Sean ‘Diddy’ Combs Asks for Bail Again

Sean “Diddy” Combs appeared in court on November 22 to once again push for release in his Manhattan federal sex-trafficking case — a request already shot down by two other judges and an appeals court judge while the 2nd U.S. Circuit Court of Appeals considers his bail request. When Combs entered the courtroom just after 2 p.m., he looked at his family in the gallery, blowing kisses and tapping his heart. Combs entered the courtroom unshackled. He sported a khaki jail uniform — button-down top, with a long-sleeved thermal underneath, and relaxed-fit pants — and embraced his attorneys before taking his seat at the defense table. Combs donned glasses as he looked over documents for several moments before the proceeding took off. Combs appeared attentive throughout the hearing. At various points, Combs sat with his arms crossed or sometimes on his lap. He took a sip of water at least once. 

Judge Arun Subramanian said that he would make his decision on bail next week, while the proceedings dished out more examples of Combs’s alleged bad-boy behavior behind bars. Prosecutors hammered him for breaking rules in jail, saying if Combs can’t be trusted in lockup, then he certainly can’t be trusted out on bail — no matter what measures were taken to keep the rapper in check. Combs’s lead attorney, Marc Agnifilo, said he understood that home detention at Combs’s South Florida home — which is on an island, with a boat dock — would be a hard sell. Instead, they had found a three-bedroom apartment on the Upper East Side for Combs, where he could stay, along with three full-time security staff, if released. Combs’s bail proposal also included a $50 million bond, backed by his $48 million Star Island estate. 

“For conditions to be sufficient, there has to be some level of trust that the defendant will follow them, and the defendant here has demonstrated either he cannot or he will not follow rules,” prosecutor Christy Slavik told Subramanian. “The defendant, simply put, cannot be trusted — he’s left no doubt that he cannot comply with conditions.” Slavik said that Combs’s lawyers couldn’t control him — and that his pitch for 24/7 monitoring by private security, that he himself would bankroll, fell flat. “The defendant has continued to communicate through unauthorized channels at [jail], and he has continued to communicate through unauthorized channels through his attorneys,” she said. “His attorneys are effectively enabling his flouting of [jail] rules.” 

Combs was alledly engaging in inappropriate efforts to sway would-be jurors’ views of the case, including with his press strategy. “What we have here is the defendant’s concerted effort to affect the integrity of these proceedings,” Slavik said. Combs himself told familiars that he wanted this, she alleged. “He is saying, ‘I want to “reach for this jury, I just need one,”’ and it’s with that intent that he’s proceeding with these PR campaigns.” 

Slavik also fought Combs’s efforts to downplay the video showing him attacking former girlfriend Casandra “Cassie” Ventura in a hotel nearly a decade ago; she’s been referred to as Victim-1 in court proceedings. Combs’s camp has complained that the video presented to court — which has been used by prosecutors in pushing for his detention — was edited by CNN to play out of order. 

“It was a bit puzzling that the defendant brought this up, because there’s really no dispute as to what actually happened during that incident. In fact, the defendant admitted to it and apologized for it in a public Instagram post,” Slavik said. “Whether the video was slowed or spliced or edited by CNN, there’s really no dispute about what the video shows — it shows the defendant shoving, kicking, and dragging a female victim.” 

When making his pitch for bail, Agnifilo insisted there was context behind the video that undermines its being used as proof of violent proclivities. “It really is purely consistent with our view of this being a consensual, long-term, loving, fraught relationship that had a breakup, and the breakup wasn’t because of coerced sex or forced sex,” he argued. 

Combs was arrested on September 16 following numerous allegations of sexual misconduct. The indictment details a shocking history of alleged abuse over the course of “decades” and charges him with racketeering conspiracy; sex trafficking by force, fraud, or coercion; and transportation to engage in prostitution. The Manhattan U.S. Attorney’s Office alleged that Combs “abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct.” Combs, with the help of his employees, used his business empire to craft a “criminal enterprise,” according to federal prosecutors.

The Feds contended that Combs verbally, emotionally, physically, and sexually abused women and others for years — and that he “manipulated women to participate in highly orchestrated performance of sexual activity with male commercial sex workers.” Civil lawsuits against Combs also allege abuse against men and boys. As for the women under his control, Combs maintained his authority by drugging them, threatening their careers, and abusing his financial power over them, prosecutors alleged.

Combs used his criminal enterprise to draw women into his troubling world, frequently under the guise of a romantic relationship, and then force them to participate in what he referred to as “freak offs,” prosecutors said. These freak offs, the Feds claimed, “were elaborate and produced sex performances that Combs arranged, directed, masturbated during, and often electronically recorded.” These were allegedly frequent and sometimes lasted multiple days. After the freak offs concluded, Combs and his victims “typically received IV fluids to recover from the physical exertion and drug use,” prosecutors said. During a raid in March, prosecutors said, authorities found drugs and “more than 1,000 bottles of baby oil and lubricant.” Male sex workers were purportedly at the core of the freak offs. The Feds claim that Combs used force and threats to pressure his victims to engage in “extended sex acts with male commercial sex workers,” according to the indictment. Combs has pleaded not guilty to the charges. 

Since Subramanian said he would issue a decision on bail next week, Combs will spend at least another weekend in jail and, in all likelihood, probably won’t be released before trial in May 2025. As Combs was escorted out of court, he offered his family gushy good-byes — the same kisses and waves with which he made his entrance.