Diddy remains jailed as judge expresses concern he could send 'coded messages' to employees

• Sean Combs' lawyers argued again in federal court Wednesday that he should be freed pending trial.
• But prosecutors quoted the alleged victims in alleging he tries to threaten and control witnesses.
• The judge said that Combs could send "coded messages" to obstruct justice.

Sean "Diddy" Combs will remain in jail after failing to convince the second federal judge in as many days to accept his $50 million bond package.

US District Judge Andrew Carter, who will oversee the music mogul's criminal trial, cited what federal prosecutors described as Combs' longstanding and ongoing efforts to intimidate witnesses and obstruct justice, including through acts of violence.

"That video is quite disturbing," the judge said at one point, referring to security footage showing Combs beating his then-partner, R&B singer Cassandra "Cassie" Ventura, in a hotel hallway in 2016. Ventura is the main victim identified in the indictment.

Carter's decision may keep Combs confined in a notoriously violent and uncomfortable Brooklyn jail until he takes a plea or goes to trial. Carter has not yet set a trial date.

As he entered the courtroom Wednesday afternoon, Combs appeared to blow a kiss to his family members sitting four rows behind him, then put his hands on his heart.

The record producer appeared to wear the same black T-shirt and striped sweatpants that he wore at Tuesday's hearing, where US Magistrate Judge Robyn Tarnofsky ordered him remanded to jail ahead of trial. On Wednesday, Carter heard Comb's appeal on that decision — but agreed with Tarnofsky that Combs should remain behind bars.

Federal prosecutors in Manhattan have accused Combs of sex-trafficking, illegally transporting people for sex, and running a racketeering conspiracy.

The indictment unsealed Tuesday alleges that for more than a decade Combs planned and ran an elaborate series of "Freak Offs" — highly orchestrated sexual performances, typically held at hotels, at which he used drugs, violence, and threats to coerce women into sexual activity with male commercial sex workers. He assaulted women and threatened to leak videos of the performances to make sure they did what he wanted, prosecutors allege.

Combs has pleaded not guilty to the charges against him.

In arguing for continued detention without bail Wednesday, federal prosecutor Emily Johnson divulged new, more extreme details of the 2016 hotel incident with Ventura, which she said followed a "Freak Off," as well as Combs' alleged intimidation tactics.

According to Johnson, the hotel video was "powerful evidence of trafficking." She said that a commercial sex worker remained in the hotel room as Combs attacked Ventura in the hallway, and noted that Combs dragged her back to the room after beating her.

"'Freak Off' activity is the core of this case, and that activity is inherently dangerous," she said.

According to Johnson, one victim sent text messages to Combs corroborating his assaults, telling him "I have gaping cuts, you hit me in the head two times" and "I'm not a rag doll, I'm someone's child."

Johnson also gave the judge more granular details of Combs' alleged barrage of texts and phone calls to witnesses in the ten months since Ventura went public with many of the same allegations he's now charged with. Combs reached out to victims dozens of times to try to feed them false narratives that they had willingly engaged in consensual sex acts, the prosecutor told the judge.

"There's a massive amount of evidence," she said.

Attorney Marc Angliofo, representing Combs at the hearing, offered a boosted bond package on Wednesday.

In addition to handing over his passport and putting up his $48 million Miami home as collateral, Combs would be under constant surveillance, he said.

In the newly proposed package, Combs would forego the use of his cell phone and the internet, and he would live without any family members in his Miami home. He would also hire the security firm Sage Intelligence to monitor and live with him, and keep a limited list of visitors who would be permitted to enter the building.

But Carter, the judge, was unpersuaded. He said Combs could still try to use the employees at his many companies — possibly by using "coded messages" — to act on his behalf and potentially pressure witnesses.

Angliofo also insisted that the hotel video where Combs assaulted Ventura should be viewed in the context of a consensual — if "toxic" — relationship, and not as part of sex-trafficking.

Bringing a third person into their sexual behavior was "their thing," Angliofo said.

The argument seemed to befuddle the judge, who strained to understand why the example of violence caught on tape — which Combs admitted to and apologized for on social media — should not be an indication that he's a danger to people around him.

"What's love got to do with that?" Carter quipped.

Angliofo also said he spoke to a half-dozen escorts who participated in "Freak Offs." He contended that they all said their experiences were consensual and that they weren't really sex workers.

The people in the agency said "we are not paid to have sex, we are paid for our time," Angliofo said, appearing to quote the conversations. "And if it goes in that direction…"

Johnson, the prosecutor, said the escorts interviewed by prosecutors had very different experiences.

"Half a dozen escorts is just the tip of the iceberg," she said.

Records from the federal Bureau of Prisons show Combs is incarcerated at Brooklyn's Metropolitan Detention Center, a notorious jail that has been home to other high-profile criminal defendants, including Sam Bankman-Fried, R. Kelly, Ghislaine Maxwell, and Michael Cohen.

The criminal investigation into Combs was sparked by a civil lawsuit Ventura filed in November 2023. Combs settled the lawsuit for "an undisclosed and large amount of money," Agnifilo said.

Angifilio stressed at the hearings and in court documents this week that Combs had taken extraordinary measures to cooperate with prosecutors for months.

Combs made a "bad business decision" to pay off the mortgage of his $48 million Miami home so that it could be offered unencumbered as collateral for his proposed bond, he said.

Emails filed to the court show that Combs's lawyers had emailed prosecutors about the singer's travel plans and assured them that he had surrendered his passport so that he would not fly overseas and outside the Justice Department's jurisdiction. Combs' companies have also turned over 144,000 pages of documents over the course of the investigation, Angifilio said.

Prosecutors were unpersuaded by Combs' actions and asked for him to be jailed pending trial, noting he still has "vast resources" at his disposal to help him flee if he wanted to, and alleging that he repeatedly called grand jury witnesses to get them to change their stories about him.

This story has been updated.