A Deep Dive into the Life, Career, and Crimes of Sean Combs
Alison Stewart: You are listening to All of It on WNYC. I'm Alison Stewart. Listeners, we want to give you a heads up and a content warning ahead of our next segment. This interview will touch on topics surrounding domestic violence, rape and sexual assault, specifically involving women. This might be time for you to put on some headphones if you're around younger listeners or find some time to listen later on WNYC. If at any time you need support, please call the national Sexual Assault Hotline, 1-800-656-4673. It's available 24 hours a day.
A docu series shows the hip hop mogul Sean Diddy Combs leading up to his high profile trial. In October, he was convicted and sentenced to more than four years in federal prison for transporting individuals across state lines for the purposes of prostitution. He was acquitted on more serious sex trafficking and racketeering charges. The series is called Sean Combs: The Reckoning. We learn how Combs got to this point in his mid-50s. The film goes all the way back to his younger days in Mount Vernon, New York, his life as a New York City party promoter and as an artist and producer. We also hear from some of the people he hurt along the way.
A review in The Guardian states about the series, "It does feel like a grimly necessary one. Over the course of four episodes, the director Alexandria Stapleton paints a pattern of behavior that starts to feel horribly inevitable. Sean Combs: The Reckoning is now streaming on Netflix. Director and executive producer Alexandria Stapleton joins us to discuss. Alexandria, thanks for coming to All of It.
Alexandria Stapleton: Thank you for having me.
Alison Stewart: The story of Sean Combs and his victims has been covered heavily in the press. What parts of the story did you hope to illuminate?
Alexandria Stapleton: I think that the goal of this series was to take the two dimensional headlines that were happening in the news and to really give context behind what was happening, the stories of the victims, and more information about, how do you even get to a place-- how do you arrive at a place where all of this behavior could allegedly happen and no one is talking about it? How did he wield so much power?
Alison Stewart: What was the question you wanted answered first?
Alexandria Stapleton: Oh, goodness. [laughs] I don't know if there was one question. I was really drawn to understanding the source of power. I think that's what I was really interested in trying to unpack, how does one get away with all of this? It seemed as though he was dangling a carrot with artists and a lot of different people, like, "Come do this. Come work for me for a year, but I'm not going to pay you." My head was like, "How does that even happen? It seemed to be also like a lot of patterned behavior over the course of his career.
Alison Stewart: In your mind, when you look back on it, did he always have the sense of what power is and what power can get you?
Alexandria Stapleton: I think so. I think that perhaps he saw at a very young age what-- He started off as the party promoter. I think that people chalk that up as like, "Oh, that's just teenager, young adult stuff. That's college behavior." I think that there was a power dynamic even in those situations, him promoting parties on college campuses. We interviewed Joi Dickerson-Neal, who told us about her allegations of sexual assault. It was really harrowing for her to say-- No one wanted to help her, no one wanted to say anything because they were afraid of not getting tickets to his parties. Then you throw more money in that story, you throw more power in that story, and then you can see how things could escalate.
Alison Stewart: Diddy has been a monumental figure in both hip hop and Black culture. He's also a really good businessman. How did his relevance in hip hop, both the culture and the movement, how did it help you guide the narrative of the documentary?
Alexandria Stapleton: I think that what ended up happening is that over the course of four episodes, we really land in his ecosystem of Bad Boy. That's the meat and potatoes of the series. The time that we cover, it's really understanding how did Bad Boy-- how was it created? How did it run? All the way up into his arrest and indictment.
Alison Stewart: Grammy Award-winning rapper and executive producer 50 Cent, Curtis, 50 Cent, Jackson, he's been skeptical of Diddy in the past. They've had a rivalry in the industry. He served as the executive producer on this documentary series. Why do you think it was important for him to be involved? Why did he want to be involved?
Alexandria Stapleton: It's important to remember that when we started this project, there was no arrest, there was no indictment. All that had happened really was Cassie's lawsuit dropped, and then--
Alison Stewart: His girlfriend.
Alexandria Stapleton: Yes. Then there were a few other lawsuits. This was early in the story. There were just so many people that were really afraid of talking. 50, I think, him coming on board and us partnering together to do the show, it offered a shield of protection in a way. I think people mentally felt like, "I know that you're not taking my story, Alex, and going and giving it to the media or giving it to Sean." People, I think, felt safe to share. That was probably the biggest thing that having him attached to the project helped with.
Alison Stewart: A docu series reflects on the rise and fall of hip hop mogul Sean Diddy Combs. Director and executive producer Alexandria Stapleton is here with me now to discuss the series Sean Combs: The Reckoning. It is now streaming on Netflix. You begin with footage of him amid the trial. Why did you want to start there?
Alexandria Stapleton: [chuckles] That footage was-- I remember when I first watched it, it was jaw dropping. I felt like getting into the story and realizing behind closed doors, what was his attitude? What were the conversations that were going on with him and his team? It was really fascinating. As a documentarian, those are the types of things that are very interesting to put into your stories.
Alison Stewart: Let's listen to a clip from Sean Combs: The Reckoning. This is six days before Combs' arrest. He calls his attorney for an emergency meeting over the phone. Listen to this.
Marc Agnifilo: We need the core theme to be, "You didn't do anything wrong." You didn't do anything wrong on any front, and you've come to New York to face things head on. If anyone's ever paying any attention to what you've actually been doing, you've handled this with complete honor.
Sean Combs: I don't think it's working. I've listened. I've been a superb client, as you said. I've jumped on a plane, I'm coming to New York, but I'm just like, I'm just running around waiting for a shoe to drop.
Marc Agnifilo: We're losing sight of the big picture, man. It's the middle of September, and there's still no indictment. That's--
Sean Combs: No problem. Then you have to have a spokesman, you have to have some sort of comms to constantly be pushing that mark, because you may just be a person that just does-- You just may watch CNN, you know what I'm saying? There's 9 billion people in the world, and 7 billion of them is on Instagram and TikTok. You are at the wrong place looking to see what the people who are the possible jurors are thinking. We have to find somebody that'll work with us, whether they from this country or from another country. It could be somebody that has dealt in the dirtiest of dirty business of media and propaganda.
Alison Stewart: What do these first few moments tell you about Sean Combs?
Alexandria Stapleton: He was fighting for his freedom and fighting for his life. There was no indictment yet, but he still-- There was a pulse, I think, that he knew what was coming down the pipeline. I think it was fascinating that he was filming it.
Alison Stewart: That is interesting.
Alexandria Stapleton: laughs] Just that fact alone in the height of all of that, you're sitting in your hotel room and you have someone who you don't-- some guy who's not a part of your team filming you. That was very odd to me when I first watched it.
Alison Stewart: He spoke to comms He says comms in the middle of us. Like, "Oh, this is your comms. This is your propaganda that you--" [unintelligible 00:09:14] propaganda, but this is what you are saying to get your story out.
Alexandria Stapleton: Correct.
Alison Stewart: He understood that.
Alexandria Stapleton: He understood that. He's a genius at it. Then I think once we saw that, we were able to build this case to show the pattern of him understanding that at a very early age and how he perfected the art of it. Then you see what happened during the trial and how things did unfold.
Alison Stewart: How did you keep your documentarian hat on so that you didn't feed into the propaganda or the marketing of it?
Alexandria Stapleton: Of course, the mission is to show both sides. I would have loved to have gotten an interview with Sean Combs, or even his attorneys or more people on his team. I think that we did show both sides. Really, that footage shows you his side of things and what he was thinking and feeling in real time.
Alison Stewart: There's someone in the series who brings up the idea that people's perception of Sean Combs might be different based on how they follow him, whether they follow him on CNN, whether they follow him on TikTok. He brought it up himself. How might someone who isn't necessarily a fan or follower of Sean Combs, how might someone think about his career, think about him?
Alexandria Stapleton: I think from the surface level, he's been a massive contributor to the culture, to hip hop culture, to Black culture. He has really been a giant force who's been involved from everything from music to elections to-- so many things. A lot of that is positive. I think that for people that don't know everything about all of the recording industry part of him, I think that they probably resonate that he's a mogul and a billionaire and one of those very amazing American stories.
Alison Stewart: Let's go back a little bit. He was born in Harlem. He moved up to Mount Vernon, New York. How did the people who knew him when he was in Mount Vernon, and his mother as well, was an important influence, how did they describe the family?
Alexandria Stapleton: I interviewed a close friend, someone who grew up with him, in the same house as him upstairs, Tim Dog. Tim described the family life. His father was murdered tragically when Sean was very little. He grew up with a single mom who I think worked really hard to make ends meet, and to raise her son. He was fortunate enough to go to private school, where I think that also shaped the way he saw the world and exposed him to things, and went from my understanding, being bullied when he was young to coming into his own skin and understanding again, how do I assert control because I am the underdog? What do I do to flip the script and to flip the narrative?
Alison Stewart: He went to Howard University, HBCU. He dropped out, though, to pursue a career in entertainment. [laughter] He gets to the height. Goes to Howard. "No, I'm going go to entertainment now." What was the allure of entertainment and of business at the time?
Alexandria Stapleton: Sean's the only one who could really answer that question. From the outside looking in, I think he liked attention. I think that's also something that we could trace that went back to his childhood. Tim Dog and even other people that we spoke with off camera talked about how he dressed as a young kid with fur coats on, and the hats cocked to the side. I think he liked attention. I think he liked being in the middle of chaos, being that eye of the storm. I think that that's a place where he probably feels most comfortable.
Alison Stewart: Was he playing A role, or was that really him, or was it a combo?
Alexandria Stapleton: Probably a combo. In watching the footage-- He's filmed himself for decades.
Alison Stewart: You got to look at the footage. That's why I'm asking. When you look at the footage, you can see--
Alexandria Stapleton: You can see the different dynamics, the levels. I think he has different modes. I think when you do reality TV for a very long time, you start to understand when you're being filmed, like, "This is really me, but I know I can edit this part out," or, "This is me playing to the camera." Just the different modes that he was in. It became obvious at certain points with looking at that footage, like, "Oh, this has really nicked him."
I think when you see the lawsuit by Dawn Richard drop, that is a moment in the footage that we had where it felt like there was an artery that was nicked with that. That really got to him. He was very upset for whatever reason. Then there's times where-- like in the footage that you rolled, there's a moment in the film where he actually motions to the guy who's shooting to come closer to capture what he's saying. It's a mystery that only he can really answer, like, how serious does he take things? What is really going on in Sean Combs' head?
Alison Stewart: You go back to 1991. Folks didn't know this on our staff, but being from New York, it was the college crowd riot that happened that he was responsible for in a certain way. It happened at City College. There was-- Oh, gosh, it was a City College gymnasium. It was a stampede that occurred outside of it for a show that he was putting on one. Why was it important to include in the documentary? What did you want to show with that?
Alexandria Stapleton: How the dimensions of Sean being involved with really tragic events and how-- It's almost like out of tragedy, he's able to-- Chaos is a ladder is a saying that I always think of. I feel like that is something about Sean's life. It's like chaos is a ladder. That was such a horrible incident. You could argue he was responsible for or wasn't. There's a lot of different ways to look at that. Ultimately, he was found responsible for overselling those tickets.
How he managed to go out there in public and talk to the press about that event was very fascinating to me. He was like, "Mea culpa, this is horrible." He has this face that he does and a cadence in his voice when he's talking to the press and wants everyone to know how much he feels, how awful this is. When you start to see that pattern of incident after incident after incident, all the way up to the tape that came out where he was brutally attacking Cassie, and he comes out with an apology video. When you pair that up against the hit the press conference from 1991 at the City College event, it's almost identical-
Alison Stewart: Wow.
Alexandria Stapleton: -in its energy.
Alison Stewart: We're talking with Alexandria Stapleton. She is the director and executive producer of the series Sean Combs: The Reckoning, which is now streaming on Netflix. In the documentary, there's talk of Combs' abuse when he wasn't as famous. For example, Joi Dickerson-Neal sued Combs under the New York State Adult Survivors act in November of '23. In the lawsuit, she alleged she was drugged and assaulted by him in 1991. Why did Joi Dickerson feel that it was time to come forward?
Alexandria Stapleton: She said that when Cassie dropped her lawsuit, that that gave her the ultimate confidence to come forward. I think that it was like a Pandora's box that opened for him, and she found the strength to bring forward her case.
Alison Stewart: She was among the first of a hundred civil cases filed against Combs, including his longtime girlfriend. We've talked about her, Cassie Ventura. Why do you think his relationship with Cassie became the focus of the story and the focus of the news?
Alexandria Stapleton: Cassie's very famous. They were very public, very famous couple at the time during their relationship. Unfortunately, for a lot of other victims who don't have that type of wealth or power or visibility, on its face, it doesn't feel fair that so many other people can be victims but don't have that platform. I think that the flip side of that is because she was so famous and so visible, that it also put a lot of attention on him and gave people like Joi Dickerson-Neal the courage to come forward.
I think that's why the press probably ran with that story. Also, the allegations that she made were deeply disturbing. I'm not trying to measure pain or anything like that, but the details of the sex workers and details about what was expected of her, and all of those types of things. My jaw was on the floor. I think it was very peculiar.
Alison Stewart: We've got a sound bite from Joi Dickerson-Neal's mother. She wrote a letter to the Combs' parents. Tell us a little bit about this before we play it.
Alexandria Stapleton: Joi found a letter-- Her mother had passed away, and she found a letter that was written to Sean's parents. She didn't know that his father had passed away, and it was gut wrenching to hear her read.
Alison Stewart: Let's take a listen.
Joi Dickerson-Neal: Dear Mr. And Mrs. Combs, I'm writing you to inform you of something that your son did to my daughter. One weekend while visiting my daughter, I awoke to her screaming in the middle of the night. She told me that she was dreaming about Puffy. I asked her why she was screaming and who is this Puffy person that he would cause her to have nightmares. I was shocked and mortified to hear her story.
She told me that several people have come to her to inform her that your son has made an obscene videotape of her without her knowledge. He videotaped him doing something sexual to her. Apparently, your son shows these tapes at parties on large screen televisions. I realize that this may be hard for you to believe, but if I hadn't heard this story from my daughter's own mouth and looked into her eyes, I would have scarcely believed that any individual would compromise another person's dignity in this manner.
Alison Stewart: You hear how important dignity is to her. Why is that?
Alexandria Stapleton: That's what her mother instilled in her. Joi was from Harlem and didn't grow up with much, but the one thing that she said that her mother made sure that her kids had was dignity.
Alison Stewart: In this four-part docu series, there's lots of great archival footage and audio and images from all different periods of his life. Why was it so important to tell the story in images?
Alexandria Stapleton: I think that that helps-- it helps people connect to the material on a visceral level, when you can actually see things and feel like you're there.
Alison Stewart: Did you have any rule of thumb or any rules about when to use these old photographs?
Alexandria Stapleton: As much as we could. The archival team on this project and my editors, we had so much footage. There's so much that didn't even make it into the series. I feel like that's why it's potentially connecting with people and people that don't even follow hip hop or don't even know anything about Sean Combs. You really are taken back to these time periods, and going through-- understanding on a macro level what he was doing as he's gaining notoriety and fame and fortune, but the underbelly of that. I think to be able to expose him in his very public life--
There's a clip with Andy Cohen that we used, and it's intercut with this perfume ad with him and Cassie. They're running around and being very sexual. It flirts with violence in a disturbing way. Then we cut to him on Watch What Happens Live. I love that show. He was a guest, and he's like, "That's a fantasy of mine." You're seeing these layers, and like, wow, he's telling you out in public what he likes. He's selling product with this woman that he's doing all of this stuff with. We felt that that was really fascinating to ploy with all of those types of things.
Alison Stewart: What did you learn working on this?
Alexandria Stapleton: That's a really good question. I learned a lot of things. I was also in New York during that time period trying to work in the film industry. It brought up a lot of memories for me. I think in the post MeToo world, the question is, how far have we come? I think the answer is maybe not far enough.
Alison Stewart: The name of the series is Sean Combs: The Reckoning. I've been speaking with its director and executive producer, Alexandria Stapleton. Thank you for coming to the studio today.
Alexandria Stapleton: Thank you so much for having me.