The After Show: Diary of a Killer

Summary

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20/20 After Show: Diary of a Killer

Host: Debra Roberts
Guest: Taji Smith, Senior Producer
Date: August 18, 2025

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Episode Overview

This episode of the 20/20 After Show revisits the harrowing case of Angela Bledsoe’s murder in Montclair, New Jersey—a case that stunned a picturesque, tight-knit community and led to a rare international manhunt. Host Debra Roberts and producer Taji Smith reflect on the investigation, the family’s heartbreak, and shocking post-trial developments. The discussion offers new details, behind-the-scenes insights, and a focus on how such crimes upend families and communities.

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Key Discussion Points & Insights

1. The Community Impact and Personal Connections

• Taji Smith reveals her personal connection: the story “happened in my backyard. You know, Angela...could have been me. That could have been one of my girlfriends.” (01:30)
• The case shattered the sense of safety in Montclair: “It became so clear that it could happen to anyone.” (01:53)

2. Angela Bledsoe: The Victim

• Angela was a 44-year-old, upwardly mobile financial advisor with a young daughter.
• The hosts discuss her accomplishments and solid family background, highlighting the “tight, tight knit family … salt of the earth, just very humble, wonderful people.” (03:38)

3. Discovery of the Crime Scene

• Police found Angela shot dead on her kitchen floor. Immediate observations included a blood trail, a gun cleaning kit, and her cell phone left conspicuously on a stool.

• James Ray, her partner and the father of her child, was absent from the scene.

  “They have a dead woman on the floor... and there’s no partner, husband, there’s no one there.” (04:45)

• Authorities quickly suspected the crime scene had been staged to appear like self-defense or accidental shooting.

  “There was a gun cleaning kit. There were shell casings, three shell casings that were lined up next to each other...it felt a little staged.” (06:56)

4. The Suspect: James Ray

• James Ray was a respected former cop, Marine, attorney, and martial arts expert who “ran several businesses.” (10:20)
• He was still married when he began his relationship with Angela—a detail uncovered through text messages analyzed post-murder.
• The relationship was marked by growing tension, his controlling behavior, and Angela’s increasing complaints, which became important to investigators. (12:26)

5. The Investigation & Evidence

• Crucial evidence included Ray’s handwritten letter to his brother, framing the killing as self-defense.
• Investigators, however, doubted his account due to forensic inconsistencies—Angela was shot from above, in non-confrontational positions (18:01):

  “According to those authorities, there was absolutely no evidence that would suggest that this was a case of self defense. The evidence showed that Angela had been shot in her back...in her head...in her chest.” (17:27–18:02)

6. The International Flight & Extradition

• Ray fled, evading law enforcement through multiple states before reaching Cuba.

• His journey was documented in a discovered journal:

  “He lives as a homeless man in Philadelphia. He hitchhikes...ends up in Texas. He takes a bus to Mexico, and from Mexico, he flies to Havana, Cuba.” (13:21)

• His capture and extradition from Cuba marked a highly unusual turn for a New Jersey homicide case, as the U.S. lacks an extradition treaty with Cuba.

  “Nobody seems to remember any case where Cuba was involved...an apprehension, let alone the fact it was a homicide in one of the most affluent towns in New Jersey.” (14:06–14:14)
  “‘If you commit a crime in the state of New Jersey, we will not forget, we will not forgive, and we will find you.’” (14:31, Taji quoting law enforcement sentiment.)

7. The Trial and the "Diary of a Killer"

• At trial, forensic experts, including Howard Ryan, meticulously reconstructed the crime, disproving Ray’s self-defense claim.
• Ray’s calculated post-crime letters and journal entries further pointed to premeditation:

  “Very, very calculated case for self-defense, but the prosecutors weren’t buying it.” (19:14)

8. The Case’s Shocking Conclusion

• Ray was found guilty but, before sentencing, was found dead in his jail cell—suspected suicide, occurring ironically on Father’s Day.

  “James Ray isn’t—we think he’s dead. His family’s saying he’s dead.” (20:28)

• Under New Jersey law, because Ray died prior to sentencing, he was never officially convicted—an outcome that was painful for all parties:

  “She [prosecutor Michelle Miller] had to move to dismiss the case. And when I talked to her, and I quote this word for word, she told me it was the worst feeling in the world.” (24:41, Taji quoting Miller)

9. The Family’s Aftermath

• Angela’s daughter, now thriving and an honor student, was taken in by her aunt Lisa, exemplifying the resilience of the Bledsoe family.

  “Despite it all, you know, it speaks to the strength of the Bledsoe family and how close they were.” (22:23)

• The hosts reflect on the tragedy of a custody dispute devolving into homicide and the long-term impact on both families.

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Notable Quotes & Memorable Moments

• On Community Impact:

  “That could have been me. That could have been one of my girlfriends.” – Taji Smith (01:30)

• On the Crime Scene:

  “Detectives will talk about finding a scene where it doesn't look quite authentic ... clearly they could tell that it felt a little staged.” – Debra Roberts (06:21)

• On Evidence and Motive:

  “In this case, it was never a question of who killed Angela, but this was really about why.” – Taji Smith (02:38)

• On Angela’s Character:

  “She owned her own brownstone by the time she was 27… she was financially secure and she wants a family and she wants children.” – Taji Smith (10:40)

• On Ray’s Flight:

  “He takes this circuitous route... lives as a homeless man...ends up in Cuba.” – Taji Smith (13:21)

• On the Prosecution’s Pain:

  “She told me it was the worst feeling in the world.” – Taji Smith, quoting prosecutor Michelle Miller (24:41)

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Timestamps for Important Segments

• Personal Connection and Family Background: 01:30–03:38
• Crime Scene Discovery and Staging: 04:27–07:58
• James Ray's Profile and Relationship with Angela: 10:12–12:15
• Evidence and Law Enforcement Perspective: 17:27–20:08
• International Flight & Extradition: 13:21–15:14
• Shocking Twist—Ray’s Death and Legal Aftermath: 20:28–24:41
• Family’s Recovery and Resolution: 22:23–24:41

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Closing Reflection

The episode closes on the enduring trauma faced by Angela’s loved ones and the dogged pursuit of justice by law enforcement and the prosecutor—even when justice takes an unpredictable, heartbreaking path. The story is a reminder that domestic violence can affect any community and that its aftermath reshapes families for years to come.

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If you or someone you know is struggling, help is available. Call or text the Suicide and Crisis Lifeline at 988 for free and confidential support.

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Transcript

[A]

Foreign hello, everybody. I'm Debra Roberts and welcome to 2020 the After Show. This story is one that I will not forget and probably most of our viewers and you listeners won't either. It was a murder investigation that shocked a small community, one that was known to feel safe and very picturesque. A beloved mom, Angela Bledsoe, shot to death inside her home in Montclair, New Jersey. Now, many of you learned through our 2020 episode called Diary of a Killer that I reported this case. I spoke with Angela Bledsoe's family, along with investigators about the 44 year old mom who had been a financial advisor and the murder case that led to an international manhunt. This story was nothing short of mind boggling, and it led to an unforgettable twist. And I am so looking forward to catching up to talk about on today's 2020 the After Show. Joining me is senior producer Taji Smith. Hey, Taji.

[B]

Hey, Deborah. How are you?

[A]

I'm good, I'm good. You and I are always bumping into each other in the hallway.

[B]

Yes, we are.

[A]

When we're not working on stories together. And you're always giving me the scoop on the latest, but this one you and I worked on a few years back.

[B]

A few years back, yeah, yeah.

[A]

And it was one that you get really passionate about stories and I get the impression from you that particularly when there's family, like really deep family connections to these stories, it really moves you.

[B]

Well, yeah, yeah, especially this one because it did happen in my backyard. You know, Angela, when I look at this story in her case, I'm like, that could have been me. That could have been one of my girlfriends. I mean, she had a young daughter, same age as my daughter. We lived in a, you know, same community, live very similar lifestyles. I'd seen her around town, so.

[A]

Oh, so you had a sense of who she was?

[B]

I had a sense. And you know, when people turn to true crime, sometimes it seems like, wow, you know, we hear this. This isn't the type of thing that would happen where I live. But when this story broke in Montclair, New Jersey, it became so clear that it could happen to anyone.

[A]

Yeah, yeah. And, you know, Angela was a woman of color, upwardly mobile, you know, solidly upper middle class woman, a financial advisor. Just the type of woman who just seemed like she was on her way to a successful life and. Except she had this significant other that turned out to be a problem. What attracted you to this story in the beginning other than the fact that clearly this was somebody you Related to. But you really clearly thought that twists and turns would be interesting for our viewers.

[B]

Oh, my gosh. Like, we love anything with a plot twist, right? Like where there are twists, turns, nooks, crannies. And in this case, it was never a question of who killed Angela, but this was really about why. And, you know, this case just had so many elements. There was so much here that we don't always get. Audio recording, a diary, conversations that James Ray was recording, you know, with his friends and family just moments after the killing occurred. So there was just so much there, so much to dig through and get into.

[A]

Yeah, I remember you met her family, her parents and her daughter. And you convinced me that, that I should be involved in this story, which I was quick to jump into. But you were really touched by her parents and also the fact that her daughter now was left without her mother. And that was a big part of the story. Trying to convince them to sit down and talk with us about their memories of Angela.

[B]

Oh, absolutely. I mean, you remember her parents, right? Salt of the earth, just very humble, wonderful people. Her dad, as you recall, was a lifelong educator. They were churchgoing folks. They raised their kids. They were tight, tight knit family. And I remember we were both struck by just how broken up they still were about the case and about their daughter's death. But, yeah, certainly this was a case that I lived with for a long time, for years, because it did take several years for it to actually go.

[A]

To trial and for it to all play out. Well, let's talk about the beginning of the story. It was October 2018. Investigators are called to Angela's home in Montclair, New Jersey. And it's. It's a pretty rough scene.

[B]

It's a gruesome scene.

[A]

Gruesome scene. She is dead on the floor. Talk to us a little bit about what they found when they got there. Because oftentimes these stories start off with the suspicion that either there's a killer on the loose or a crime scene that looks a little suspicious. Talk to us about what the police found when they first got there.

[B]

So when police first get to the scene, they discover Angela Bledsoe shot to death on the kitchen floor. They see a blood trail that leads from the living room into the kitchen. They see firearms. They see a gun cleaning kit. They see her cell phone on a stool. And they're just not sure what to make of the situation. What they don't see or who they don't see is her significant other, the father of her child. So they have a Dead woman on the floor in an affluent community in a big house, you know, and there's no partner, husband, there's no one there. And so that was kind of curious for them. But what they did have was a call. James Ray, who was Angela's, the father of her child and her significant other and his brother had called and said, you know, you need to go take a look at this house in Upper Montclair. My brother's left me a message and he said that there's something going on in the house. And when police got there, that's what they. They discovered Angela dead on the floor.

[A]

But her daughter was not there.

[B]

Her daughter was not there.

[A]

Fortunately, you brought to our story Howard Ryan, who was a former state detective.

[B]

Former state police officer, he'd been with the New Jersey State Police for 25 years, retired and became a crime scene investigator. Somebody who goes into crime scenes and figures out for, you know, prosecutors and law enforcement what took place.

[A]

And that was very important too, because when we're unspooling these stories, it's always about trying to help the viewer understand what was significant. And when the police got to the house, what they found, and you described the scene with the phone, and initially, and this happens in a lot of the stories that we cover, detectives will talk about finding a scene where it doesn't look quite authentic. It's made to look like, you know, in this case, maybe she was playing or dealing with a gun. But clearly they could tell that it felt a little staged. They didn't feel like this was self inflicted.

[B]

No, absolutely. Howard Ryan goes into great detail in our show that there was a gun cleaning kit. There were shell casings, three shell casings that were lined up next to each other. Howard believed, you know, and led authorities to believe that the cell phone that had been placed on the stool, they learned that that was Angela's cell phone, but that it had been placed on the stool after she had been killed. What was interesting about this case, and you'll remember, is this letter.

[A]

Yeah, right.

[B]

He leaves a letter first for his brother. And the letter really is James Ray's version of events. And he said that there had been a fight and that Angela. Or an altercation, verbal dispute. He says his version of events again, that he was cleaning his guns and Angela picked up one of the guns pointed at him. And he felt like his life was in danger.

[A]

And that he had to flee.

[B]

Yes, that he had to flee. And what Howard Ryan found and what authorities believed was this didn't look like self defense. No, matter what James Ray said in his letter to them, it looked like the crime scene had been staged and made to look like it may have been self defense.

[A]

Yeah, which happens so often in these stories we cover. Well, I want to dig deeper into that with you, but we're going to take a break and when we come back, we're going to jump right back into this investigation and why federal authorities, the FBI, got involved after they got an unexpected lead about Angela's killer. So stay with us. Foreign.

[C]

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[A]

Hi, everybody. I'm back with Taji Smith, senior producer here at 2020, and we are discussing a story that we worked on together, the Angela Bledsoe murder case. And we were just talking about the surprising evidence that police found when they got to the crime scene and just sort of piecing this all together. There's a note from Angela Bledsoe's significant other, the man who would ultimately be found responsible. As you said, detectives weren't sure what to make of this scene. And let's talk about James Ray and what we learned about him. She was a very smart, bright, investment banker type.

[B]

Yeah. Financial advisor, very well respected.

[A]

And what about him? He also, too, was a very respected guy. Had been a former cop.

[B]

Oh, yeah, former cop, former Marine. An attorney. You know, he ran several businesses. He was a martial arts expert. Very interesting man. There's so many nuances to this story that we really couldn't get into. And that's why I'm so glad we're here today.

[A]

Yeah. Because talking about behind the scenes is what we give listeners a chance to learn a little bit more about.

[B]

This is a story about lifestyle, you know, and here you had Angela when she meets James Ray. You know, she's living in Brooklyn. She owned her own brownstone by the time she was 27 years old. Huge feat. She's financially secure and she wants a family and she wants children. And she meets James Ray, and he's living this great lifestyle. I mean, he's living this upper middle class, African American lifestyle in Montclair, New Jersey. You know, he's a member of a Greek organization, you know, big fraternity. He's got a great car. He's also got a family.

[A]

Yeah, yeah. A family that she doesn't really know all the details about that she doesn't.

[B]

Know the details about. But she meets Ray, they begin a relationship, and, you know, she finds herself pregnant. And unfortunately, you know, he's still married and he still has his family. Right after Angela's murder, what we find through her text messages is that she's struggling with the fact that, you know, there had been this other woman and this other family, and they live apart for a while before she moves into that home in Upper Montclair. After Ray manages to get his first family out of the home, by the way. And so now she's here, and she knows she's living in essentially another woman's home. And she's angry about the way that he treated her during her pregnancy. He felt like she hadn't done enough for her and the baby. But she's taken a risk and she's hoping to start her own family.

[A]

But yet there was a lot of tension in their relationship. And we explore that in the story. And clearly things start to go south.

[B]

Oh, yeah. After a while, I noticed every time.

[A]

She called, she was complaining about him more and more and more. She would just text me little things he would say, little things he would do. He became a little paranoid and he became more controlling after a while. That clearly is a place that police begin to look because her relationship is falling apart. Police start to use all of these details to kind of shape their case. And we talked to investigators, attorneys in this case, and there was whole timeline here, but just those little crumbs, the letters that were left, the audio recording. And this story also involved a rare international extradition from Cuba. So Ray is on the move. Police are trying to. They've got a woman here who's been killed. They can't find the guy who is responsible. And let's talk about. Cause that was One of the things I think that was so intriguing about this story, he is on the go and he's on the move and they cannot find him. And he winds up in Cuba.

[B]

He ends up in Cuba. And how he gets there, I mean, he takes this circuitous route, which we learn about later in a journal that's found when they catch him in Cuba. But we learn through James Ray's own handwritten journal that he lives as a homeless man in Philadelphia. He hitchhikes with truck drivers, he ends up in Texas. He takes a bus to Mexico, and from Mexico, he flies to Havana, Cuba. When they finally said that they had apprehended him and that he had gotten all the way to Cuba was just mind boggling. Nobody seems to remember any case where.

[A]

Cuba was involved, where there was an.

[B]

International flight, a pursuit out of the.

[A]

Country, an apprehension, let alone the fact.

[B]

It was a homicide in one of the most affluent towns in New Jersey.

[A]

I think he felt like, oh, America.

[B]

Doesn'T have an extradition treaty with Cuba, so I'm going to be here and forget about it.

[A]

But that's not how it works, buddy.

[B]

If you commit a crime in the state of New Jersey, we will not forget, we will not forgive, and we will find you.

[A]

This story was so fascinating that way because we had a map to help the viewer understand his whereabouts and so forth. And Taja, you and the rest of the team did a great job sort of shaping all of that. So after he's apprehended, because eventually they do catch him, they get a tip.

[B]

And I still, you know, as a journalist, I still don't know where the tip came from. James Ray was in Havana, Cuba, but he's not there. Long before he's apprehended, we see him being, you know, led off of the tarmac onto a U.S. you know, charter plane and taken back to the United States.

[A]

And we talked to one of those investigators who rode with him. It's rare that we get insight into a person who has found guilty murder. But in this case, in his own words, in this diary, I mean, and I want to talk about that because that was so fascinating. We're going to take a break, though, and when we're back, we're going to talk about that and also the shocking twist in this case and what we know about Angela's young daughter today and how things wound up. So stay with us.

[B]

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[C]

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[A]

We're back talking about our episode of 2020 called Diary of a Killer. Angela Bledsoe was murdered and found in her Montclair, New Jersey home. Her boyfriend, James Ray iii, fell under suspicion. He fled the country. He was extradited back here. Taji Smith worked on this story for a very long time along with our team. And let's talk about the trial. So when investigators are trying to piece this all together, initially, you know, Ray is claiming it was self defense. Of course, investigators don't believe it was self defense. They sort of sketched out how they thought she was shot. And she was not shot in a way that would have been lunging toward him.

[B]

Right, Exactly. Like according to investigators. And when we say investigators, we mean detectives from the Essex County Prosecutor's Office in New Jersey. We mean police officers from the Montclair Police Department, and we mean Howard Ryan, who was hired by the Essex County Prosecutor's Office to sort of figure out what happened that day. According to those authorities, there was absolutely no evidence that would suggest that this was a case of self defense. The evidence showed that Angela had been shot in her back.

[A]

I remember her.

[B]

In her head.

[A]

Yeah.

[B]

In her chest. The evidence, according to authorities, the prosecutor led them to believe that she had been shot from above, that someone stood above her and shot her.

[A]

And that was critical.

[B]

And that was critical when they presented that while she was lying on her back. So, you know, that physical evidence, the fact that you can see that she crawled, you know, on her hands and knees from the living room. When authorities look at the blood trail, it showed that she had crawled on her hands and knees from the living room to the kitchen. And she was shot from above, in that kitchen. Okay. And so she was shot in the back, but she was shot from above, and that was critical.

[A]

And also. And they didn't see any signs that she was, like lunging toward him and trying to attack him. And that was very critical in how we presented our story. Absolutely. You got a crime board for Ryan to kind of walk me through to show me all that key evidence, which when we are telling these stories, I mean, that's so important for our viewers to be able to see how these things played out in court and also in the investigation.

[B]

And we would be remiss not to say that investigators, the prosecutor, Michelle Miller also, you know, thought that Ray's own writings helped implicate him. And what's interesting and ironic to me as a producer is he writes this letter to his brother to say, this is what happened. This is what Ray believes happened. There was an argument, and I know I'm not going to get a fair trial and no one's going to believe me, so I have to go on the run, take care of my daughter, make sure she goes on the trip that I've planned, continue to give her golf lessons. He drops off the golf clubs and he is setting what he believes. Remember, he's a lawyer. Right. Very, very calculated case for self defense, but the prosecutors weren't buying it. And the physical evidence, according to those investigators, just did not support this claim.

[A]

When we reported this story, Ray had been found guilty. He was awaiting sentencing. Michelle Miller felt very strongly about this case and she really felt satisfied that she had argued this case. And then you and I were talking with her and there had been a.

[B]

Big, A big, A big twist.

[A]

Yeah.

[B]

In fact, Michelle was away when this twist happened. One of our producers received a phone call from Ray's family saying he'd been found dead in his jail cell. And that's when I alerted, you know, you and our team to say, wait a minute, James, Ray isn't. We think he's dead. His family's saying he's dead.

[A]

And we were still hoping that maybe we might get an interview with him. We were really pushing forward in this story, and so often it's sort of lost in these stories. And I think one of the things that we pride ourselves in here at 2020 is that we so deeply focus on the victims, the families, people whose lives have been affected. And his family so wanted to have that day in court and to be able to talk about how this had affected them. And Angela's family was so deeply affected by this, but also so Looking forward to having their opportunity to speak, speak in court about how their lives have been affected. And so James Ray is found dead. Of course, it's deeply suspected that he had taken his own life. It was shocking to everyone, including the prosecutor in this case. And what was interesting was that there was a big question about what would happen. So now Ray had been found guilty and now we were awaiting the sentencing. Angela's family so wanted to be able to speak out in court, in victims impact statements, to talk about their lives and so forth. So this was the big moment in this case. And then of course, he's found dead in his jail cell and the question becomes, did he take his own life? So that's an investigation and you and I were sorting that out. At the end of the story, we had had an opportunity to meet Angela's daughter. And of course, we sat down with the family. They were so heartbroken. Before we get to the case and where it all ended, what about the family? I mean, her daughter was so impressive and so, so lovely. How are they doing? Because you often keep up in these stories with families.

[B]

I do. She's doing great. An honor student. She's thriving. She's beautiful. Despite it all, you know, it speaks to the strength of the Bledsoe family and how close they were. Her aunt Angela's sister Lisa, who was prominent in our show, was an empty nester. She was looking forward to, you know, life with her husband. But she took on the blessing of her niece, of her sister's daughter. And really what we did learn, sadly, that this was this is a case about two people who really love this little girl. And at the root of this, this was a couple who was going to split. And they both wanted this child and they both wanted the best for her. And unfortunately, it imploded and ended in this tragic end. But it was rooted in them. James Ray wanting his daughter and not wanting her to be taken away from him. And Angela Bledsoe also wanting her daughter and wanting to raise her without him.

[A]

Yeah, this bitter dispute which happens in so many of our stories. Well, let's talk about today, where it all stands. I mean, the surprising ending to this story. And we didn't know what would actually happen with the case. So what. I mean, breaking news. You've got breaking news here?

[B]

Well, yeah, I do. I do have breaking news. So, you know, I've stayed in touch with the prosecutor, Michelle Miller, about this case and she told me that she's able to confirm that James Reed III did in fact take his own Life. That's the first thing. Now, we also know that while he was found guilty of the murder, he was not convicted.

[A]

He was not officially convicted.

[B]

He was not officially convicted. In the state of New Jersey, you are not convicted until you are sentenced. And he was found dead in his cell, ironically, on Father's Day of all days. And so for months, we just didn't know what was going to happen with the case. For months, we didn't know if it was suicide or if he died of natural causes. Michelle Miller recently told me that she had to dismiss the case.

[A]

Wow.

[B]

And she said, I avoided it, and I avoided it. And so Michelle Miller, that passionate, dogged prosecutor who fought so hard for justice for Angela's family, she had to move to dismiss the case. And when I talked to her, and I quote this word for word, she told me it was the worst feeling in the world. Michelle said even though Ray wasn't convicted, she and the family find comfort in the fact that he did not die an innocent man.

[A]

I can imagine. I can imagine. I mean, for the family, but specifically for her having worked on this case. Sometimes there's a surprise ending. There is, yeah, A better end to these stories. But, Taji, I gotta tell you, it was one that I think viewers won't forget. Listeners here, I think will remember this story and can go back and find it, of course, in our 2020 files. It was such a fascinating story and you did a great job on it.

[B]

Thank you. So did you. I was glad to work with you on it.

[A]

Thank you for coming. Coming by. Well, it's always great to get a chance to talk a little bit more about our stories behind the scenes. We also want to note that if you are struggling with thoughts of suicide or worried about a friend or loved one, call or text the suicide and Crisis Lifeline at 988-for-free and confidential. Emotional support 24 hours a day, seven days a week. That will do it for us on this episode of 2020, the After Show. The 2020 After show is produced by Amira Williams, Susie Lu and Sasha Aslanian with Matt Lombardi, Brian Mazerski and Alex Barenfeld of 2020 Theme music by Evan Viola. Janice Johnston is the executive producer of 2020. Josh Cohen is the director of podcasting at ABC Audio. Michelle Margulis is the operations director. Laura Mayer is the executive producer.