The 4 most shocking moments in Netflix’s Diddy docuseries, broken down by director Alexandra Stapleton

• "Sean Combs: The Reckoning" features interviews and footage of Diddy days before he was arrested.
• Director Alexandra Stapleton spoke to BI about the docuseries' most shocking moments.
• They include a sex worker's recollection and a chilling revelation from singer Aubrey O'Day.

"Sean Combs: The Reckoning" shows a side of Diddy we've never seen before.

Netflix's four-part docuseries chronicles the rise and fall of Combs, also known as Diddy, as he goes from hip-hop mogul and billionaire business owner to the subject of a federal prosecution and over 60 civil lawsuits accusing him of sexual abuse.

Combs, who pleaded not guilty, was ultimately convicted on two counts of transportation to engage in prostitution and is serving a 50-month prison sentence. He was acquitted of the most serious charges, including RICO conspiracy and sex trafficking by force or fraud, and is set to be released in May 2028. Combs has denied all wrongdoing in the civil cases.

Not only does the series feature interviews with many who have been inside Diddy's inner circle, including Bad Boy Records cofounder Kirk Burrowes, actor Mark Curry, singer Aubrey O'Day, and one of the sex workers who engaged in Diddy's now-infamous freak offs, but it also includes never-before-seen footage of Combs in the days leading up to his arrest.

The inclusion of the latter has already made waves in the press and infuriated Combs and his team. They've also broadly disputed the allegations presented in the documentary.

"Netflix's so-called 'documentary' is a shameful hit piece," Combs' spokesperson Juda Engelmayer told Business Insider. "Netflix relied on stolen footage that was never authorized for release. If Netflix cared about truth or about Mr. Combs's legal rights, it would not be ripping private footage out of context — including conversations with his lawyers that were never intended for public viewing."

Netflix declined to comment.

"Sean Combs: The Reckoning" director Alexandra Stapleton told Business Insider that she obtained the footage legally, although she wouldn't disclose the details of how it was acquired when asked.

The director — whose previous documentary titles include 2023's "Reggie," on baseball legend Reggie Jackson and 2024's "How Music Got Free" on tech changing the music industry — had been developing the project ever since Combs' former girlfriend Cassandra Ventura, a singer under the name Cassie, accused him of rape and a "cycle of abuse" in a November 2023 lawsuit.

Though the case was quickly settled for $20 million, it opened the floodgates for a wave of misconduct suits against Combs and Ventura; Ventura would later testify against Combs in his federal trial.

Stapleton quickly found an ally in another hip-hop heavyweight, Curtis "50 Cent" Jackson, whom she featured in "How Music Got Free." The rapper and business mogul, who has feuded with Combs for years, is an executive producer.

Combs' team has said his involvement is due to his feud.

"I definitely knew that there were things that 50 could bring to the table that would be immensely useful to me for access," Stapleton told Business Insider.

The doc offers plenty of revelations via footage and interviews. Below, Stapleton offers insight into the most shocking moments.

Never-before-seen footage shows Diddy's final days before being arrested

Throughout the doc's four episodes, footage from a videographer hired by Combs shows him in the days leading up to his arrest.

Stapleton, who told Business Insider that the footage was acquired "completely legally," said that she had hoped to obtain an interview with Combs.

"I made that very clear behind the scenes that that was a really big goal to get him to sit down and talk, but it never materialized," she said.

In the doc, Combs is in New York City to cooperate with authorities. The footage shows him plotting out the best way to spin the negative press. "We're losing," he says on a call with his team while sitting in his hotel room.

Later in the docuseries, Combs spends an evening in Harlem, where he takes pictures with fans and even accepts a jacket given to him by a supporter. Afterward, while in his SUV, he asks for hand sanitizer and says he needs to take a bath.

"The amount of people that actually I'm coming in contact with, that's what I have to do," he said. "It's time to cleanse, I gotta go under the water, water gotta be boiling hot, put some peroxide in that."

The Bad Boy Records cofounder said Diddy figured out a way for Biggie Smalls to pay for his own funeral

The docuseries doesn't focus exclusively on the last few years of Combs' life. It also delves into his past, specifically the East Coast/West Coast rap rivalry in the mid-1990s that resulted in the murders of Tupac Shakur and Combs' friend, The Notorious B.I.G., also known as Biggie Smalls.

Bad Boy Records cofounder Kirk Burrowes recalls in the docuseries Combs' proclamation that he was going to throw the "biggest funeral for Biggie New York has ever seen." However, Burrowes said, when Combs crunched the numbers, he realized he didn't want to foot the bill himself — so he made the funeral a recoupable charge to Biggie Smalls, so the rapper's estate would bear the financial burden.

Stapleton said it was important to feature people from Combs' past, such as Burrowes, to illustrate how Combs has operated.

"What's interesting about Kirk Burrowes is that his allegations go way back in time," she said. "A lot of what he talked about goes all the way back to the early 2000s, so we really thought it was important to include that part."

Combs, Burrowes, and Biggie Smalls' estate did not respond to a request for comment.

A sex worker describes what his freak offs with Diddy and Cassie entailed

One of the most shocking elements of the indictment was the detailed sex performances Combs allegedly arranged between female victims and male sex workers, which Combs called "Freak Offs."

In the docuseries, one of those sex workers, Clayton Howard, steps forward to talk about his yearslong encounters with Diddy and Combs' then-girlfriend Ventura. The two dated for over a decade, breaking up in 2018.

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 says in the docuseries of his first encounter with Ventura.

Howard gives detailed recollections of his sexual encounters with Ventura that included baby oil and instances where Ventura collected Howard's semen, all of which were "heavily regulated" by Combs. Howard said that on the anniversary of the murder of The Notorious B.I.G., the couple would fly him in to party and have sex with Ventura over multiple days. Howard said his sexual encounters with Ventura went on for eight years.

"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," Stapleton 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.'"

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

"I'm glad I told the truth, regardless if the world chooses to accept it. The trial exposed enough that those who paid attention know I spoke the truth," Clayton said. "Mr. Combs was guilty, but so was Cassie, and domestic violence does not erase conscious decisions made by her to please her lover."

Ventura did not respond to a request for comment.

Previously, Business Insider reported that Ventura felt pressured into participating. "I was just in love and wanted to make him happy," Ventura testified at Combs' May trial.

"I felt pretty horrible about myself. I felt disgusting. I was humiliated. I didn't have the words at the time to tell him how I felt," Ventura added on the stand. "And I couldn't talk to anyone about it."

Aubrey O'Day says she has no recollection of a possible sexual assault by Diddy

One of the most chilling moments in the docuseries is when singer Aubrey O'Day reads an affidavit from a woman who said she witnessed Combs and another man sexually assaulting O'Day, though O'Day said she has no recollection of this.

Earlier in the docuseries, O'Day, a former member of the girl group Danity Kane, which was formed by Combs for the 2005 MTV series "Making the Band," reads an email Combs sent to her in 2008, the year she was fired from the group.

In it, he says, "I don't wanna just fuck you. I want to turn you out." He ends the email by saying he's going to finish masturbating while watching porn and thinking of her.

Later in the docuseries, O'Day reads an affidavit from one of the civil lawsuits of an alleged Combs victim. It states that this woman witnessed O'Day in 2005 being sexually assaulted by Combs and another man.

While opening doors looking for the restroom, the woman said she opened one door to find Combs and the other man in sexual acts with O'Day, who was "sprawled out on a leather couch, looking very inebriated." The woman wrote in the affidavit that she is "100% certain" that the person was O'Day.

"Does this mean I was raped?" O'Day says in the docuseries. "I don't even know if I was raped, and I don't want to know."

"Aubrey's contribution and her stories are really very, very complicated and a symbol of the gray area of a lot of this," Stapleton said. "It was very raw for her. It was really deep for her, and it took a lot of conversations for her to feel like, 'I want to be public about this.'"

"It was never about not sharing it; it was more potentially, 'How do I present to the world that this isn't a binary feeling that I have? That I'm not going to sit here and say yes, this is absolutely true when I don't know if it's true, and also be like this is total BS when part of me feels what if it is true?'" Stapleton said. "Aubrey, in real time, was trying to figure out."

O'Day did not respond to a request for comment.

"Sean Combs: The Reckoning" is streaming now on Netflix.