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Sean ‘Diddy’ Combs is set to be sentenced and faces the possibility of years in prison

October 3, 2025 by Chicago Tribune

NEW YORK — Sean “Diddy” Combs faces sentencing Friday in a sordid criminal case that could keep him locked up for years.

The hip-hop mogul was convicted in July of flying people around the country for sexual encounters, including his girlfriends and male sex workers, in violation of the federal Mann Act.

A jury acquitted Combs, 55, of more serious racketeering conspiracy and sex trafficking charges that could have put him away for life.

Prosecutors say he should spend more than 11 years in prison for his conviction on two counts of transportation to engage in prostitution. Combs’ lawyers want him freed now, saying the long sentence sought by prosecutors is “wildly out of proportion” to the crime.

U.S. District Judge Arun Subramanian, who will decide the sentence, has signaled that Combs is unlikely to be freed soon. He twice rejected bail for the rapper, who has been jailed at a federal detention center in Brooklyn since his arrest a year ago.

The sentencing comes after a nearly two-month trial featuring testimony from women who described being beaten, threatened, sexually assaulted and blackmailed by Combs.

A former girlfriend, R&B singer Casandra “Cassie” Ventura, said Combs ordered her to have “disgusting” sex with strangers hundreds of times during their decade-long relationship.

The jury was repeatedly shown video clips of Combs dragging and beating Cassie in a Los Angeles hotel hallway after one of those multiday sexual marathons, which she referred to as “freak-offs” during her four days of testimony.

A woman who testified under the pseudonym “Jane” told jurors she too was subjected to violence and felt obligated to perform sexually with male sex workers at drug-fueled “hotel nights” while Combs watched and sometimes filmed.

To support their racketeering case, prosecutors also brought on witnesses who testified about other violent acts. A former personal assistant testified that Combs raped her. One of Cassie’s friends told the jury Combs dangled her from a 17th floor balcony. The rapper Kid Cudi testified that Combs broke into his home after learning he and Cassie were dating.

Although the jury acquitted Combs of racketeering, the judge can still consider that testimony as he decides the sentence.

Subramanian is also considering letters submitted by Combs and some of his accusers.

In his letter to the judge Thursday, Combs promised he would never commit another crime if released, saying, “The old me died in jail and a new version of me was reborn.”

In her letter, Cassie called Combs a manipulative abuser who has “no interest in changing or becoming better.”

“He will always be the same cruel, power-hungry, manipulative man that he is,” she wrote.

A former personal assistant who said Combs raped her in 2010 asked Subramanian to deliver a sentence “that takes into account the ongoing danger my abuser poses to me, and to others.” The former assistant, who testified under the pseudonym “Mia,” is expected to speak at Friday’s sentencing.

Combs will address the court, according to court filings. His defense team is also planning to play a roughly 11-minute video.

Combs’ lawyers say the sexual encounters were consensual and that being in jail has hastened Combs’ sobriety and forced him to learn from his misbehavior. They have said there is no need for him to remain behind bars because he has already been punished enough.

At a court hearing last week, Combs seemed buoyant, as he told his mother and children that he is “getting closer to going home.”

Filed Under: White Sox

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