Money, Moguls and Murder

Summary

Cold Case Files: "Money, Moguls and Murder"

Introduction

In the "Money, Moguls and Murder" episode of Cold Case Files, host Paula Barros delves into the harrowing story of Debbie Clark, a nurse whose brutal murder in Miami in 1977 remained unsolved for decades. This episode underscores the challenges faced by investigators in cracking cold cases and highlights the pivotal role of advancements in forensic technology in delivering justice long after a crime has been committed.

Background of the Victim

Deborah "Debbie" Clark was a vibrant and ambitious young woman from Utica, New York. At 23 years old, Debbie sought to carve out a new life for herself in the bustling city of Miami, Florida. As Roxanne Clark, Debbie's stepsister, recounts, "Debbie was a typical small city girl that wanted to lead a different life. She was a nurse. She moved to Miami to start a new life" [02:29]. Debbie's pursuit of excitement and success led her to a promising job in the emergency room, where she became a beloved colleague and friend.

The Murder and Initial Investigation

On August 6, 1977, Debbie failed to report for work, sparking concern among her friends and colleagues. Tom Guilfoyle, a patrol officer with the Miami Dade Police, responded to the missing person report. Upon investigating Debbie’s townhouse, he discovered her lifeless body in the bedroom. "This is not a natural death. This is a homicide," Guilfoyle stated upon finding her [04:55]. The scene was meticulously arranged, with no signs of forced entry, suggesting that the perpetrator had either been let in by Debbie or possessed a key.

Debbie’s murder exhibited extreme brutality, including a gunshot wound to her chest and evidence of strangulation and assault. Detectives quickly ruled out robbery as a motive, considering the lack of signs indicating a struggle for valuables. Instead, they surmised that the crime was personal, possibly involving someone close to Debbie.

The Case Goes Cold

Initial suspects included Debbie’s ex-husband, Phil Clark, who had a seemingly amicable divorce, and her new boyfriend, Alan Bregman, a wealthy real estate mogul. Despite thorough investigations, including questioning Phil Clark and scrutinizing Alan’s alibi, no substantial evidence linked them conclusively to the crime. Additionally, Ray Sobel, the maintenance caretaker employed by Alan’s father, emerged as a person of interest due to his access to Debbie’s apartment and loyalty to the Bregman family. However, without concrete physical evidence, Ray's involvement remained speculative [20:10].

The case languished as one of Miami Dade County’s oldest cold cases, with detectives feeling the strain of numerous other violent crimes, including those committed by serial killers like Samuel Little [09:45]. Over time, hope waned, and the investigation stalled, leaving Debbie’s family devastated and without closure.

Renewed Efforts and Advances in Forensics

Decades later, the persistent efforts of retired patrol officer Tom Guilfoyle rekindled hope. Guilfoyle frequently revisited the case, convinced of its solvability long after his retirement. His unwavering determination prompted detectives Denmark and Grossman to reopen the case in March 2015 [24:10]. With advancements in forensic technology, particularly DNA analysis, the investigation gained new momentum.

Investigators focused on a hair found on Debbie’s body, which was preserved as evidence. Realizing its potential, detectives utilized modern DNA testing to extract mitochondrial DNA from the hair sample. "We knew that the hair could have been left by the killer," Detective Grossman explained [25:35]. This development was pivotal, offering a tangible link to the perpetrator after nearly four decades.

Breakthrough and Arrest

Further scrutinizing Alan Bregman’s activities, detectives uncovered discrepancies in his alibi. An Eastern Airlines ticket mutation revealed that Alan had altered his flight dates, placing him in Miami during the time of Debbie’s murder, contrary to his initial claim of being in New York for Coast Guard training [28:41]. This revelation cast significant doubt on Alan’s innocence.

Additionally, a crucial tip from Joe Thompson, a friend of Alan’s, surfaced. Thompson disclosed that Alan had purchased a firearm for Debbie and had taken her gun from her apartment, which was later used in the murder [37:30]. Coupled with the DNA match from the hair sample, which linked Alan directly to the crime scene, the evidence mounted against him became overwhelming.

On August 4, 2016—the 39th anniversary of Debbie’s murder—Alan Bregman was arrested in North Carolina [35:11]. The prosecution faced challenges, including the aging witnesses and the time elapsed since the crime. However, the combination of DNA evidence and circumstantial factors provided a robust case against Alan.

Trial and Conviction

During the trial, the prosecution presented compelling evidence, including the DNA match and testimony regarding Alan’s conflicting statements and suspicious behavior following the murder. Debbie's stepsister, Roxanne Clark, expressed profound relief upon Alan’s conviction: "I know it. I knew it all along." [41:29]. Despite Alan’s steadfast denial of involvement, the jury found him guilty of second-degree murder by a firearm, sentencing him to life in prison [41:18].

The trial highlighted the profound impact of technological advancements in solving cold cases. Investigators emphasized the significance of never giving up on seeking justice, regardless of how much time has passed.

Wrap-Up and Reflections

The resolution of Debbie Clark’s case after 39 years serves as a testament to the relentless pursuit of justice by law enforcement and the vital role of forensic science. Ruthless dedication from individuals like Tom Guilfoyle and breakthroughs in DNA technology bridged the nearly four-decade gap, providing closure to Debbie’s family and affirming that even the coldest cases can be solved with perseverance and innovation.

Debbie’s memory lives on through the heartfelt reflections of her family, who reminisce about her vibrant spirit and the bright future she deserved. As Roxanne Clark poignantly stated, "Debbie was young. She didn't get to do all the exciting things and be everything that she could be. A lot of good memories. [...] She's never forgotten." [42:07].

This episode of Cold Case Files not only recounts a tragic tale of loss and the quest for justice but also inspires hope that no matter how long a case remains unsolved, determination and advancements in investigative techniques can ultimately prevail.

Notable Quotes

• Roxanne Clark on Debbie’s character: "Debbie was a typical small city girl that wanted to lead a different life. She was a nurse. She moved to Miami to start a new life." [02:29]

• Detective Tom Guilfoyle on discovering the body: "Going around with a flashlight in one hand and a gun in the other in a darkened house did get the adrenaline going. It's not a natural death. This is a homicide." [04:55]

• Narrator on the rarity of solving cold cases: "There are over 100,000 cold cases in America. Only about 1% are ever solved. This is one of those rare stories." [02:10]

• Roxanne Clark on receiving the call about Debbie's death: "I couldn't believe it. I couldn't believe it. I just, I was shocked." [04:55]

• Detective Grossman on the DNA breakthrough: "Tell me, tell me. There was a familiar match to that hair." [34:15]

• Tom Guilfoyle on the DNA match: "When I learned that the DNA matched 39 years after the murder, I was extremely, extremely happy, satisfied, almost elated." [35:11]

• Roxanne Clark on the conviction: "I know it. I knew it all along." [41:29]

Conclusion

"Money, Moguls and Murder" exemplifies the essence of Cold Case Files by illustrating the intricate dance between unresolved mysteries and the unyielding pursuit of truth. It highlights how dedication, combined with evolving forensic methodologies, can bring closure to victims' families and uphold the integrity of the justice system.

Transcript

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[Roxanne Clark]

Deborah Clark was my stepsister. She was a kind, gentle, loving soul. She also was so much fun. And she was looking for excitement. So she goes to Miami. That's where it's at. The lights, the glitter, the seventies. She had friends. She got an excellent job. She met, you know, a fantastic guy. The world was hers. And then we get this grand slam phone call.

[Detective]

The brutal way that Debbie was murdered. This was not somebody who came in, shot Debbie and ran out. It couldn't have been her boyfriend.

He was in New York in a love triangle situation. His wife was the one that was being scorned.

Debbie's case was the oldest cold case in Miami Dade County.

[Roxanne Clark]

We succumbed to the idea that nobody was gonna pay the price. We almost gave up hope. And then all of a sudden, there's a knock on the door.

[Narrator]

There are over 100,000 cold cases in America. Only about 1% are ever solved. This is one of those rare stories. It's August 6, 1977. Roxanne Newson lives in Miami, Florida.

[Roxanne Clark]

My sister Debbie was a typical small city girl that wanted to lead a different life. She was a nurse. She moved to Miami to start a new life.

[Narrator]

David Orvalle is a journalist at the Miami Herald.

[David Orvalle]

In the late 70s, Miami was still sort of a freewheeling kind of place. So many people come here from other places who are looking to make a fresh start. And Debbie was sort of a free spirit. She had a lot of ambitions, a lot of dreams.

[Roxanne Clark]

Debbie was supposed to report to work, which she always did. Never missed a shift, never called in. But she never showed up. And her nurse friends there were starting to get worried.

[Tom Guilfoyle]

Her friend said, something's wrong. This is not like Debbie. They called the police. It went out originally as a missing person case. I was on uniform patrol. I was dispatched there in the evening of August 6th.

[Narrator]

The young patrol officer meets 23 year old Debbie Clark's friends outside her home. Tom Guilfoyle is a former patrol officer with the Miami Dade Police.

[Tom Guilfoyle]

It was a very nice neighborhood. Debbie's townhouse was a two story structure. A lot of missing person cases. People just take off and forget to tell their friends, but she's not the kind of person to do something like that. Also, her car was there. So she didn't just go away for the weekend, or if she did, she didn't drive herself. The first thing to do is look for signs of a burglary or a forced entry. All the doors were locked, no windows were broken, no windows were open, no signs of forced entry.

[Narrator]

Guilfoyle spots a large window on the second floor balcony.

[Tom Guilfoyle]

I know how to climb things and it was really my only option. I got to the balcony with the sliding glass door. That's when I saw a human body lying on the bed. So I popped up the sliding glass door and went inside. It was dark, so I used my police flashlight to illuminate the place. The victim was lying on her back on the bed. It was obvious to me that she was deceased. Going around with a flashlight in one hand and a gun in the other in a darkened house did get the adrenaline going. It's not a natural death. This is a homicide.

[Roxanne Clark]

I get the phone call. They found Debbie dead. And she'd been dead, you know, like three days. She had been murdered. And I just, I couldn't believe it. I couldn't believe it. I just, I was shocked. I can't tell you just where your heart is until you hear those words.

[Narrator]

In addition to Roxanne, Debbie leaves behind a stepsister, two siblings, her mother and father, and stepparents.

[Roxanne Clark]

Growing up, Debbie was the best sister.

[Narrator]

Debbie's humble beginnings in Utica, New York motivated her to strive for something better.

[Roxanne Clark]

Debbie, she was a little more adventurous than me. She was braver, and I was a follower.

[Narrator]

At 17, Debbie convinces her younger sister to take a bold and risky trip to sunny California.

[Roxanne Clark]

We got our money together, we packed a suitcase and she said, okay, let's go. The adventure starts. So we stuck our thumbs out and of course it was amazing. But we didn't realize in California you had to be 18 or 21 at that time, really, to do anything. And you had a 16 year old and a 17 year old, you know, wandering the sunset straight. So we ran out of money, so we started to head home. A little while later, I had become pregnant. Debbie went back to school. She had fallen in love with this fella, Phil.

[Narrator]

Debbie enrolls in the nursing program at a local community college.

[Roxanne Clark]

Debbie was very smart and she could do the work.

[Narrator]

Debbie and Phil are married in 1973, and the following year, Debbie earns her nursing degree.

[Roxanne Clark]

Debbie's husband was a construction worker. He was laid back, Grizzly Adams type of guy. And one day Debbie called me and she said, roxanne, I'm at Syracuse Airport with the vehicle. And I said, what are you doing? And she said, well, Phil's become more like a brother to me. I've decided to go to Miami and start a new life. So she goes to Miami, gets a job in the emergency room. Debbie and Phil were still married, but she was ready to move on.

[Tom Guilfoyle]

This was my first homicide. And when it's a violent murder, of course, the stress for everybody goes up. Whoever got in was either let in by Debbie, the victim, or had a key. The air conditioner was set very cold in that townhouse, possibly by the killer, to kind of obscure the time and date of death. But a victim could have stayed in there for a long time.

[Narrator]

Detectives don't believe this was a case of robbery gone wrong. Jonathan Grossman is a cold case detective with the Miami Dade Police.

[Detective]

This was a brutal murder. This was not somebody who came in, stumbled upon somebody, shot them and ran out. This is somebody who shot Debbie and then choked Debbie and beat Debbie. And it was very, very brutal.

[Tom Guilfoyle]

Some of her hair had been pulled out. I saw blood on her face and on her chest. And there was a gunshot wound right in the middle of her chest.

[Detective]

The crime scene itself was isolated to the bedroom, and that's where the victim's body was. One of the things we discovered on the bed was her purse had been empty.

[Narrator]

Debbie's friend tells officers that Debbie kept a gun in the purse found on her bed.

[Tom Guilfoyle]

Then they processed the clothing, the bed sheets. They turned her over. That's when we saw the gun grips.

[Detective]

It's possible that the offender in this case obtained the firearm from her purse and ultimately shot her and in this case, beat her and beat her so bad that the gun grips literally broke off the firearm.

[Tom Guilfoyle]

I was with them when they were processing the body. One of the crime scene technicians spotted a hair on her arm, but it was such A small hair. They took that picture of my hand pointing to the hair.

[Narrator]

The hair is bagged and entered as evidence. As they process the scene, Miami detectives start to wonder whether Debbie's murder is connected to other killings.

[David Orvalle]

In the late 70s, there was a bunch of serial killers running around in Miami dade. We had a guy picking up hitchhikers and leaving their bodies around. A guy by the name of Samuel little ended up being the most prolific serial killer in American history.

[Narrator]

In the months leading up to Debbie's murder, there had been a rash of killings in Miami's Carroll city neighborhood. Those other victims had been gunned down just like Debbie. David denmark is a cold case detective with the Miami Dade police.

[Detective]

The Carroll city serial killer committed several murders in the same place on the same day. He killed the homeowner and family members, walked into the house one after the other, and he took all of them out. The Carroll city serial killer became an interest to us.

[David Orvalle]

Detectives had to explore the possibility that Debbie's murder could have been the work of the serial killer.

[Detective]

The Carroll city serial killer became an interest to us.

[Narrator]

A spree of killings that began in October 1974 is now making news. Just eight days before Debbie Clark's murder, six people were shot and killed in their Carroll city home.

[Detective]

The weapon of choice of the serial killer was a.357 Magnum. We needed to compare the projectile that was found in both cases.

[Narrator]

The autopsy report gives investigators an important clue.

[Detective]

The projectile that was found in Deborah's case was a harrington and Richardson, top break.38 caliber. It did not match with the gun that that serial killer used.

[Narrator]

The Carroll city killer is eliminated as a suspect.

[Detective]

Debbie was murdered on August 4, four days before her body is discovered.

[David Orvalle]

The medical examiner's autopsy revealed that Debbie hadn't just been shot. If it was just a burglar, they might have just shot her, right? Or they wouldn't have had a gun and they would have just beat her. But in this case, it was both. And that kind of indicates a level of intimacy, a level of it being personal between the killer and the decedent.

[Roxanne Clark]

Debbie's mother was very overwhelmed when the detectives told her that she had been murdered. Debbie's father worked in a factory down in Utica. The three to 11 shipped, and back in the 70s, you know, he didn't make a lot of money. Her father flew down to Miami. He wanted to do everything to help bring his daughter's murderer to justice.

[Tom Guilfoyle]

He was interviewed by the detectives, and he said Debbie was married before to a man named Phil Clark. An ex husband is a logical suspect.

[Roxanne Clark]

Phil was quite a bit older than her, and he wasn't very adventurous. I think just becoming that everyday, mundane housewife at 22 just wasn't cutting it for her.

[Narrator]

Debbie's father tells investigators his daughter was seeing someone new.

[Roxanne Clark]

Everybody in the family really liked Alan. He was personable. He was gracious, friendly. He had money. He was a big real estate mogul. His father was very wealthy and well known in Miami area. So he showed Debbie quite the glamorous life.

[Tom Guilfoyle]

We found out the condo that she lived in had been purchased for her by her boyfriend.

[Roxanne Clark]

Allen was fully involved in Debbie's life with her friends. They would go out for dinner as couples. He came up to New York and met her mother and father. They said, we're going to be married.

[Narrator]

But it's not that simple.

[Roxanne Clark]

Debbie and Phil were still married, and Debbie knew that Alan was married, too, because he had a son, and he would bring his son over to Debbie's condo. But they had made a decision that both of them would get divorced and get married. And in fact, when the detectives went into Debbie's condo, her divorce papers were on her nightstand. The official divorce had gone through probably about a week before she was murdered.

[David Orvalle]

Miami Dade police have to try to figure out, could it have been the husband?

[Tom Guilfoyle]

They interviewed, Phil Clark, found out that he was up there in New York state. Apparently, the divorce was friendly. There was no animus between them.

[Narrator]

Phil is off the hook, but the new man in her life, Alan Bregman, isn't.

[Tom Guilfoyle]

They went to talk to her boyfriend and Allen and knocked on his door.

[Narrator]

As homicide investigators, Allen's wife, Honey, answers the door.

[Tom Guilfoyle]

They said, we're here to investigate the homicide of a Deborah Clark. The subject's wife got up and walked out of the room with a very upset look on her face.

[Detective]

Alan Bregman was not truthful to his wife, But I'm pretty sure she saw the big picture of what was going on.

Honey had recently found out about the relationship that Allen was having with Debbie. Was this a murder that occurred because Honey was upset with the other woman? One of the things that they evaluated were who was in Miami on August 4th. We know that Debbie returned home from work and was last seen at work on August 4th in the morning. Allen says at the time, he was in New York at an auxiliary school for the coast guard, and he had an airline ticket that proved that he was in New York at the time that Debbie was murdered. So it couldn't have been Alan. But we knew that Honey was in Miami at the time. The detectives interview Honey several times.

They believe that in a love triangle situation, Honey was the one that was being scorned. Maybe Deborah was killed by Honey Bregman. Honey now becomes a suspect.

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[Roxanne Clark]

Alan was living a double life and his wife found out we knew that.

[Detective]

Honey was in Miami at the time of the murder.

[Narrator]

When police questioned her, Honey points them to someone else.

[Detective]

Honey Bregman mentioned they had a landscaper by the name of Ray Sobel and she also told us that Ray Sobel was the maintenance caretaker of the apartments where Deborah was killed and that he had the key and access to the apartment.

[Narrator]

Ray also was in Miami on August 4, the last day Debbie was seen alive.

[Detective]

We know Ray Sobel was here at the time and we knew that Honey was in Miami at the time.

[Narrator]

But after a few days of scrutiny they realized she's probably not the killer.

[Detective]

Honey had a small son. She had a full time job as a teacher at a local school. She was a smaller petite woman we ruled her out based on some of those things, but we definitely kept Ray Sobel as a suspect. He was employed by Alan's father to go around and collect rent.

Alan Bregman's father was very powerful. He was very wealthy. Ray Sobel was very loyal to Alan Bregman.

Allen and Ray did everything together. He was somebody who knew everything about Allen, including the relationship that Allen had with Debbie.

[David Orvalle]

He's someone that maybe doesn't have a direct motive to want to harm Debbie, but this is someone that works for the Bregmans, that wants to keep working for the Bregmans. It was something they could not discount that he was doing this on behalf of someone else in the Bregman family.

[Detective]

Ray had been contacted by the police, but he was very reluctant to speak.

He lawyered up. Did Ray Sobel know what had happened? Possibly. Did he have an involvement in it? Possibly.

[Narrator]

With no physical evidence, police can't tie Ray to the crime.

[Detective]

But we definitely kept Ray Sobel as a person of interest.

[Roxanne Clark]

After Debbie was murdered, family would get together. We thought about people that could have been suspects in Debbie's murder.

[Detective]

Deborah Clark's family just wanted to know who did this to her.

One of the items that detectives discovered early on was a life insurance policy that Debbie had purchased for herself.

[Narrator]

Debbie bought the policy five months earlier, in April 1977, with a payout of $148,000.

[Detective]

The beneficiary was initially her sisters.

[Roxanne Clark]

Debbie was the older sister to these younger sisters. Debbie loved those kids so much that when she moved to Miami, she got out a life insurance policy, and those two were the beneficiaries. Five weeks before the murder, Alan convinced Debbie, if you put your insurance in my name and something happens to you, I will get the condo and it'll be paid for.

[Detective]

The beneficiary had been changed from a sister to Alan Bregman.

[Roxanne Clark]

Debbie was found murdered on a Saturday, and Alan went and called the life insurance company trying to collect the money on Monday.

[Detective]

So that kind of raised an eyebrow as to Alan making money from Deborah's death.

[Narrator]

Alan's attempt to collect on the insurance policy is odd, since he didn't need the money.

[Detective]

We didn't believe that that was the motive because Alan had money and his dad had money.

[Tom Guilfoyle]

Murders were happening almost literally every day. The homicide bureau was stretched pretty thin back then.

[Detective]

You know, you also had the cocaine cowboys, a lot of drug murders. And so that's one of the challenges that we had. The information wasn't coming in as fast, and so I think it just got to the point where detectives just felt that they didn't have anything else at that time.

[David Orvalle]

1977 was one of those years that stands out for a lot of old timers because that was the first year that it snowed in Miami.

[Narrator]

With no new leads, the case of the murdered nurse goes cold until August 1978, one year after Debbie is murdered.

[Roxanne Clark]

Debbie's father couldn't stay in Miami through the investigation, and he always felt guilty that he didn't do more to help the police find the killer. Frank was never, never the same again. Debbie's father succumbed to the idea that his daughter was gone and nobody was going to pay the price. And that's how he died.

[Tom Guilfoyle]

Not knowing, I could not forget the case. I ended up getting a little more rank. You could talk to the homicide detectives, and I did so a number of times. I even did it after I retired. My belief was that this case was solvable.

[Narrator]

It's now March 17, 2015, in Miami, Florida, 37 years after Debbie Clark is murdered.

[Roxanne Clark]

Tom Guilfoyle kept going up to the cold case file room and said, have you guys ever looked at this again? Because this really bothers me. They got the cold case filed down, and they started going through it, and they're like, my goodness, my goodness, my goodness. And that's when the ball started rolling.

[Detective]

When we started to look at the case file, we realized that this will break this case open. Miami Dade has over 10,000 cold cases, and there's three of us. But there are investigators out there that will break their backs to do the job and sacrifice his own life to bring closure to yours.

We opened up this large box. We were able to identify pictures from the crime scene. And one of the things that we noticed was the passion and the brutal way that Debbie was murdered.

[Narrator]

Investigators wonder if the killer left behind traces of his DNA during his attack.

[Detective]

On Debbie back in 1977. They had no idea what DNA was. We wanted to see what physical evidence we still had in our possession that we can test with current technology.

Today we saw a photograph of a hair on Deborah Clark's arm.

We knew that the hair could have been left by the killer.

There was a specific lab located in Virginia that would crush the hair to obtain mitochondrial DNA. Myself and Detective Grossman flew to Virginia. We wanted to make sure we hand delivered it.

Lab testing is one of those things that could take months in some cases, could take years. It really puts you in a state of, okay, what do we do? And trying to figure out other things that need to be done. In the meantime, as a cold case investigator, One of the things that we do is determine what witnesses are still alive. What we know about Allen is that he ultimately moved to Boca Raton. He raised his son. He didn't really have any other run ins with the law. Alan Bregman's wife, Honey, had already been deceased by that time.

[Narrator]

Honey died 11 years earlier, in 2004. Ray Sobel, Debbie's apartment maintenance man and her boyfriend. Alan's pal, however, is still alive. He agrees to meet with detective Denmark.

[Detective]

Ray Sobel lived in a trailer park in Naples, Florida.

We knew that Ray had interacted with the police back in 1977, 38 years later, his demeanor was a little bit different. He was willing to speak with us.

He let us in the house. He had us sit down, offered us a drink, said, what can I do for you?

Ray expressed to us that he had no involvement in Debbie's death. His relationship with Allen was no longer there, so he was willing to tell us what he knew. One of the things we wanted to know was where were they on August 4th at the time of the murder?

Ray Sobel says Honor Bregman had gone to a coast guard search and rescue school in New York. He had completed Sunday, Monday, Tuesday, Wednesday, and got the phone call that his wife had found out about Deborah Clark.

[Narrator]

Ray tells detectives that Allen returned to Miami from New York on Thursday, the day Debbie was murdered.

[Detective]

Debbie thought she was the number one. Alan says, hey, we gotta cool things down, and we take a break. And Debbie said, why do we need to take a break? You're with me. We think that that's sort of where the aggression took place, which ultimately led to her murder.

[Narrator]

Detectives Denmark and Grossman still need to prove Allen was even in Miami when Debbie was killed.

[Detective]

One of the items that we found in the file was an airline ticket from Eastern airlines.

These were paper tickets, like the. With the scan with the little holes punched out.

We found a group out of Miami international Airport of older flight attendants. They knew every code that was written on that ticket, knew what the change codes meant. Alan changed his airline ticket.

What we discovered was he changed his date of arrival from Sunday to Thursday, and that's when we believe the murder took place.

He's lying. Anytime someone provides you with an alibi as to their whereabouts at a specific time that you can disprove, that's a huge piece of evidence. This is where we started focusing more on Allen.

[Roxanne Clark]

The whole family suspected Alan Bregman. Debbie's mother had a feeling it was Alan Bregman but until it's proven and done, you just suspect.

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[Narrator]

It's now May 1, 2016, 39 years after Debbie Clark is murdered. Now that detectives Denmark and Grossman know that Alan Bregman's alibi is a lie, they again question Debbie's friends.

[Detective]

On August 2nd, Debbie had some friends over for dinner. And this would have been two days before her murder and approximately four days before her body's discovered. We showed them pictures we discovered in the case file. We asked them to look for things that look out of the ordinary.

[Narrator]

Debbie's friends tell detectives something is off.

[Detective]

One of the items that we discovered were photographs of Debbie standing in front of a collage of photographs. The friend remembers that the collage was on her wall prior to her death. But the photographs were removed from the wall by the time the detectives arrived. One of the other things that her friends remember is that Allen's clothing was still present in the closet. This was very important to us because upon discovery of Debbie's body, the clothing had been removed and the photographs had been taken off the wall.

[Narrator]

Investigators believe Alan might have been trying to erase any evidence of his relationship with Debbie.

[Detective]

The investigation into Alan started going very fast.

The circumstantial evidence was 100% in our minds, Alan is guilty. Now we need the physical evidence.

[Narrator]

After two months, analysis on the hair police collected from Debbie's body is finally complete. It could bring detectives one step closer to charging Allen Bregman.

[Detective]

When the report finally came in, Detective Denmark was like, what?

[Roxanne Clark]

What?

[Detective]

Tell me, tell me. There was a familiar match to that hair.

It comes back to Allen or his son or his father. His son was three years old in 1977. So immediately eliminate him. Immediately eliminate the father. Because why would a guy with everything in the world want to go and kill somebody? Because we had probable cause against Alan Bregman, we were able to obtain a search warrant for his DNA.

[Narrator]

The now 75 year old real estate agent meets detectives at his Lawyer's office.

[Detective]

I was looking at his behavior. He played the role of almost like a victim. How dare we investigate him.

We got a phone call saying his DNA matched.

[Tom Guilfoyle]

When I learned that the DNA matched 39 years after the murder, I was extremely, extremely happy, Satisfied, almost elated.

[Detective]

The decision was made to prepare an arrest warrant for Alan Bregman. Upon receiving the information that he moved from Boca Raton to North Carolina, we immediately contacted the local authorities in North Carolina. We told them to please go to his residence right away and to physically arrest him. Cold case arrest.

[David Orvalle]

Nearly 40 years after a south Florida nurse is brutally beaten and shot and.

[Detective]

Killed, her accused killer is now in custody.

[David Orvalle]

75 year old Alan Bregman was arrested.

[Detective]

In connection with the murder of Deborah Clark, who was found inside her home way back in 1970.

[Narrator]

The prosecutor charges Alan Bregman with second degree murder since he can't prove Debbie's death was premeditated.

[Tom Guilfoyle]

He was arrested on August 4, the 39th anniversary of the day of the murder, which I thought was a nice touch.

[Roxanne Clark]

And all of a sudden there's a phone call. We're detectives from Miami. Allen is arrested. He gave us renewed hope that somebody is going to pay for it. So we just kept our fingers crossed.

[Narrator]

Prosecutors hope to beef up their case before the trial begins.

[Tom Guilfoyle]

A lot of things can happen in 40 years. Memories fade, evidence disappears, people pass away. That would make good witnesses remember. Beyond a reasonable doubt is a very high standard, higher than a civil case. It's the criminal standard and it's tough to get to now. The gun would have been a huge piece of physical evidence.

[Detective]

Then someone out of the blue made a call to us and said, I would love to speak to the detectives.

This person provided to us a very specific detail that hadn't been known at that time. We received this information that Allen had bought Debbie a firearm and specifically a top brake revolver.

We got a phone call from Joe Thompson. He lived in Champaign, Illinois and wanted to speak to us about our suspect, Alan Bregman.

This person was a coast guard friend of Allen.

Allen told Joe that he bought Deborah a small caliber handgun because he didn't want her walking in the dark without some type of weapon. We believe Alan came to her and probably told her, we need to break this off. She started defending herself, saying, what are you talking about? I got my divorce, you're getting yours.

Allen knew that Deborah had a firearm in that apartment.

He took the gun and we believe that's when the argument happened and he ended up shooting her.

[Narrator]

The prosecutor works with A medical examiner searching for forensic details that can help seal the case.

[Detective]

It was very important for us to meet with the medical examiner in this case, Dr. Emma Lu, and ask her what is her medical opinion as to what took place.

When they first came to see me, I was eager to help in any way I could. The original medical examiner who conducted the.

[Roxanne Clark]

Autopsy actually recognized a patterned injury on the left side of her neck. The pattern was reminiscent of a ring.

[Detective]

Whoever was wearing that ring was striking.

[Roxanne Clark]

Her, was beating her with it.

[Detective]

When we started digging for pictures that were provided by Honey BREGMAN to the 1977 detectives, there's a picture of Alan Bregman, and on the right ring fingers he had a gold nugget ring.

[Narrator]

The prosecution believes they have a strong case connecting Allen Bregman to Debbie's murder. Four decades after Debbie Clark's murder, the trial of 75 year old Alan Bregman begins. Alan pleads not guilty to the second degree murder charge.

[Detective]

We believe we have a pretty good case on Alan Bregman, but there's a.

[Narrator]

Wrinkle that could bring the case to a screeching halt.

[Tom Guilfoyle]

There was a quirk in the Florida statute that has since been corrected that there was a four year statute of limitations for second degree murder.

[Detective]

In our minds, she was murdered. How can there be a statute of limitation if you're murdered?

[Tom Guilfoyle]

The only way that was possible was the jury had to make a finding not only that he murdered Debbie, but he did it with a firearm.

[Narrator]

There's no statute of limitations on second degree murder if the killer uses a firearm.

[Detective]

We know that she was shot, strangled and beaten. If the jury would have found him guilty of second degree murder without the firearm, in essence, Allen would have walked out of that courtroom.

[Roxanne Clark]

This was the first time we saw pictures of the crime scene. To see those pictures and think of Debbie's final moments and how she must have felt. We know she was crying, she had tissue in her hand when they found her body.

[Detective]

One of the questions that the jury sent out was related to the order in which Debbie was killed.

[Roxanne Clark]

We know that she was beaten and she was shot, although I do not.

[Detective]

Know exactly which event came first.

[Roxanne Clark]

She was shot in the lower chest region and that caused a lot of internal bleeding and that's what finally killed her.

[Tom Guilfoyle]

In any homicide case, there's a lot of tension on both sides. And then when the jury goes out to deliberate, that waiting period is brutal.

[Roxanne Clark]

When they said the verdict was in, you could have heard a pin trap.

[Tom Guilfoyle]

There is a certain box on the jury form. That has to be filled out, firearm or not. And if they decided to not check that box, just find him guilty of murder, then he would have walked out that court a free man. We're all waiting in the hallway of the justice building for a verdict. It's a very, very tense time. Nobody knows, nobody has an idea what might happen when that verdict come back, as this one did. Guilty. It's a huge relief.

[Narrator]

42 years after Debbie was killed, Alan Bregman is found guilty of second degree murder by a firearm. He's sentenced to life in prison.

[Roxanne Clark]

I can't tell you just where your heart is until you hear those words. It's just such a glorious feeling.

[Detective]

This was the day that they'd been waiting for 40 something years.

[Roxanne Clark]

Debbie's mother is alive through the trial and we kept in touch with her daily. But she's very elderly. She couldn't make the trip down. When he was convicted and sentenced, she breathed a sigh of relief. She would say, I knew it. I knew it all along.

[Narrator]

Despite the conviction, Allen never admits to killing Debbie.

[Roxanne Clark]

We often wonder, why doesn't he just admit it? I just wish he could just come clean and say, this is what happened. I'm so sorry. I did love her. I loved your sister because that would be nice to hear. Debbie was young. She didn't get to do all the exciting things and be everything that she could be. A lot of good memories. When we were probably about 14, we would go Christmas caroling at very wealthy homes. She was a good singer and they would give us money and we would stop at the drugstore on the way home to buy our mother a Christmas present. And that's the kind of person she was. She was the best sister. She's never forgotten.

[Narrator]

Cold Case Files is hosted by Marissa Pinson, produced by Jeff deray and distributed by Podcast One. The Cold Case Files TV series was produced by Curtis Productions and hosted by Bill Curtis. Check out more Cold case [e-mail] it's.

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[Detective]

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[David Orvalle]

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[Detective]

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[Detective]

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For years, Tim Ballard has been championed as a modern day superhero.

[Tom Guilfoyle]

The first time I saw one of.

[Detective]

The kids from the video and it.

[Advertiser]

Like, changed my life. He was the face of Operation Underground.

[Narrator]

Railroad, a movement that inspired hope around.

[Advertiser]

The world by rescuing children from human traffickers. However, Ballard's crusade to save innocent lives has always hidden a darker secret.

[Tom Guilfoyle]

Oh, I think he's a pathological liar.

[Advertiser]

Beneath the accolades and the applause, a.

Dark storm has been brewing.

[Detective]

I mean, I can't find a time.

[David Orvalle]

That he's told the truth about anything.

[Advertiser]

Shocking allegations of sexual misconduct have surfaced, casting a shadow over his once unquestioned reputation. I am Host Sarah James McLaughlin and in this new season of the Opportunist, we explore the rise and the fall of Tim Ballard. Join us this October for Tim Ballard, Unmasking a Hero. Subscribe to a new season of the Opportunists Now. Wherever you get your podcasts.

It'S the holiday season and the perfect time to gift yourself with a new home for the new year. For a limited time, take advantage of incredible savings and incentives during Dr. Horton's it's yous Year Savings event. Going now through December 22nd, your perfect home for every holiday season is waiting for you. To find yours, visit any of our participating Dr. Horton communities or visit [e-mail] and discover the Dr. Horton difference. Dr. Horton, America's builder and equal Housing Opportunity Builder.