World's Most Evil Killers - Season 5, Episode 19 - Richard Roszkowski - Full Episode | Forensic Files

NARRATOR: On the 7th of September 2006, three people were gunned down on a street in the city
of Bridgeport in Connecticut. The youngest victim, nine-year-old Kylie Flannery,
had been chased down by the lone gunman and executed at close range. All of this unfolded in a matter of minutes,
so for anybody witnessing this, it must have been like watching a scene from a movie play out
but knowing that it's all too real at the same time. The killer was 41-year-old Richard Roszkowski
whose infatuation with Kylie's mother, Holly Flannery had come to a head in the most tragic of circumstances.
Even though Holly Flannery was clearly in some fear of Richard Roszkowski, I don't think, for one moment,
she could have imagined that would effectively mean the end of her life and her daughter's.
NARRATOR: Roszkowski was eventually sentenced to death for killing Kylie and given life sentences for the murders
of her mother Holly and tree surgeon Tommy Gaudet, a man with no connection to the Flannerys.
EILEEN POTKAY: Roszkowski, he's absolutely evil. I hate him, and I'm glad that I never
have to be in the same room ever again with him. NARRATOR: Richard Roszkowski had emerged as one of the world's
most evil killers. [MUSIC PLAYING] In May 2009, 44-year-old Richard Roszkowski was sentenced to death for the murder
of three people in a short yet bloody killing spree 2 and 1/2 years previously. His youngest victim, Kylie Flannery,
was just nine years old. The twisted killer had become fixated with Kylie's mother, Holly.
It was an obsession that led to tragedy, which played out just after 9:00 AM on a quiet sunny morning
in Connecticut. Local news reporter Daniel Tepfer was one of the first journalists at the scene.
DANIEL TEPFER: It's a case I'll never forget. I, actually, was on my way to work that morning
when I got a call to get over to Seaview Avenue, and I got there. The police were still there.
They were still interviewing witnesses. And I started talking to some of the witnesses there,
and I was just appalled at what they were telling me had occurred. And these are things that will stay with me forever.
NARRATOR: At his trial, Roszkowski claimed to be insane and in a drug-induced haze
during the killing spree. The prosecution team of C. Robert Satti Jr. and Margaret E. Kelley helped put him behind bars.
I've been doing this for a long period of time, actually 40 years. What was especially difficult in this case
was the fact that he executed Kylie in the manner in which he executed her, shooting her once until she fell
and then walking up to her and giving her the coup de grace, killing her. MARGARET KELLEY: It opens your eyes to the fact
that in the blink of an eye, things can change. And I remember it being a beautiful day,
and here's a young girl going to school with her mother. Next thing you know, there are three people dead,
and I'm sure that for the people that were in the area at the time and what they may have seen
or heard or witnessed, it's just how things can tragically change in just a split second.
NARRATOR: During a second trial in 2014, Roszkowski would show a remorseful side,
but behind the facade lay a deadly killer. He had been sent to the state's maximum security
mental hospital sometime after his arrest, and the head of the hospital who's dealt with the worst of the worst called the judge
and said, could you please take him out here? We can't handle him. He's too dangerous for us.
That might give you an idea of the kind of person that Richard Roszkowski is, cold-blooded, no moral compass,
no conscience. NARRATOR: This killer story begins in January 1965. All we know about Richard Roszkowski's background
is what he told the authorities after his arrest. Roszkowski was born in the US, and the information about
his background is quite patchy. And we're quite reliant on the things that he said about it, so we did have to take it
with a bit of a pinch of salt. But one of the things that he says is that his father
didn't really bother with him. He felt that his father was quite distant. From what I remember, not a good student in school, got
involved in drugs early on, was rarely in school later on, and he used to get in trouble--
little things, thefts and vandalism and that kind of thing. NARRATOR: At a very young age, Roszkowski and his family
visited his mother's homeland, Poland, which he says is where his troubles with substance abuse
began. Roszkowski claims that he first tasted alcohol when he was around five or six years old.
And then, when he was 10, he started misusing substances, like marijuana and glue sniffing,
and that then progressed on to other things. GEOFFREY WANSELL: Glue sniffing leads to cannabis.
Cannabis leads to cocaine. Cocaine leads to heroin. That all leads to a drug problem,
and we're now still only a teenager. NARRATOR: Roszkowski was small in stature, something that led to him being picked
on during his formative years. Roszkowski claims that his family moved to a new area
during his childhood, and this area was quite deprived. It was quite poverty-stricken, and it
was an area where there was quite a lot of criminal activity going on. And he claims that he was bullied by the local children
in the area, and then later on, the people who had bullied him forced him to join some kind of gang.
So again, we've got all of these external factors that are compelling me to behave in a particular way.
NARRATOR: Life didn't get any easier for Roszkowski. He struggled with his drug addiction
and couldn't hold down a regular job. Roszkowski lived quite a transient life as an adult.
He flitted from job to job. If you think of the impacts on that, Roszkowski doesn't have this consistent group of people
around him, either colleagues or neighbors, who act as a bit of an informal check on our behavior.
So he is off the radar, in many senses of the term. NARRATOR: Roszkowski's mother had a house on Trojan Drive
in Bridgeport, Connecticut, and her son would sporadically live with her. During this time, he got to know another resident
on the street, Holly Flannery. ELIZABETH YARDLEY: She got to know Roszkowski's mother quite
well and spent quite a lot of time at her house, and she gets to know Roszkowski through his mother.
And I think because of the kind of person Holly was, I think she probably showed
him some kindness and some empathy and some compassion. NARRATOR: Holly Flannery lived on Trojan
Drive with her husband and her daughter Kylie. But according to witness testimony from the case,
Holly and Roszkowski became close in the early 2000s. On the surface, Holly seemed to be
a really wonderful person, a good mother, a great wife. She did everything that you would think is a normal mother
and a housewife would do, but below the surface, there was something dark there.
It was something that would cause her to be attracted to Richard Roszkowski. NARRATOR: By 2004, Roszkowski was serving three
years in prison for burglary. Court documents show that Holly would visit and speak
with him on the phone. Holly did correspond with Roszkowski in prison, and I think this came from a place of kindness
and a place of concern. I think she believed he was somebody who'd had several disadvantages in life,
and she was acting out of friendship to him. But in terms of the way he interpreted her kindness,
he became fixated with her. He became obsessed with her, and it didn't take long before Holly started to become actually
quite fearful of this man. NARRATOR: In a letter Holly wrote to a friend in January 2004, she stated that she'd
spoken to Roszkowski over the phone while he was still in prison. She said that she'd been threatened by him
and was told she was going to go off a cliff. Chillingly, she added, if I should turn up dead,
tell Kylie I loved her. [MUSIC PLAYING] When Roszkowski is released from prison in 2005,
he moves in with his elderly mother, so he is in Holly's daily life. She sees him day in, day out, going about her business.
And I think this is the point at which his fixation and obsession with her intensifies,
and some of his behavior towards her starts to be quite concerning. It was obvious, at some point, that she realized that he was
completely out of control, that she had no longer could control him, and he had become a threat not
only to her, but her daughter who she worried much more about. NARRATOR: In case files, Holly's friends
stated that she appeared more anxious and was afraid of her obsessive neighbor. At one point, Roszkowski broke into Holly's house
and threatened her with a gun. GEOFFREY WANSELL: I doubt very much whether she encouraged it,
but like all stalkers, they don't pay attention to reason. They act irrationally, and no one could demonstrate that more
accurately than Roszkowski. There was one particular incident in July 2006 where Holly said that Roszkowski had pinned down and shaved
some of her hair off. And he said to her that he wanted to basically mess up her hair, so no other man would want her.
So at this point in time, his behavior has crossed the line to physical violence.
He may have been following her before. He may have been spying on her, but now, he's actually
physically harming her. So he thinks that Holly is his possession. He thinks that he owns her, and this is
a really dangerous place to be. [MUSIC PLAYING] NARRATOR: Richard Roszkowski had grown
completely obsessed with his former neighbor, 39-year-old Holly Flannery. The ex prisoner and ne'er-do-well was known
to the authorities, but there appeared to be no reason for concern. DANIEL TEPFER: He had a number of arrests for drugs or thefts.
He was flying below the radar. He was the kind of person that you wouldn't even generally give notice to.
He's just someone-- someone in the crowd, I guess. NARRATOR: Roszkowski's mother had moved away
from Trojan Drive, and the 41-year-old was now living a transient life around Bridgeport, Connecticut.
He'd previously been staying in lodgings on nearby Seaview Avenue. MARGARET KELLEY: He was living in this rooming house
with some other individuals. There was some testimony during the trials from one of the individuals that there was a drug use going on.
NARRATOR: Not all of the tenants at the house on Seaview Avenue were criminals. Just before Roszkowski had been asked to leave by the landlord,
he'd crossed paths with a 38-year-old tree surgeon named Tommy Gaudet. He'd been living in this rooming house on Seaview Avenue
with other people who had been working at the landscaping company. He had been separated from his family
and was hoping to turn his life around and get back to them. ELIZABETH YARDLEY: So their paths had crossed,
and they knew of each other. But I think in the brief time that they have instructed,
Tommy had clocked that Roszkowski was not a nice individual. He had noticed that he was unpredictable,
and he was the kind of person to give a wide berth to. NARRATOR: Tommy Gaudet had two children
who meant the world to him, which his sister Eileen Potkay testifies to. EILEEN POTKAY: Oh, my God.
You know what? I'm actually getting goose bumps just thinking about it. When my niece was born, it was probably
one of the most wonderful days of his life to have a baby girl, and he was hands on.
He changed her diaper. He fed her. He burped her. He went shopping for her clothes.
When he became a father, he was an amazing dad to Natasha. And it was many years later that he
had a son, so Natasha was alone for many years with Mommy and Daddy. But my brother was a very hands on dad, and he adored her.
NARRATOR: In September 2006, Thomas Jr. was 10, and Natasha was 14. NATASHA GAUDET: I remember going in his cherry picker.
He was a tree man. And he worked for a tree company, and he used to have this big truck with--
like the firemen have, like the big bucket on top. And I remember going in there, and, you know, feeling
like I was on top of the world. THJOMAS GAUDET JR.: My dad was a great dad. He made sure that we were always having
the best time as possible. I think, him growing up, he didn't have the best father
figure, so he definitely wanted to make sure that his children had, you know, so
much better than what he had. The last time I spoke to my dad, I was in the driveway hanging out,
and he stopped by and said, hello. And that was the last time I saw him. NARRATOR: Tommy Gaudet got up for work
on the 7th of September 2006, but he never made it that far. At some point during the morning,
Tommy and Richard Roszkowski had a heated exchange over the phone. Roszkowski phones Tommy and basically,
accuses him of having a relationship with Holly. And Tommy just thinks this guy has lost it.
He remembers Roszkowski his behavior and just thought, oh, this is just him kicking off again.
NARRATOR: Three miles across town on Trojan Drive, Holly Flannery was getting her nine-year-old daughter
Kylie ready for the first day at her new school. DANIEL TEPFER: According to testimony at trial,
it had started out as a very normal morning. Holly had gotten Kylie up to get ready to go
to Thomas Hooker School. NARRATOR: But the nine-year-old would never make it to school.
Holly and Kylie's 41-year-old former neighbor had finally snapped. After months of intimidation, Richard Roszkowski
was about to put his deadly threats into practice. Roszkowski went into a rage, a rage
that most people certainly wouldn't be able to understand, and I don't understand.
But he somehow imagined that Holly was cheating on him. She had broken off their relationship,
and he was determined to confront the man he believes she was cheating with. NARRATOR: Somewhere in Roszkowski addled mind,
he believed that Holly and Tommy Gaudet, who were strangers to one another, were in a relationship.
It has never been established under what circumstances the trio traveled to Seaview Avenue,
although Holly's car was eventually recovered from the scene. But just after 9:00 AM, Roszkowski,
Holly Flannery, and her daughter Kylie arrived at the boarding house. Now, in terms of Roszkowski thinking,
he was like a missile at this point. Here is a man who is very fixed and very rigid in his thinking.
He's decided that he's going to kill Tommy on this day, and that is exactly what he follows through.
DANIEL TEPFER: He was just standing outside the house. He was just simply just standing there, outside this rooming
house when Roszkowski decided, for whatever reason was going through his head, that Gaudet must
be the man that she was cheating with even though they had never even met. NARRATOR: One thing we can be sure of is, at some point,
Richard Roszkowski pulled out a gun. Gaudet yelled at him. Like, what is going on here?
Hey, what's going on? And was immediately shot in the head. But once Gaudet is dead, it's as if the lock is taken off
Roszkowski's self-control, and he grabs Holly Flannery in a headlock on the street, in front of her daughter Kylie,
puts his arm around his head, and Holly's shouting, screaming. She started screaming, not in front of my daughter,
not in front of my daughter. He then shot her once in the head. She falls to the ground.
And then, poor Kylie just doesn't know what on Earth is going on, and trying to make sense of it,
she runs for her life. He then runs after her, catches up with her, shoots her in the back, causing her to fall down
on the sidewalk on her back. She's face up, screaming, crying. He then walks and stands right over her and fires
into her face. NARRATOR: In less than three minutes, Tommy Gaudet and Holly Flannery had been shot dead,
and Kylie Flannery was fighting for her life. The nine-year-old who'd meant to be starting a new school
that morning had been chased along a suburban street and shot three times at close range by Richard Roszkowski.
So Kylie is a 9-year-old girl. She's just seen her mother shot dead in front of her.
She's seen her mother's killer kill somebody else. So I think it's sheer terror in terms of what's
going through her mind. It's very difficult to process that amount of trauma and work out what on Earth is going on.
So her immediate reaction is to just get away, get out of there. The thought of that little girl, Kylie,
running down the street, her flip-flops flying off as she ran, scared to death, and then to be shot and laying
on the sidewalk face up when Roszkowski stood over her and fired the final shots, I can't even
imagine it had happened. NARRATOR: Paramedics rushed Kylie to a hospital, but her injuries were too severe.
Despite efforts by doctors to resuscitate the nine-year-old schoolgirl, they couldn't save her life.
GEOFFREY WANSELL: There could be no excuse for this. To take the life of a 9-year-old child lying at your feet whom
you've shot in the back and you decide to execute her effectively by shooting it twice in the head, that
is profoundly, profoundly wicked act, which I think does justify the use of the word "evil."
NARRATOR: Three people were now dead at the hands of Richard Roszkowski, and the drug-addicted killer
was on the run. His obsession with his 39-year-old former neighbor had led to tragedy.
Let there be no doubt that Roszkowski was erratic. Let there be no doubt that he'd always
lived on the edge of society and that he consoled himself with drugs and crime. The tragedy of this entire case is his fixation
on Holly Flannery, because without that, these killings would not have happened.
He decides on a course of action, and he literally just goes and carries it out.
So any time that morning on the way over to the boarding house, in between killing Tommy and Holly,
in between killing Holly and Kylie, he could have decided to stop. He could have decided not to kill anybody else,
but that was never going to happen, because he had a plan and he was going to follow it through.
NARRATOR: Detectives arrived at a scene of carnage. A beautiful sunny morning had been darkened by a killer
who remained unaccounted for. Police had no idea who it was and no idea if he was going to strike again.
After chasing nine-year-old Kylie down the street and shooting her at point-blank range,
Roszkowski had taken flight. GEOFFREY WANSELL: He doesn't run down the street. He runs through gardens, jumping over fences in an effort
to escape. Because it is 9 o'clock in the morning, in broad daylight, plenty of people out, and he's committed
three ruthless killings in a matter of moments in plain sight. This is not a man killing in private.
This is a man killing in full public view. Roszkowski flees on foot, taking clothing
from clothing lines on the way so that he can change his clothes and make it look like he's somebody else.
So he's got the presence of mind to do that. He also pulls over a motorist and offers
them some gas money to give him a lift to his mother's house. NARRATOR: While Roszkowski made his escape
in an unknowing stranger's vehicle, detectives were already onto him. The roommate of Tom Gaudet, who came out shortly
after the shooting, gave the name of a Richard Roszkowski, and he gave the police the location of his mother's
residence in Trum. NARRATOR: Roszkowski would not remain a fugitive for very long.
C. ROBERT SATTI: He was arrested in the town of Trumbull with the assistance of Trumbull police officials
who had set up at his mother's residence, what-- just happened to be at the dead end of the street,
so they were able to set up a perimeter. And Mr. Roszkowski just appeared to have no affect and emotion
at that particular time. NARRATOR: Across town, stunned journalists had started arriving at the bloodied sidewalks
of Seaview Avenue. DANIEL TEPFER: When I arrived at the scene, it appeared there was pandemonium.
People were all over the place. The police had blocked off most of the streets in the neighborhood.
They were out questioning people. I came upon a man sitting in a pickup truck. He was a landscaper, and he was just
sitting there, slumped over the steering wheel of his truck, obviously in distress.
So I went over to ask him, you know, what's going on? Well, as it turned out, he had been driving down
the street on Seaview and had seen, had seen the little girl getting shot, and it was just so upsetting to him that he had to pull over.
He couldn't drive anymore. I, then, went and talked to some other witnesses, all had similar accounts and all who were visibly distressed.
It's just something that it's very hard to comprehend. NARRATOR: The junction of Seaview Avenue and Boston
Avenue is a busy intersection during rush hour, and many passing motorists had witnessed
the very public murders. DANIEL TEPFER: One woman recalled hearing Holly Flannery scream, not in front of my daughter,
you know? She remembers hearing that but didn't really see that much. I mean, it was just-- everybody had little bits and pieces
of things that they had seen or they had heard, and you just had to kind of try to put together like a puzzle.
NARRATOR: Many of the witnesses described how calm Roszkowski appeared to be during the shooting.
This wasn't somebody who was losing it, who was going mad, who was on a rampage.
And it's very tempting to interpret his behavior in this way because of how close together
these murders were, but I think he knew exactly what he was doing. And if you listen to the witnesses describe it,
they talk about him walking and seemingly being unaffected by what he'd just done.
NARRATOR: The murder of three people, one of them a child, had completely shaken the community,
especially the people who turned up to help. C. ROBERT SATTI: It was testified too
that the ambulance driver and the medic was impacted very deeply because he had a child,
and it may well have been a daughter about the same age of Kylie. I do know, in talking to the law enforcement
officials that were there, it impacted all of them deeply. ELIZABETH YARDLEY: I think the impact on the local community
would have been immense. This is not the kind of place where multiple murder happens.
People would have just been going about their daily business, going to buy a paper,
taking the kids to school, getting their morning coffee, and in front of them, the scene of carnage emerges.
So I think it has left a scar on the community in terms of the feeling of safety and security in your own street,
in your own neighborhood, and the fact that people like this, they walk among us.
They often don't look like monsters, so it does make us question everybody around us.
NARRATOR: As investigators at the scene began to identify the victims, they reached out
to the family of Tommy Gaudet. EILEEN POTKAY: I got the phone call. And I was driving in the car, and I pulled over.
And they're telling me that my brother has been killed and that there was a woman and a child with it also,
and I just couldn't wrap my head around the fact that, how is this all connected?
And she just kept repeating it to me, that, you know, we're trying to put the pieces of this together
and that my brother had been leaving for work and was gunned down when he exited his door.
That's how I found out. I remember waking up to my mom on the phone, talking really loud saying, you know,
what are you talking about? This can't be happening. Let me walk outside. Thomas is sleeping, talking about me, and I was like,
what's going on? So me, as a curious 10-year-old, I decided to turn on the news,
and I saw, you know, the helicopter scene of the scene, you know? All they said was a, you know, three people have been killed,
and the aerial view of the house was where my dad lived. And I had recognized it because I had been there,
you know, just a few weeks prior, so I stumbled out of bed, went outside, found my mom and my sister in the driveway crying.
And I was like, what's going on? I know that my dad walked out of his house and got ambushed and shot in the head, and I don't know why.
That's all I know. [MUSIC PLAYING] NARRATOR: It appeared that Richard Roszkowski
had killed Tommy Gaudet because of misplaced jealousy and paranoia. There's a lot of different stories and theories
about what happened. I remember hearing, like, a lot of different lines. Like, it was a love triangle, a crime
of passion, just a bunch of crap, a bunch of mishmosh stories with no facts or evidence behind them but, I guess for the views--
ELIZABETH YARDLEY: Before the day of the murders, Holly and Tommy had never met one another.
They were not known to each other in any capacity whatsoever, and the only place that they had come together
was in Roszkowski's imagination. He had become so fixated on Holly, so obsessed with her
that he would sit and ruminate and think and make up scenarios in his head that he would
convince himself were real. [MUSIC PLAYING] NARRATOR: When Roszkowski's name was released to the public,
Thomas Jr., who was just 10 at the time, recognized his father's killer. When they put his mugshot on the news,
I immediately had a flashback to, you know, just a couple of months prior for my birthday
when my dad was visiting and came to give me a birthday card, and Richard actually drove him,
because they were roommates. So I immediately was like, oh, my gosh, mom. That's the guy who is dad's roommate,
and he gave me 20 bucks for my birthday. NARRATOR: Days after the shootings, the Gaudet family visited the crime scene on Seaview Avenue.
There were a lot of police officers, of course, a lot of bystanders, a lot of balloons, a lot of Teddy bears.
I didn't know if those were for Holly and my dad or if they were for Holly's daughter.
NATASHA GAUDET: He killed a 9-year-old little girl. She was a baby. My son is 10.
She was nine years old. I mean, not that it justifies my father or that-- Holly's death or anything like that or it
minimizes it, but to kill, to empty the clip in a little girl while she's running from you, that's, like, beyond evil.
I know this for 100% certain that if my brother had had the opportunity that day to protect that little girl
and save her life, he would have. He loved children. [MUSIC PLAYING] NARRATOR: Roszkowski told detectives
that he'd been gorging himself on drugs in the days and hours leading up to the murders, and he continued to claim to have
no memory of the incident. To my understanding, from what I hear and from what I know,
he was doing crack and heroin, and he was on a long drug binge that had been going
on for days, a lot of drugs. We're talking Xanax, marijuana, alcohol, heroin, crack.
We're talking a lot of drugs in his system. NARRATOR: As well as his out of control drug addiction,
detectives discovered Roszkowski's motive behind the murders. During the police investigation,
they learned of Roszkowski's rather transient, chaotic lifestyle, and they learned of his previous stints
in prison and his drug use. They also come to learn about Holly's experience, being victimized by Roszkowski, so the picture
starts to emerge of a man who feels entitled to behave in whatever way he wants.
He's very fixated. He's very rigid in his thinking, and he is self-obsessed. He is me, myself, and I. He has very little
concern for other people. [MUSIC PLAYING] NARRATOR: Just under three years later in May 2009,
44-year-old Richard Roszkowski went on trial at the superior court in Bridgeport, Connecticut.
He was charged with murdering Holly Flannery, her nine-year-old daughter Kylie, and tree surgeon Tommy Gaudet.
Tommy's family were in attendance throughout the hearing. I just remember seeing him and, you know,
asking my mom like, can he come out from behind there? Can, you know, he get us?
And, you know, of course, that's a fear. This person just killed your dad. Can they come and kill you next?
There were times where he was literally feet away from me, and that, you know-- that thought comes over you.
Like, wow. I can-- maybe I can get him, and it's almost like you want to attack him.
And it brings up something inside of you because you're-- you're just thinking he's so close to you,
but it's uncomfortable to be that close to a killer, a killer that could take two adults and a child's life
within three minutes. Three minutes, they're all dead. NARRATOR: Roszkowski claimed to have no recollection
of the murders and therefore, was not in control of his actions. The defense tries to claim that Roszkowski is insane,
and by implication, he's not responsible for his actions. And Roszkowski does play up to this.
So he exhibits some signs of shaking and stuttering in his speech and trying to appear
in a very stereotypical way to be somebody who is insane. NARRATOR: As well as a claim of insanity,
Roszkowski stated that he'd been on a drug binge that lasted for days in the lead up to the killings.
Supervisory assistant state's attorney C. Robert Satti Jr. led the prosecution. C. ROBERT SATTI: There was a substantial defense
that was put on. It took two different forms. One was a claim of intoxication, and the intoxication
went to the fact that Mr. Roszkowski, if the jury determined that he was intoxicated,
we had to disprove that and show that his intent was not going to be mitigated or actually, if he was intoxicated,
was an absolute defense of the crime. So I do recall that there was an intoxication claim being made,
and they put a lot of witnesses on concerning that. There was also a challenge as to the mental status
of Mr. Roszkowski. ELIZABETH YARDLEY: He was basically trying to say, this is not my fault, you know?
Poor me, look at me. I'm suffering from a terrible condition. But it was very clear in terms of his behavior
around the offenses that he did know what he was doing. He had a presence of mind.
He was constantly making decisions and making choices. Had he been legally insane, had he been suffering psychosis
or something like that, driving him to behave in a particular way, he would not have been anywhere
near as organized as he was. NARRATOR: Many of the witness statements from the day painted
a very different picture, that Roszkowski was calm and in control of his actions.
NATASHA GAUDET: Where he killed them, there was a light, and there was a row of cars.
So there were people who literally looked in the mirror and saw these people get shot and killed
and murdered through their rear view, that were testifying that day. DANIEL TEPFER: It was a tough testimony.
No question about it. It was tough for everyone in the courtroom to hear. I'm sure was tough for many of the witnesses
to testify about it. Some of them cried. Looked over at the jury, some of them were crying.
It was obviously something that they had never heard before, maybe never even imagined before, but now,
on top of it, they would have to hear to decide someone's guilt or innocence. NARRATOR: Ultimately, Roszkowski's plea of insanity
fell on deaf ears. I think the jury needed to understand that Mr. Roszkowski was responsible for his actions and knew
what he was doing when those three people were executed. We had argued that it was an extreme, cruel activity that
occurred in the killing of her that I suggest led to the finding of the jury that Mr. Roszkowski
deserved the death penalty. The verdict was guilty on the capital felony, and he was subsequently sentenced to death.
NARRATOR: But, in an agonizing twist for the victims' families, a legal technicality meant
the judge was forced to overturn the jury's decision. Roszkowski's conviction was upheld,
but a second sentencing trial would have to take place in the future. In December 2011, Roszkowski was interviewed in prison by
psychiatrist Dr. Howard Zonana. He still claimed to have no memory of the events.
NARRATOR: Roszkowski did, however, allude to a reason behind the killing spree. He claimed to have discovered a letter in his mother's home
on the morning of the 7th of September 2006. INTERVIEWER: Right. NARRATOR: No letter has ever been found by police
investigating the murders, and no link between Tommy Gaudet and Holly Flannery has ever been established.
Richard Roszkowski's resentencing trial took place in 2014, and this time, he was given the opportunity to speak
to the families of his victims. Like I said, is I'm truly, deeply remorseful for what happened, and I'm truly sorry for the pain
that I have caused to you and to all the family members. I am truly, truly sorry for your pain.
He says, I feel sorry. I feel remorse. And for me, that's a bit of a red flag, because just parroting the words sorry and remorse
don't actually mean that you are sorry or remorseful. It's more convincing for me when offenders are talking
about how they feel, what kind of physical emotions they're feeling. I would like to believe that he was sincere,
but I don't think he was. I think he was going through the motions of saying it.
I don't think it was accurate. I don't think it was believable. NARRATOR: In May 2014, the results of the second trial
was the same as the first. Richard Roszkowski was sentenced to death, but because Connecticut had abolished the death penalty
in 2012, his sentence was eventually changed to life without the possibility of release
at a third trial in 2018. I was just relieved and I'm glad that he'll never ever see the light of day, and he
can't harm anybody else ever. He's damaged and changed a lot of lives with what he did.
And that other family has to live without their granddaughter, and they lost their daughter.
We have to live without my brother. My niece and nephew lost their dad, but for that other family, that mother
lost her daughter and her granddaughter, you know? It's horrible, absolutely horrible.
NARRATOR: We may never know the real reason why Richard Roszkowski decided to kill three people in September 2006,
but there seems to be no doubt that it was driven by his obsession with Holly Flannery.
DANIEL TEPFER: There's always been questions about what the relationship was. There'll always be questions.
I mean, people will never really understand what it was that attracted her to Richard Roszkowski.
I mean, that's one of those things that will never be answered. I don't think we will ever know the true nature
of the relationship between Holly and Roszkowski, because Holly has been silenced.
She's never going to be able to tell her side of the story, and anything that Roszkowski says,
we really have to take with a pinch of salt. And very often in these cases, we look at the victim's behavior.
What did they do to provoke their offender? Did they do anything to encourage him?
And I'd say, no. The only person responsible for these murders is Roszkowski, and that's what we need to remember.
NARRATOR: Roszkowski's infatuation with Holly led not only to her death and the death
of her daughter, but also a man who'd never clapped eyes on either of them until just seconds
before he was executed right outside his home on Seaview Avenue. [MUSIC PLAYING]
EILEEN POTKAY: Tommy should be remembered for, number one, being a hard worker, number two, being the best dad ever.
He adored his children. And number three, he was the best uncle to all the nieces and nephews he had.
They all adored him. And he's loved, and he's missed. WOMAN (ON VIDEO): Who's that Ray Ray?
What's his name? Uncle Tommy. His grandkids, my kids ask about him all the time,
and they always say they would have loved to meet him and sad that they will never get to meet up.
At least, I had him for a little bit. I had him for a little while. [MUSIC PLAYING]
NARRATOR: Richard Roszkowski will never be able to ruin any other lives. The dangerous killer will remain behind bars
for the rest of his days. My experience, listening and seeing Roszkowski, he's one person that can never be rehabilitated.
He is just one of those rare individuals that's just so bad that he should never be able to walk where
the community is ever again. NARRATOR: Roszkowski was completely fixated on Holly Flannery, and whatever their relationship,
nothing could justify his actions. To kill the woman he obsessed over, her 9-year-old daughter, and an uninvolved father of two
in a bloody public execution undoubtedly makes Richard Roszkowski one of the world's most evil killers.
[MUSIC PLAYING]

Richard Roszkowski gunned down three people in Connecticut in 2006, including a nine-year-old.

An in-depth look at the lives and crimes of some of the world's most evil killers, including Jeffrey Dahmer, Ted Bundy, Richard Ramirez, Cary Stayner, Leonard Lake, Dorothea Puente and more.

Brief Summary

Richard Roszkowski murdered Kylie and Holly Flannery, and Tommy Gaudet in a violent outburst fueled by obsession and drug abuse.

Key points

The Tragic Murders in Bridgeport. On September 7, 2006, three people were murdered in Bridgeport, Connecticut, including nine-year-old Kylie Flannery.
Kylie Flannery's Last Moments. Kylie was chased and shot by Roszkowski after witnessing her mother's murder.
Richard Roszkowski's Obsession. Roszkowski's fixation on Holly Flannery led to a tragic series of events culminating in murder.
Witness Accounts of the Shooting. Witnesses describe the chaos and horror of the shooting on Seaview Avenue.
Roszkowski's Trial and Sentencing. Richard Roszkowski is sentenced to death for the murders, but legal technicalities complicate justice.
The Impact on the Community. The murders left a lasting scar on the local community, altering their sense of safety.

Episode highlights

Episode quotes

In the blink of an eye, things can change.

MARGARET KELLEY on the suddenness of tragedy.

3:39WatchAug 27, 2021

Tension

85/ 100High tension

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