
It really is. It's so yucky when somebody's like, "You know what? Instead of just like making
things a little uncomfortable for a while and ending this relationship kill this person.
remove this person's ability to have any further life experiences. know how anybody kills anybody but
specifically killing a pregnant woman Yeah. is like another level of just depravity.
Truly. Like and for him to do that to his own child is sick. It's unthinkable. It is unthinkable.
It's so messed up. But that is a very famous case from Boston. So if you're around here
that point I said, "Oh, I know exactly what this is." As soon as he parked that car
For some reason that the name didn't stick in my head but yeah, that definitely brought it.
Yeah, then I didn't recognize the name at first either and then I was like, "Oh."
So, yeah. Yeah. Terrible, terrible case. Really terrible. It's just really awful.
It is. And I just really I feel so bad for Carol. I do, too. Carol had a lot to offer.
She had a lot to offer and she a lot to give. good friend. She was a hard worker.
Smart as hell. She seemed like she was going to be a great mom. And that's all she wanted was a family.
That's the thing. When you want it that badly, you're going to do a great job at it.
Yeah, I agree. And she was never given that chance and that really sucks. I know.
Poor Christopher. I hope that her and Christopher are like somewhere together. You know.
In another life. With a better dog. just be be good people. Be good people to your fellow people. Especially right
now. My god. people to your fellow people. Yeah. Let's stop being dicks to each other.
people to to everybody. Yeah. To to real to people in life, to people on the internet, to all the things. Just
don't don't be dicks. Yeah. That's a great takeaway. It is. Just don't be dicks.
You know. And if you take nothing else away, we hope you keep listening. And we hope you
keep it weird. But not as weird as that [ __ ] cuz he's a freak. Cuz [ __ ] that guy.
Hate him. Mhm.

On the night of October 23, 1989, Charles and Carol Stuart were returning home from a childbirth class and drove through the Roxbury neighborhood of Boston. According to Charles Stuart, they were stopped at a red light when a black teenager forced the driver’s door open and robbed the couple, then shot Charles and Carol before running off. Charles managed to call 911 from his car phone, but by the time emergency responders arrived, Carol was in a very bad state and would die a few hours later at a nearby hospital.

The murder of Carol Stuart captured the attention of residents in and around Boston, and the story remained on the front pages in the weeks that followed. On one hand, it was a tragic story of a young couple on the verge of starting a family who were robbed of a future. On the other hand, it shined a bright spotlight on the city’s long-simmer racial tensions and the unequal treatment and application of law enforcement with regard to race. And those tensions would be significantly exacerbated when the truth about Carol Stuart’s murder was finally discovered.

Thank you to the Incredible Dave White of Bring Me the Axe Podcast for research and Writing support!

References Brelis, Matthew. 1989. "Stuart suspect held on charges." Boston Globe, November 12: 1.

Canellos, Peter. 1989. "Roxbury probe is criticized." Boston Globe, November 1: 29.

Canellos, Peter, and Irene Sege. 1989. "Couple shot after leaving hospital; baby delivered." Boston Globe, October 24.

Cullen, Kevin. 1989. "Stuart suspect linked to Brookline case." Boston Globe, November 13: 1.

Hayes, Constance L. 1990. "Illusion and tragedy coexist after a couple dies." New York Times, January 7.

Howe, Peter, and Jerry Thomas. 1989. "Reading woman dies after shooting in car." Boston Globe, October 25.

Howe, Peter, Kevin Cullen, and Anthony Flint. 1990. "Police focus on brother, woman." Boston Globe, January 8: 1.

Jacobs, Sally. 1989. "Stuart is said to pick out suspect." Boston Globe, December 29: 1.

—. 1989. "Stuart reportedly reacted physically to suspect's picture." Boston Globe, November 23: 93.

Jacobs, Sally, and Diego Ribadeneira. 1989. "No wallet, so killer opened fire." Boston Globe, October 26: 1.

Koh, Elizabeth. 2023. "Stuart shooting timeline." Boston Globe, December 1.

Kong, Dolores, and Sally Jacobs. 1989. "Infant of shooting victims dies of respiratory failure." Boston Globe, November 10: 1.

Murphy, Sean. 1989. "Man questioned in shooting still held." Boston Globe, November 7: 17.

New York Times. 1991. "U.S. won't indict Boston policemen." New York Times, July 5: D7.

Rollins, Rachel. 2019. "30 years after Stuart case, Boston still healing." Commonwealth Beacon, November 9.

Sharkey, Joe. 2015. Deadly Greed: The Riveting True Story of the Stuart Murder Case. New York, NY: Simon and Schuster.

Walker, Adrian, Evan Allen, Elizabeth Koh, Andrew Ryan, Kristin Nelson, and Brendan McCarthy. 2023. "The untold story of the Charles and Carol Stuart shooting." Boston Globe, December 1.

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Brief Summary

The episode discusses Carol Stuart's murder, Chuck's involvement, and the investigation's racial tensions.

Key points

Introducing Carol Stuart. Carol Stuart was a bright student with dreams of a happy family.
Chuck's Lies. Chuck Stewart misrepresented his education and background to impress Carol.
The Complexity of Love. Carol's relationship with Chuck was filled with affection but also tension.
The Perfect Suburban Couple. Carol and Chuck's marriage appears ideal, but doubts linger beneath the surface.
Chuck's Materialism Raises Concerns. Chuck's spending habits and materialism become a point of contention in their relationship.
The Affair Begins. Chuck's interest in a summer employee complicates his marriage with Carol.

Episode highlights

Episode quotes

Holy [ __ ].

5:52WatchMay 12, 2025

Tension

85/ 100High tension

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