Kimmel wonders – During a Wednesday monologue on “Jimmy Kimmel Live!,” Jimmy Kimmel joked about Sean “Diddy” Combs’ moved-up prison release date and wondered if it would happen before the release of the Epstein files.
Jimmy Kimmel didn’t waste time Wednesday night—right off his “Jimmy Kimmel Live!” monologue, he zeroed in on the latest update to Sean “Diddy” Combs’ prison timeline and threw in a question that immediately pulled in the darker shadow hovering over the news cycle.
Kimmel speculated that the rapper could be out before all of the Epstein files finally drop. He made the comment after briefly addressing another headline: the Iran war deal. With a joke. he suggested the military operation had successfully “take our attention away from the Trump-Epstein files. ” before adding. “But don’t worry. the second it is really over. Oh, we’re getting right back into that.”.
Then came the line that landed hardest: “I wonder which gets released first, the rest of those files or Diddy?”
Kimmel followed with the prison update itself. He said Combs was now set to be released from prison in February 2028. Kimmel described Combs as serving time at Fort Dix in New Jersey for “extracurricular activities.” He noted that Combs’ release date had already moved up—first from June 2028 to April. and then again to February 2028. which Kimmel said is “almost in time for Valentine’s Day.”.
Kimmel also voiced doubt about whether Combs would actually want that kind of timing. saying the rapper “just miss” the romantic holiday and then connecting it to the pressure of ongoing legal troubles. He added that Combs is “reportedly still facing upwards of 70 civil lawsuits across the country. ” before joking. “I know if I was facing 70 lawsuits. I’d just stay in prison.”.
Right before shifting away from the subject, Kimmel tossed in one last jab at how quickly attention can change, saying, “between Diddy’s release and the Strait of Hormuz opening, the oil is going to be flowing like never before.”
Kimmel’s monologue aired on Wednesday as part of “Jimmy Kimmel Live!,” which airs weeknights at 11:35 p.m. ET on ABC. His full monologue is available via the embedded video.
Jimmy Kimmel Diddy Sean Combs Fort Dix Epstein files Trump-Epstein files Valentine’s Day Iran war deal Strait of Hormuz civil lawsuits