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World's Most Evil Killers S05E09 Richard Roszkowski
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00:01On the 7th of September, 2006,
00:04three people were gunned down on a street
00:07in the city of Bridgeport in Connecticut.
00:10The youngest victim, 9-year-old Kylie Flannery,
00:14had been chased down by the lone gunman
00:16and executed at close range.
00:20All of this unfolded in a matter of minutes,
00:23so for anybody witnessing this,
00:25it must have been like watching a scene from a movie play out,
00:28but knowing that it's all too real at the same time.
00:32The killer was 41-year-old Richard Roszkowski,
00:35whose infatuation with Kylie's mother, Holly Flannery,
00:39had come to a head in the most tragic of circumstances.
00:44Even though Holly Flannery was clearly in some fear
00:49of Richard Roszkowski, I don't think for one moment
00:52she could have imagined that would effectively mean
00:55the end of her life and her daughters.
00:57Roszkowski was eventually sentenced to death for killing Kylie
01:01and given life sentences for the murders of her mother, Holly,
01:05and tree surgeon Tommy Gordet,
01:08a man with no connection to the Flannery's.
01:13Roszkowski, he's absolutely evil.
01:15I hate him, and I'm glad that I never have to be
01:19in the same room ever again with him.
01:21Richard Roszkowski had emerged as one of the world's most evil killers.
01:47In May 2009, 44-year-old Richard Roszkowski was sentenced to death
01:54for the murder of three people in a short yet bloody killing spree two and a half years previously.
02:01His youngest victim, Kylie Flannery, was just nine years old.
02:07The twisted killer had become fixated with Kylie's mother, Holly.
02:12It was an obsession that led to tragedy, which played out just after 9am on a quiet sunny morning in
02:20Connecticut.
02:21Local news reporter Daniel Tepfer was one of the first journalists at the scene.
02:29It's a case I'll never forget.
02:31I actually was on my way to work that morning when I got a call to get over to Seaview
02:38Avenue.
02:39And I got there. The police were still there.
02:42They were still interviewing witnesses.
02:44And I started talking to some of the witnesses there.
02:47And I was just appalled at what they were telling me had occurred.
02:53And these are things that will stay with me forever.
02:58At his trial, Roszkowski claimed to be insane
03:02and in a drug-induced haze during the killing spree.
03:07The prosecution team of C. Robert Satie Jr. and Margaret E. Kelly
03:12helped put him behind bars.
03:15I've been doing this for a long period of time, actually 40 years.
03:18What was especially difficult in this case was the fact that
03:23he executed Kylie and the manner in which he executed her.
03:26Shooting her once until she fell and then walking up to her
03:29and giving her the coup de grace, killing her.
03:33It opens your eyes to the fact that in the blink of an eye, things can change.
03:38And I remember it being a beautiful day.
03:40And here's a young girl going to school with her mother.
03:44Next thing you know, there are three people dead.
03:46And I'm sure that for the people that were in the area at the time
03:49and what they may have seen or heard or witnessed,
03:52it's just how things can tragically change in just a split second.
03:59During a second trial in 2014,
04:03Roszkowski would show a remorseful side,
04:05but behind the facade lay a deadly killer.
04:09He had been sent to the state's maximum security mental hospital sometime after his arrest.
04:16And the head of the hospital, who's dealt with the worst of the worst,
04:21called the judge and said,
04:22could you please take him out here?
04:24We can't handle him.
04:26He's too dangerous for us.
04:29That might give you an idea of the kind of person that Richard Roszkowski is.
04:34Cold-blooded, no moral compass, no conscience.
04:38This killer's story begins in January 1965.
04:44All we know about Richard Roszkowski's background
04:48is what he told the authorities after his arrest.
04:52Roszkowski was born in the US
04:54and the information about his background is quite patchy
04:58and we're quite reliant on the things that he's said about it.
05:01So we do have to take it with a bit of a pinch of salt.
05:04But one of the things that he says
05:06is that his father didn't really bother with him.
05:09He felt that his father was quite distant.
05:11From what I remember, not a good student in school,
05:14got involved in drugs early on, was rarely in school later on,
05:19and used to get in trouble, little things,
05:22thefts and vandalism and that kind of thing.
05:26At a very young age,
05:28Roszkowski and his family visited his mother's homeland, Poland,
05:33which, he says, is where his troubles with substance abuse began.
05:38Roszkowski claims that he first tasted alcohol
05:41when he was around five or six years old
05:43and then, when he was ten,
05:45he started misusing substances like marijuana and glue sniffing
05:49and that then progressed on to other things.
05:52Glue sniffing leads to cannabis.
05:54Cannabis leads to cocaine.
05:56Cocaine leads to heroin.
05:58That all leads to a drug problem.
06:00And we're now still only a teenager.
06:03Roszkowski was small in stature,
06:06something that led to him being picked on during his formative years.
06:12Roszkowski claims that his family moved to a new area during his childhood,
06:17and this area was quite deprived, it was quite poverty-stricken,
06:21and it was an area where there was quite a lot of criminal activity going on.
06:25And he claims that he was bullied by the local children in the area,
06:30and then, later on, the people who had bullied him
06:33forced him to join some kind of gang.
06:36So, again, we've got all of these external factors
06:39that are compelling me to behave in a particular way.
06:42Life didn't get any easier for Roszkowski.
06:45He struggled with his drug addiction
06:47and couldn't hold down a regular job.
06:51Roszkowski lived quite a transient life as an adult.
06:54He flitted from job to job.
06:57If you think of the impact on that,
06:59Roszkowski doesn't have this consistent group of people around him,
07:03either colleagues or neighbors,
07:04who act as a bit of an informal check on our behavior.
07:08So, he is off the radar in many senses of the term.
07:14Roszkowski's mother had a house on Trojan Drive
07:17in Bridgeport, Connecticut,
07:18and her son would, sporadically, live with her.
07:22During this time,
07:24he got to know another resident on the street, Holly Flannery.
07:30She got to know Roszkowski's mother quite well
07:33and spent quite a lot of time at her house.
07:36And she gets to know Roszkowski through his mother.
07:39And I think because of the kind of person Holly was,
07:42I think she probably showed him some kindness
07:44and some empathy and some compassion.
07:47Holly Flannery lived on Trojan Drive
07:50with her husband and her daughter, Kylie.
07:53But according to witness testimony from the case,
07:57Holly and Roszkowski became close in the early 2000s.
08:01On the surface, Holly seemed to be a really wonderful person,
08:07a good mother, a great wife.
08:09She did everything that you would think
08:11as a normal mother and a housewife would do.
08:15But below the surface, there was something dark there.
08:18There was something that would cause her
08:20to be attracted to Richard Roszkowski.
08:23By 2004, Roszkowski was serving three years in prison for burglary.
08:30Court documents show that Holly would visit
08:32and speak with him on the phone.
08:35Holly did correspond with Roszkowski in prison,
08:39and I think this came from a place of kindness
08:41and a place of concern.
08:43I think she believed he was somebody
08:45who'd had several disadvantages in life
08:47and she was acting out of friendship to him.
08:50But in terms of the way he interpreted her kindness,
08:54he became fixated with her.
08:56He became obsessed with her.
08:58And it didn't take long before Holly started to become
09:01actually quite fearful of this man.
09:04In a letter Holly wrote to a friend in January 2004,
09:09she stated that she'd spoken to Roszkowski over the phone
09:13while he was still in prison.
09:15She said that she'd been threatened by him
09:18and was told she was going to go off a cliff.
09:21Chillingly, she added,
09:23if I should turn up dead, tell Kylie I loved her.
09:29When Roszkowski is released from prison in 2005,
09:33he moves in with his elderly mother.
09:35So he is in Holly's daily life.
09:38She sees him day in, day out going about her business.
09:42And I think this is the point at which his fixation
09:45and obsession with her intensifies,
09:48and some of his behavior towards her starts
09:50to be quite concerning.
09:52It was obvious at some point that she realized
09:55that he was completely out of control,
09:57that she had no longer could control him,
10:00and he had become a threat not only to her,
10:03but her daughter, who she worried much more about.
10:06In case files, Holly's friend stated
10:09that she appeared more anxious
10:11and was afraid of her obsessive neighbor.
10:14At one point, Roszkowski broke into Holly's house
10:18and threatened her with a gun.
10:21I doubt very much whether she encouraged him,
10:23but like all stalkers, they don't pay attention to reason.
10:27They act irrationally.
10:30And no one could demonstrate that more accurately than Roszkowski.
10:35There was one particular incident in July 2006
10:39where Holly said that Roszkowski had pinned her down
10:41and shaved some of her hair off, and he said to her
10:45that he wanted to basically mess up her hair
10:47so no other man would want her.
10:50So at this point in time, his behavior
10:52has crossed the line to physical violence.
10:56He may have been following her before.
10:58He may have been spying on her,
10:59but now he's actually physically harming her.
11:02So he thinks that Holly is his possession.
11:07He thinks that he owns her,
11:09and this is a really dangerous place to be.
11:11Holly Flannery was worried about her and her daughter's safety.
11:17Her infatuated neighbor was ruining her life.
11:21Something was simmering in the mind of Richard Roszkowski,
11:25and by September 2006, it was ready to boil over.
11:40In September 2006, Richard Roszkowski had grown completely obsessed
11:46with his former neighbor, 39-year-old Holly Flannery.
11:51The ex-prisoner and ne'er-do-well was known to the authorities,
11:55but there appeared to be no reason for concern.
12:00He had a number of arrests for drugs or thefts.
12:05He was flying below the radar.
12:07He was the kind of person that you wouldn't even generally give notice to.
12:12He was just someone in the crowd, I guess.
12:16Roszkowski's mother had moved away from Trojan Drive,
12:19and the 41-year-old was now living a transient life
12:24around Bridgeport, Connecticut.
12:26He'd previously been staying in lodgings on nearby Seaview Avenue.
12:31He was living in this rooming house with some other individuals.
12:35There was some testimony during the trials from one of the individuals
12:39that there was drug use going on.
12:42Not all of the tenants at the house on Seaview Avenue were criminals.
12:47Just before Roszkowski had been asked to leave by the landlord,
12:50he'd crossed paths with a 38-year-old tree surgeon named Tommy Gordett.
12:56He'd been living in this rooming house on Seaview Avenue
12:59with other people who had been working at the landscaping company.
13:03He had been separated from his family
13:04and was hoping to turn his life around and get back to them.
13:08So their paths had crossed and they knew of each other.
13:12But I think in the brief time that they had interacted,
13:15Tommy had plot that Roszkowski was not a nice individual.
13:19He had noticed that he was unpredictable
13:22and he was the kind of person to give a wide berth to.
13:27Tommy Gordett had two children who meant the world to him,
13:31which his sister Eileen Podkay testifies to.
13:36Oh, my God.
13:37You know what? I'm actually getting goosebumps just thinking about it.
13:40When my niece was born,
13:42it was probably one of the most wonderful days of his life
13:45to have a baby girl, and he was hands-on.
13:48He changed her diaper, he fed her, he burped her.
13:50Um, he went shopping for her clothes.
13:54When he became a father, he was an amazing dad to Natasha.
13:58And it was many years later that he had a son.
14:01So Natasha was alone for many years with mommy and daddy.
14:04But my brother was a very hands-on dad and he adored her.
14:08In September 2006, Thomas Junior was 10 and Natasha was 14.
14:16I remember going in his cherry picker.
14:18He was a tree man and he worked for a tree company
14:22and he used to have this big truck with, like the firemen have,
14:26like the big bucket on top.
14:27And I remember going in there and, you know,
14:30feeling like I was on top of the world.
14:32My dad was a great dad.
14:34He made sure that we were always having the best time as possible.
14:38I think him growing up, he didn't have the best father figure.
14:42So he definitely wanted to make sure that his children had,
14:45you know, so much better than what he had.
14:49The last time I spoke to my dad, I was in the driveway hanging out
14:53and he stopped by and said hello.
14:54And, uh, that was the last time I saw him.
14:58Tommy Gordette got up for work on the 7th of September 2006,
15:03but he never made it that far.
15:05At some point during the morning, Tommy and Richard Roszkowski
15:10had a heated exchange over the phone.
15:14Roszkowski phones Tommy and basically accuses him
15:17of having a relationship with Holly.
15:20And Tommy just thinks that this guy has lost it.
15:24He remembers Roszkowski's behavior and just thought,
15:27well, this is just him kicking off again.
15:29Three miles across town on Trojan Drive,
15:32Holly Flannery was getting her 9-year-old daughter, Kylie,
15:37ready for the first day at her new school.
15:40According to testimony at trial,
15:42it would start as a very normal morning.
15:45Holly had gotten Kylie up to get ready to go to-to-to Thomas Hooker's school.
15:50But the 9-year-old would never make it to school.
15:54Holly and Kylie's 41-year-old former neighbor had finally snapped.
15:59After months of intimidation,
16:02Richard Roszkowski was about to put his deadly threats into practice.
16:07Roszkowski went into a rage.
16:10A rage that most people certainly wouldn't be able to understand,
16:15and I don't understand.
16:16But he somehow imagined that Holly was cheating on him.
16:21She had broken off their relationship,
16:23and he was determined to confront the man he believed she was cheating with.
16:30Somewhere in Roszkowski's addled mind,
16:34he believed that Holly and Tommy Gordette,
16:37who were strangers to one another, were in a relationship.
16:41It has never been established under what circumstances
16:44the trio traveled to Seaview Avenue,
16:47although Holly's car was eventually recovered from the scene.
16:51But just after 9 a.m., Roszkowski, Holly Flannery,
16:56and her daughter Kylie arrived at the boarding house.
17:01Now, in terms of Roszkowski's thinking,
17:03he was like a missile at this point.
17:06Here is a man who is very fixed and very rigid in his thinking.
17:09He has decided that he's going to kill Tommy on this day,
17:13and that is exactly what he follows through.
17:16He was just standing outside the house.
17:18He was just simply just standing there outside this rooming house.
17:23When Roszkowski decided, for whatever reason,
17:27was going through his head,
17:28that Gordette must be the man that she was cheating with,
17:31even though they had never even met.
17:34One thing we can be sure of is,
17:36at some point, Richard Roszkowski pulled out a gun.
17:40Gordette yelled at him, like, what is going on here?
17:43Hey, what's going on?
17:44And was neatly shot in the head.
17:47But once Gordette is dead,
17:50it's as if the lock is taken off Roszkowski's self-control.
17:54And he grabs Holly Flannery in a headlock on the street,
17:59in front of her daughter Kylie,
18:01puts his arm round Holly's head.
18:04And Holly is shouting, screaming.
18:08She started screaming,
18:09not in front of my daughter, not in front of my daughter.
18:12He then shot her once in the head.
18:15She falls to the ground.
18:18And then poor Kylie just doesn't know what on earth is going on.
18:21And trying to make sense of it, she runs for her life.
18:25He then runs after her, catches up with her,
18:29shoots her in the back, causing her to fall down
18:31on the sidewalk on her back.
18:34She's face up, screaming, crying.
18:37He then walks and stands right over her
18:39and fires into her face.
18:44In less than three minutes,
18:46Tommy Gordette and Holly Flannery had been shot dead.
18:50And Kylie Flannery was fighting for her life.
18:53The nine-year-old,
18:55who'd meant to be starting a new school that morning,
18:58had been chased along a suburban street
19:00and shot three times at close range by Richard Roszkowski.
19:06So Kylie is a nine-year-old girl.
19:09She's just seen her mother shot dead in front of her.
19:13She's seen her mother's killer kill somebody else.
19:16So I think it's sheer terror in terms
19:19of what's going through her mind.
19:21It's very difficult to process that amount of trauma
19:24and work out what on earth is going on.
19:26So her immediate reaction is to just get away, get out of there.
19:31The thought of that little girl, Kylie, running down the street,
19:36her flip-flops flying off as she ran, scared to death,
19:41and then to be shot and laying on the sidewalk face up,
19:46when Roszkowski stood over her and fired the final shots.
19:51I can't even imagine it had happened.
19:55Paramedics rushed Kylie to hospital,
19:58but her injuries were too severe.
20:00Despite efforts by doctors to resuscitate the nine-year-old schoolgirl,
20:05they couldn't save her life.
20:08There could be no excuse for this,
20:10to take the life of a nine-year-old child lying at your feet,
20:13whom you've shot in the back,
20:14and you decide to execute her effectively
20:16by shooting her twice in the head.
20:19That is a profoundly, profoundly wicked act,
20:24which I think does justify the use of the word evil.
20:29Three people were now dead at the hands of Richard Roszkowski,
20:33and the drug-addicted killer was on the run.
20:37His obsession with his 39-year-old former neighbour had led to tragedy.
20:42Let there be no doubt that Roszkowski was erratic.
20:48Let there be no doubt that he'd always lived on the edge of society,
20:54and that he consoled himself with drugs and crime.
20:58The tragedy of this entire case is his fixation on Holly Flannery,
21:03because without that, these killings would not have happened.
21:07He decides on a course of action,
21:09and he literally just goes and carries it out.
21:11So at any time that morning, on the way over to the boarding house,
21:16in between killing Tommy and Holly, in between killing Holly and Kylie,
21:20he could have decided to stop.
21:22He could have decided not to kill anybody else,
21:25but that was never going to happen, because he had a plan,
21:27and he was going to follow it through.
21:30Detectives arrived at a scene of carnage.
21:33A beautiful, sunny morning had been darkened by a killer
21:37who remained unaccounted for.
21:39Police had no idea who it was,
21:42and no idea if he was going to strike again.
21:46They needed to find Richard Roszkowski,
21:49and they needed to find him fast.
22:00On the 7th of September 2006,
22:0541-year-old Richard Roszkowski had shot three people to death
22:09in broad daylight in Bridgeport, Connecticut.
22:13Tommy Gaudet and Holly Flannery were killed first,
22:17before Roszkowski chased Holly's nine-year-old daughter Kylie
22:21down the street and shot her at point-blank range.
22:25He'd then taken flight.
22:29He doesn't run down the street.
22:30He runs through gardens, jumping over fences
22:32in an effort to escape, because it is 9 o'clock in the morning,
22:37broad daylight, plenty of people about,
22:40and he's committed three ruthless killings
22:44in a matter of moments in plain sight.
22:47This is not a man-killing in private.
22:50This is a man-killing in full public view.
22:54Roszkowski flees on foot,
22:56taking clothing from clothing lines on the way,
22:58so that he can change his clothes and make it look like
23:02he's somebody else.
23:03So he's got the presence of mind to do that.
23:06He also pulls over a motorist and offers them some gas money
23:11to give him a lift to his mother's house.
23:14While Roszkowski made his escape
23:16in an unknowing stranger's vehicle,
23:18detectives were already onto him.
23:21The roommate of Tom Gaudet, who came out shortly after the shooting,
23:25gave the name of Richard Roszkowski,
23:27and he gave the police the location of his mother's residence in Trumbull.
23:32Roszkowski would not remain a fugitive for very long.
23:36He was arrested in the town of Trumbull
23:39with the assistance of Trumbull police officials
23:42who had set up at his mother's residence,
23:46what just happened to be at the dead end of a street,
23:49so they were able to set up a perimeter.
23:51Mr. Roszkowski just appeared to have no effect and emotion
23:55at that particular time.
23:57Across town, stunned journalists had started arriving
24:01at the blooded sidewalks of Seaview Avenue.
24:06When I arrived at the scene, it appeared that there was pandemonium.
24:09People were all over the place.
24:11The police had blocked off most of the streets in the neighbourhood.
24:14They were out questioning people.
24:17I came upon a man sitting in a pickup truck.
24:20He was a landscaper, and he was just sitting there,
24:23slumped over the steering wheel of his truck,
24:28obviously in distress.
24:30So I went over to ask him, you know, what's going on?
24:33Well, as it turned out, he had been driving down the street
24:36on Seaview Avenue and had seen it,
24:38had seen the little girl getting shot,
24:39and it was just so upsetting to him
24:41that he had to pull over, he couldn't drive anymore.
24:44I then went and talked to some other witnesses,
24:48all had similar accounts,
24:50and all who were visibly distressed.
24:53It's just something that it's very hard to comprehend.
24:56The junction of Seaview Avenue and Boston Avenue
25:01is a busy intersection during rush hour,
25:04and many passing motorists had witnessed the very public murders.
25:10One woman recalled hearing Holly Flannery scream,
25:14not in front of my daughter.
25:15You know, she remembers hearing that,
25:17but didn't really see that much.
25:19I mean, it was just everybody had little bits and pieces
25:21of things that they had seen or they had heard,
25:25and you just had to kind of try and put it together like a puzzle.
25:28Many of the witnesses described how calm
25:32Roszkowski appeared to be during the shooting.
25:35This wasn't somebody who was losing it,
25:38who was going mad, who was on a rampage,
25:41and it's very tempting to interpret his behavior in this way
25:44because of how close together these murders were,
25:47but I think he knew exactly what he was doing,
25:50and if you listen to the witnesses describe it,
25:53they talk about him walking and seemingly being unaffected
25:57by what he'd just done.
25:59The murder of three people, one of them a child,
26:03had completely shaken the community,
26:06especially the people who turned up to help.
26:10It was testified to that the ambulance driver and the medic
26:13was impacted very deeply because he had a child,
26:17and it may well have been a daughter about the same age of Kylie.
26:21I do know, in talking to the law enforcement officials
26:24that were there, it impacted all of them deeply.
26:28I think the impact on the local community would have been immense.
26:32This is not the kind of place where multiple murder happens.
26:36People would have just been going about their daily business,
26:39going to buy a paper, taking the kids to school,
26:41getting their morning coffee, and in front of them,
26:44this scene of carnage emerges.
26:46So I think it has left a scar on the community.
26:50In terms of the feeling of safety and security
26:53in your own street, in your own neighborhood,
26:56and the fact that people like this, they walk among us.
27:00They often don't look like monsters,
27:01so it does make us question everybody around us.
27:05As investigators at the scene began to identify the victims,
27:10they reached out to the family of Tommy Gaudet.
27:14I got the phone call, and I was driving in the car,
27:16and I pulled over, and they're telling me that my brother
27:20has been killed and that there was a woman and a child with it also,
27:23and I just couldn't wrap my head around the fact that,
27:26how is this all connected?
27:28And she just kept repeating it to me that, you know,
27:30we're trying to put the pieces of this together,
27:32and that my brother had been leaving for work
27:34and was gunned down when he exited his door.
27:36That's how I found out.
27:38I remember waking up to my mom on the phone,
27:42talking really loud, saying, you know,
27:44what are you talking about?
27:45This can't be happening.
27:47Let me walk outside.
27:48Thomas is sleeping, talking about me.
27:50And I was like, what's going on?
27:52So me, as a curious 10-year-old,
27:54I decided to turn on the news, and I saw, you know,
27:57the helicopter scene of the scene.
27:59You know, all they said was a, you know,
28:04three people have been killed,
28:06and the aerial view of the house was where my dad lived,
28:10and I had recognized it because I had been there, you know,
28:12just a few weeks prior.
28:13So I stumbled out of bed, went outside,
28:17found my mom and my sister in the driveway crying,
28:19and I was like, what's going on?
28:21I know that my dad walked out of his house
28:24and got ambushed and shot in the head.
28:29And I don't know why.
28:32That's all I know.
28:39It appeared that Richard Roskowski had killed Tommy Gordett
28:44because of misplaced jealousy and paranoia.
28:48There was a lot of different stories and theories
28:51about what happened.
28:52I remember hearing, like, a lot of different lines.
28:54Like, it was a love triangle, a crime of passion,
28:57just a bunch of crap.
29:00A bunch of mishmash stories with no facts
29:03or evidence behind them, but I guess for the views.
29:07Before the day of the murders,
29:08Holly and Tommy had never met one another.
29:11They were not known to each other in any capacity whatsoever.
29:14And the only place that they had come together
29:16was in Roskowski's imagination.
29:18He had become so fixated on Holly, so obsessed with her,
29:23that he would sit and ruminate and think
29:26and make up scenarios in his head
29:29that he would convince himself were real.
29:45The date is September 7th, 2006.
29:48Time is 12.05.
29:51Okay, Mr. Rogowski, are you ready to your rise, correct?
29:54Correct.
29:54Okay, and you declined to talk to us today
29:57about what happened today, right?
29:58I didn't commit no crimes, sir.
30:00Okay.
30:01So that's what I'm saying.
30:01You declined to talk to us about the events of today?
30:04They didn't commit no crimes.
30:05They got nothing to talk about.
30:07Okay.
30:09When Roskowski's name was released to the public,
30:12Thomas Junior, who was just ten at the time,
30:16recognised his father's killer.
30:17When they put his mugshot on the news,
30:21I immediately had a flashback to, you know,
30:24just a couple of months prior for my birthday
30:27when my dad was visiting and came to give me a birthday card
30:30and Richard actually drove him because they were roommates.
30:33So I immediately was like, oh my gosh, Mom,
30:36that's the guy who is dad's roommate
30:39and he gave me 20 bucks for my birthday.
30:43Days after the shootings,
30:45the Gaudette family visited the crime scene
30:48on Seaview Avenue.
30:50There were a lot of police officers, of course,
30:52a lot of bystanders, a lot of balloons,
30:55a lot of teddy bears.
30:56I didn't know if those were for Holly and my dad
30:59or if they were for Holly's daughter.
31:02He killed a nine-year-old little girl.
31:04She was a baby.
31:05My son is ten.
31:06She was nine years old.
31:08I mean, not that it justifies my father
31:11or that Holly's death or anything like that
31:14or it minimizes it, but to kill,
31:16to empty the clip in a little girl
31:19while she's running from you, that's like beyond evil.
31:22I know this for 100% certain,
31:25that if my brother had had the opportunity that day
31:28to protect that little girl and save her life,
31:30he would have.
31:31He loved children.
31:35Rostkowski told detectives that he'd been gorging himself
31:39on drugs in the days and hours leading up to the murders,
31:42and he continued to claim to have no memory of the incident.
31:48To my understanding, from what I hear and from what I know,
31:52he was doing crack and heroin and he was on a long drug binge
31:57that had been going on for days, a lot of drugs.
32:00We're talking Xanax, marijuana, alcohol, heroin, crack.
32:04We're talking a lot of drugs in his system.
32:07As well as his out-of-control drug addiction,
32:10detectives discovered Rostkowski's motive behind the murders.
32:15During the police investigation,
32:16they learn of Rostkowski's rather transient, chaotic lifestyle.
32:22They learn of his previous stints in prison and his drug use.
32:27They also come to learn about Holly's experience
32:30being victimized by Rostkowski.
32:33So the picture starts to emerge of a man
32:36who feels entitled to behave in whatever way he wants.
32:40He's very fixated. He's very rigid in his thinking.
32:43And he is self-obsessed. He is me, myself, and I.
32:47He has very little concern for other people.
32:50Although it appeared to be an open and shut case
32:53against the 41-year-old,
32:55authorities soon discovered that Rostkowski had other ideas.
33:00The deranged killer wasn't going down without a fight,
33:04and at his upcoming trial,
33:06he was going to declare that he was insane.
33:19In May 2009, Richard Rostkowski was on trial
33:23at the Superior Court in Bridgeport, Connecticut.
33:27The 44-year-old was charged with murdering Holly Flannery,
33:31her 9-year-old daughter Kylie,
33:34and tree surgeon Tommy Gaudet in September 2006.
33:39Tommy's family were in attendance throughout the hearing.
33:45I just remember seeing him and, you know, asking my mom, like,
33:49can he come out from behind there?
33:50Can, you know, he get us?
33:53And, you know, of course, that's a fear.
33:55This person just killed your dad.
33:56Can they come and kill you next?
33:58There were times where he was literally feet away from me,
34:03and that, you know, that thought comes over you like,
34:06wow, I can, maybe I can get him,
34:08and it's almost like you want to attack him,
34:10and it brings up something inside of you
34:13because you're just thinking he's so close to you,
34:15but it's uncomfortable to be that close to a killer,
34:18a killer that could take two adults
34:19and a child's life within three minutes.
34:22Three minutes, they're all dead.
34:24Rostkowski claimed to have no recollection of the murders
34:28and therefore was not in control of his actions.
34:32The defense tries to claim that Rostkowski is insane,
34:36and by implication, he's not responsible for his actions.
34:41And Rostkowski does play up to this,
34:44so he exhibits some signs of shaking and stuttering in his speech
34:50and trying to appear in a very stereotypical way
34:53to be somebody who is insane.
34:56As well as a claim of insanity,
34:59Rostkowski stated that he'd been on a drug binge
35:02that lasted for days in the lead-up to the killings.
35:06Supervisory Assistant State's Attorney C. Robert Satie Jr.
35:11led the prosecution.
35:13There was a substantial defense that was put on.
35:16It took two different forms.
35:17One was a claim of intoxication,
35:19and the intoxication went to the fact that Mr. Rostkowski,
35:23if the jury determined that he was intoxicated,
35:26we had to disprove that
35:28and show that his intent was not going to be mitigated
35:31or, actually, if he was intoxicated,
35:33it was an absolute defense of the crime.
35:34So I do recall that there was an intoxication claim being made,
35:38and they put a lot of witnesses on concerning that.
35:41There was also a challenge as to the mental status of Mr. Rostkowski.
35:47He was basically trying to say,
35:48this is not my fault, you know,
35:50poor me, look at me, I'm suffering from a terrible condition.
35:53But it was very clear in terms of his behavior around the offenses
35:58that he did know what he was doing.
36:00He had a presence of mind.
36:02He was constantly making decisions and making choices.
36:05Had he been legally insane,
36:08had he been suffering psychosis or something like that,
36:11driving him to behave in a particular way,
36:13he would not have been anywhere near as organized as he was.
36:18Many of the witness statements from the day
36:21painted a very different picture,
36:23that Rostkowski was calm and in control of his actions.
36:28Where he killed them,
36:30there was a light and there was a row of cars.
36:32So there were people who literally looked in their mirror
36:35and saw these people get shot and killed and murdered
36:38through the rear view that were testifying that day.
36:41It was tough testimony, no question about it.
36:44It was tough for everyone in the courtroom to hear.
36:47I'm sure it was tough for many of the witnesses to testify about.
36:51Some of them cried.
36:54Looked over at the jury, some of them were crying.
36:57It was obviously something that they had never heard before,
37:00maybe never even imagined before.
37:02But now, on top of it, they would have to hear
37:04to decide someone's guilt or innocence.
37:08Ultimately, Rostkowski's plea of insanity fell on deaf ears.
37:13I think the jury needed to understand
37:16that Mr. Rostkowski was responsible for his actions
37:20and knew what he was doing when those three people were executed.
37:24We had argued that it was an extreme cruel activity
37:29that occurred in the killing of her
37:32that I suggest led to the finding of the jury
37:34that Mr. Rostkowski deserved the death penalty.
37:36The verdict was guilty on the capital felony,
37:39and he was subsequently sentenced to death.
37:44But in an agonizing twist for the victim's families,
37:49a legal technicality meant the judge was forced
37:52to overturn the jury's decision.
37:54Rostkowski's conviction was upheld,
37:57but a second sentencing trial would have to take place in the future.
38:03In December 2011, Rostkowski was interviewed in prison
38:08by psychiatrist Dr. Howard Zanana.
38:11He still claimed to have no memory of the events.
38:16I was up three days hallucinating out of my mind,
38:19and I don't remember from point A to point B,
38:22and when I woke up, three people said,
38:24how do you want me to explain something like that to anybody,
38:27to a judge, to anybody?
38:30Rostkowski did, however, allude to a reason behind the killing spree.
38:35He claimed to have discovered a letter in his mother's home
38:39on the morning of the 7th of September 2006.
38:43I found a letter on my mother's bureau
38:47that had the address of C.U. Avenue number,
38:52and it was from the person saying,
38:54you're never going to see her again,
38:55because I really love Holly.
38:58I was mad because then I picked up the phone,
39:00and I called him, and then he answered the phone.
39:03And he was who?
39:04That was Tom Gaudette.
39:06Gaudette?
39:07Gaudette.
39:08Gaudette.
39:09And was he one of the victims?
39:11Correct.
39:12And he, like I say, he was, it was him that,
39:17as far as I was concerned, the way it was worded,
39:19it was worded like it was directly from him.
39:21Okay.
39:22You know, when I confronted him about it, he said no,
39:25and then he turned around and changed the story,
39:27and he says, yeah, I wrote the letter, what of it?
39:30The last thing I remember was finding the letter,
39:34making the phone call to Tom,
39:37and then after, like I say, all that whole thing,
39:39I closed the phone, and I did all the drugs, and I blacked out.
39:44Right.
39:44So you don't remember doing any of the killings?
39:48No.
39:48No letter has ever been found by police investigating the murders,
39:54and no link between Tommy Gaudette and Holly Flannery
39:57has ever been established.
40:00Richard Roszkowski's resentencing trial took place in 2014,
40:05and this time he was given the opportunity
40:08to speak to the families of his victims.
40:12All I can say is I'm truly, deeply remorseful for what happened,
40:18and I'm truly, deeply sorry for the pain that I have caused
40:21to you and to all the family members.
40:26I am truly, truly sorry for your pain.
40:29He says, I feel sorry, I feel remorse,
40:32and for me that's a bit of a red flag,
40:35because just parroting the words sorry and remorse
40:39don't actually mean that you are sorry or remorseful.
40:43It's more convincing for me when offenders are talking
40:45about how they feel, what kind of physical emotions
40:48they're feeling.
40:50I would like to believe that he was sincere,
40:53but I don't think he was.
40:54I think he was going through the motions of saying it.
40:57I don't think it was accurate.
40:58I don't think it was believable.
41:00In May 2014, the result of the second trial
41:05was the same as the first.
41:07Richard Roszkowski was sentenced to death.
41:09But because Connecticut had abolished the death penalty in 2012,
41:14his sentence was eventually changed to life
41:17without the possibility of release at a third trial in 2018.
41:23I was just relieved, and I'm glad that he'll never,
41:26ever see the light of day, and he can't harm anybody else, ever.
41:29He's damaged and changed a lot of lives with what he did.
41:33And that other family has to live without their granddaughter,
41:36and they lost their daughter.
41:37We have to live without my brother.
41:39My niece and nephew lost their dad.
41:41But for that other family, that mother lost her daughter
41:44and her granddaughter.
41:46You know, it's horrible.
41:48Absolutely horrible.
41:50We may never know the real reason why Richard Roszkowski
41:54decided to kill three people in September 2006.
41:59But there seems to be no doubt that it was driven
42:02by his obsession with Holly Flannery.
42:07There's always been questions about what the relationship was.
42:11There will always be questions.
42:12I mean, people will never really understand what it was
42:17that attracted her to Richard Roszkowski.
42:20I mean, that's one of those things that will never be answered.
42:23I don't think we will ever know the true nature
42:26of the relationship between Holly and Roszkowski,
42:29because Holly has been silenced.
42:32She's never going to be able to tell her side of the story.
42:34And anything that Roszkowski says,
42:36we really have to take with a pinch of salt.
42:39And very often in these cases, we look at the victim's behavior.
42:42What did they do to provoke the offender?
42:45Did they do anything to encourage him?
42:47And I'd say no.
42:48The only person responsible for these murders is Roszkowski,
42:53and that's what we need to remember.
42:56Roszkowski's infatuation with Holly led not only to her death
43:00and the death of her daughter,
43:02but also a man who'd never clapped eyes on either of them
43:06until just seconds before he was executed
43:09right outside his home on Seaview Avenue.
43:15Tommy should be remembered for, number one, being a hard worker,
43:20number two, being the best dad ever.
43:22He adored his children.
43:24And number three, he was the best uncle
43:26to all the nieces and nephews he had.
43:28They all adored him, and he's loved and he's missed.
43:33Who's that, Ray Ray?
43:34What's his name?
43:36Uncle Tommy.
43:38His grandkids, my kids, ask about him all the time.
43:42And they always say they would have loved to have met him.
43:46It's sad that they won't ever get to meet him.
43:49At least they had him for a little bit.
43:52Had him for a little while.
43:57Richard Roszkowski will never be able to ruin any other lives.
44:02The dangerous killer will remain behind bars for the rest of his days.
44:07My experience listening and seeing Roszkowski is one person that can never be rehabilitated.
44:13He is just one of those rare individuals that's just so bad that he should never be able to walk
44:20where the community is ever again.
44:26Roszkowski was completely fixated on Holly Flannery, and whatever their relationship, nothing could justify his actions.
44:34To kill the woman he obsessed over, her nine-year-old daughter, and an uninvolved father of two, in a
44:41bloody public execution, undoubtedly makes Richard Roszkowski one of the world's most evil killers.
44:52Aspten, mungkin decision.
44:53The happening is from HR DC famous.
44:55We do not ever work.
45:02We don't list these other guards who care about others.
45:03We have someone who enred me about daily visits and others.
45:09And there are people who care about them.
45:09You