After Diddy’s prison release date moved up again, Jimmy Kimmel speculated that the rapper might be out before all of the Epstein files finally drop.
The late night host addressed Diddy’s prison update during Wednesday’s monologue for “Jimmy Kimmel Live!,” where he noted that the embattled Bad Boy Records founder was now set to be released from prison in February 2028.
Though, before touching on Diddy’s news, Kimmel did address the Iran war deal, joking the military operation did successfully “take our attention away from the Trump-Epstein files.”
“But don’t worry, the second it is really over. Oh, we’re getting right back into that,” Kimmel said. “I wonder which gets released first, the rest of those files or Diddy?”
He continued: “You know, Sean ‘Diddy’ Combs got his release date moved up again. He’s doing time right now at Fort Dix in New Jersey for his extracurricular activities. He was scheduled to get out in June of 2028. That was moved up to April. And now he’ll be released in February of 2028, which is almost in time for Valentine’s Day.”
Though, Kimmel noted that Diddy will “just miss” the romantic holiday, pondering whether the rapper actually wants to get out of prison due to his many civil lawsuits.
“Diddy is reportedly still facing upwards of 70 civil lawsuits across the country,” Kimmel added. “I know if I was facing 70 lawsuits, I’d just stay in prison.”
Before moving on to another topic, Kimmel cracked that “between Diddy’s release and the Strait of Hormuz opening, the oil is going to be flowing like never before.”
Watch Kimmel’s full monologue above.
“Jimmy Kimmel Live!” airs weeknights at 11:35 p.m. ET on ABC.

