Sean ‘Diddy’ Combs’ Time in Jail Is ‘Beginning to Wear on Him’ 3 Months After Arrest

Sean “Diddy” Combs appeared in a court hearing regarding his sex trafficking case on Wednesday, December 18, and an eyewitness claimed it looked like jail was “beginning to wear on him.”

“A lot different from the luxury lifestyle that he was living before, but he appeared very noticeably thinner and maybe being locked up in detention is starting to wear on him,” reporter Elizabeth Millner said during a Law & Crime livestream held outside the federal courthouse in Manhattan, noting his hair was a “little bit” greyer.

Diddy has been denied bail three times since his arrest on September 16. The disgraced rapper was most recently denied bail on November 27, leading Judge Arun Subramanian to further explain that “no condition or combination of conditions will reasonably assure the safety of the community.”

“There is compelling evidence of Combs’ propensity for violence,” the federal judge said, per ABC 6.

Diddy will remain behind bars until his trial begins in May 2025.

The Bad Boy Records founder spent his first holiday in jail on Thanksgiving and was offered a special meal in celebration. In Touch viewed a copy of the menu at the time and reported that the Making the Band alum enjoyed cereal, fruit, breakfast pastries and skim milk, for breakfast at 6 a.m. For lunch, Diddy chose between roast turkey or hot and sour tofu for his main course, accompanied by mashed potatoes, cranberry sauce, mixed vegetables, turkey gravy and dinner rolls. Special beverages and pies wrapped up the meal.

Earlier that month, Diddy turned 55 behind bars and celebrated his birthday during a phone call with his kids Christian Combs, Quincy Jones, Chance Combs, Justin Combs, Love Combs, and twins Jessie Combs and D’Lila Combs.

“I can’t wait to see y’all. And I just want to say I’m proud of y’all … just for being strong. Thank you for your strongness. Thank you for being by my side,” Diddy said to his kids over the phone, seen in a video via Instagram shared by Justin.

Diddy’s September arrest came nearly one year after his ex Casandra “Cassie” Ventura filed a lawsuit against him for sex trafficking and sexual assault.

“Throughout their relationship Mr. Combs was prone to uncontrollable rage, and frequently beat Ms. Ventura savagely. These beatings were witnessed by Mr. Combs’ staff and employees of Bad Boy Entertainment and Mr. Combs’s related businesses, but no one dared to speak up against their frightening and ferocious boss,” the court November 16, 2023, statement in the filing read.

Diddy denied all allegations made against him. However, he settled the lawsuit one day later.

The Get Him to the Greek actor got in trouble with the law months later when Homeland Security raided Diddy’s Los Angeles and Miami properties in March. The entertainer wasn’t at either home during the incident, however, he was arrested by Homeland Security in September on racketeering conspiracy, sex trafficking by force, fraud or coercion, and transportation to engage in prostitution charges. He pled not guilty to the charges in a court hearing on September 18.

Following Diddy’s arrest, more alleged victims stepped forward and filed sexual harassment lawsuits against him. He has continued to defend his innocence.