Shocking Revelations From 'Sean Combs: The Reckoning' Doc That Will Leave You Speechless

Footage captures Diddy's anxiety before arrest, co-founder recalls intimidation tactics
Sex worker recounts years of 'Freak Offs' with Diddy and ex-girlfriend Cassie
Aubrey O'Day alleges sexual advances, claims she was assaulted by Diddy

"Sean Combs: The Reckoning", Netflix, Diddy, — Source: Netflix / Netflix

The internet is abuzz over the explosive Netflix docuseries Sean Combs: The Reckoning, executive-produced by Curtis “50 Cent” Jackson and directed by Alexandria Stapleton. The series delves into the complicated life of Sean “Diddy” Combs and the events that culminated in his 2025 trial and conviction on two prostitution-related charges under the Mann Act.

Here are some of the most shocking revelations from the docuseries.

1. Never-before-seen footage captures Diddy in the days leading up to his arrest in Sean Combs: The Reckoning.

Across the docuseries’ four episodes, footage shot by a videographer hired by Sean Combs offers a rare look at him in the days before his arrest. In one scene featured in episode one of the docuseries, a frustrated and worried-looking Diddy can be seen speaking to his attorney from a hotel room, nervous about the outcome of the trial.

“Things are happening, and it’s like — I want to fight for my life. I want to fight for justice,[for] not guilty. I want to have a life to be able to live,” he tells his attorney, Marc Agnifilo. “It’s really going to be hard for me to take more hits than I’ve taken, and — god forbid — get in front of a jury and have a chance.”

Agnifilo reassures the hip-hop star that everything will be okay, replying, “You didn’t do anything wrong…You’ve handled this with complete honor.”

But Diddy quickly retorts, “I don’t think it’s working. We’re losing.”

Stapleton told Business Insider on Dec. 2 that the footage was obtained “completely legally,” and said she had hoped to secure an interview with Combs.

2. Bad Boy Records co-founder Kirk Burriws recalls disrespect and intimidation

Bad Boy Records co-founder Kirk Burrowes helped Diddy build Bad Boy Records from the ground up upon its 1993 inception, managing accounts and the company’s finances, but as the label grew, Burrowes began to see an ugly side of Diddy emerge.

In episode two of the docuseries, Burrowes recounted a day when Diddy allegedly entered the office carrying a baseball bat and a suitcase containing the label’s stock, and “threatened” him to give up his 24% stake in the company.

“He wants the stock back. He wants it now,” Burrowes recalled in the documentary. Diddy reportedly claimed he needed the money for a business deal and promised to return the stock.

Reflecting on why he ultimately surrendered his shares, Burrowes said:

“I didn’t want to give it back. I wanted to stay in good graces. I still wanted to be at the company.”

Burrowes filed a lawsuit against Diddy in 2003 for breach of contract and fraud, but the case was dismissed because the court found it had been filed too late. Burrowes filed another suit against Diddy in 2025, alleging years of “predatory” actions toward him, which remains pending, according to Netflix.

The docuseries also revisits Diddy’s involvement in the infamous East Coast/West Coast rap feud of the mid-1990s that led to the deaths of Tupac Shakur and Combs’ friend and artist, Biggie Smalls, AKA The Notorious B.I.G. Burrowes recalled Combs declaring that he intended to throw the “biggest funeral for Biggie New York has ever seen.” However, he explained that after Combs calculated the cost, he decided not to cover it personally and instead made it a recoupable expense for Biggie Smalls’ estate.

“Sean doing a big show looks good on him, but he’s not going to tell the world that Biggie’s gonna pay for it,” Burrowes said toward the end of the episode.

3. Sex worker recounts “Freak Offs” with Combs and Cassie

One of the most shocking elements of the indictment involves the so-called “Freak Offs,” sexual performances that Combs allegedly arranged between female victims and male sex workers. In the docuseries, one of these sex workers, Clayton Howard, speaks about his years-long encounters with Combs and his then-girlfriend Ventura, who dated Combs for over a decade before their 2018 breakup. Howard said he was first hired by Ventura and Combs in 2009.

“She tells me that I’m there to please her for her husband, they’re married, they like to spice things up,” Howard recalled in the docuseries, according to Business Insider.

Howard provided detailed accounts of sexual encounters with Ventura involving baby oil and instances where she collected his semen, all reportedly “heavily regulated” by Combs. On anniversaries of The Notorious B.I.G.’s murder, he said he was flown in to party and engage in sexual activity with Ventura over several days. His encounters reportedly continued for eight years.

Explaining Howard’s decision to participate in the docuseries, Stapleton explained to Business Insider:

“I think Clayton was pretty comfortable coming forward with his story because he wanted to own his narrative. He was kind of brought out of the woodwork as a result of Cassie’s lawsuit,” she said. “I think once it became very public, Clayton’s position was, ‘I’m a human being, I lived through this a number of years, and I want to share my story.'”

Howard told Business Insider that he has no regrets about participating in the docuseries.

4. Aubrey O’Day speaks out about Diddy’s alleged sexual advances and reveals an explosive affidavit claiming the mogul assaulted her.

Aubrey O’Day — who was selected to join Danity Kane on Season 3 of Diddy’s Making the Band in 2005— appears in the third and fourth episodes, where she detailed the mistreatment she suffered while working with the Bad Boy label exec. Now 41, she recalled being singled out early on, with Diddy making inappropriate comments about her appearance.

“Diddy made it clear that I was ‘the looker,’” O’Day said in episode three, according to Variety. “I remember that phrase a lot. He was separating me and there was a different set of expectations from me, and I just naturally float into the grooming.”

Danity Kane’s self-titled debut album arrived in 2006, earning major commercial success in the U.S. with one million copies shipped and producing two hit singles—the top-10 track “Show Stopper” and the ballad “Ride for You.” Their follow-up album, Welcome to the Dollhouse, was released in 2008 after the group scored another top-10 single with “Damaged.” With these back-to-back No. 1 debuts, Danity Kane became the first female group in history to see their first two albums enter the Billboard 200 chart at No. 1.

However, internal tensions eventually surfaced, culminating in the October 2008 season finale of Making the Band 4, where Diddy dismissed Aubrey O’Day and D. Woods (Woodgett) from the group.

In the documentary, O’Day said she believed she was booted from the group because she declined Diddy’s sexual advances over the years. The singer claimed he “crossed the line” during their time working together, including one incident where he sent “emails with pictures of his penis.” Reading one of the alleged emails aloud for the camera, one passage read:

“‘I don’t wanna just fu-k you. I wanna turn you out. I can see you being with some motherfucker that you tell what to do. I make my woman do what I tell her to do, and she loves it. I just want — and like — to do things different. I’mma finish watching this porn and finish masturbating. I’ll think of you, happy face. If you change your mind and get ready to do what I say, hit me. Happy face. God bless, Diddy. God is the greatest.”

Reacting to the shocking message, O’Day told the camera:

“This is your boss at your work sending you that e-mail. What happens in real life to anyone else? Your boss gets fired. Six months later, I was fired. I absolutely felt that I was fired for not participating sexually, but I also found out later that [fellow Danity Kane member] Dawn [Richard] and Puff were recording a different project. I was the star of the show, and Puff needed to move that entire audience over to a new project.”

In the final episode, O’Day revealed another shocking story. She claimed she received an affidavit from a woman who alleged that she accidentally walked into a room where O’Day was “sprawled out on a leather couch, looking very inebriated,” Variety reported. The incident allegedly happened in 2005, according to USA TODAY. The woman claimed she was looking for the bathroom when she allegedly walked in on O’Day “naked from the bottom half,” allegedly being sexually assaulted by Diddy.

“Puff Daddy was penetrating in her vagina, and there was another stalky light-skinned man with his penis in her mouth,” O’Day revealed while reading the affidavit on camera.

The singer became emotional as she claimed she had no recollection of the incident.

“I didn’t drink like that at all — I don’t drink at all, it’s never been an issue with me,” she said in the Netflix doc. “Does this mean I was raped?” O’Day asked. “Is that what this means? I don’t even know if I was raped, and I don’t want to know. I don’t want to find out any more that that woman has to say. If she made it up, I would be compelled to take her the fu-k down. You realize the burden that that puts on my soul for the past year, which is if I expose one victim who’s got a civil lawsuit, that gives Diddy and his legal team credit to take down everybody else as potential liars…It goes right back on my shoulders, just like that. The weight of that man and his bullsh-t … I will never get up from under it.”

Have you seen Sean Combs: The Reckoning on Netflix? Thoughts?