Diddy Or Didn’t He – Trial Day 27 Recap

Judge Calls Break After Jury Watches Diddy’s Homemade Porn

The jurors got more than an eyeful on Day 27 of the Sean “Diddy” Combs federal trial, sitting through nearly 45 minutes of explicit sex tapes—most filmed by Diddy himself. Homeland Security agent Joe Sirchillo returned to walk them through a dizzying array of charts, timelines, escort invoices, and freak-off logistics, all tied to a sprawling racketeering case that’s nearing its end.

Courtroom observers were barred from viewing the tapes, but jurors watched clips featuring a woman identified as Jane across multiple dates in 2021 and 2022. Sirchillo laid out how Diddy coordinated these sessions with male escorts, used hotel suites in different cities, and even argued about a $600 refund over an underperforming sex worker. It wasn’t just smut on screen—it was smut with metadata and receipts.

The defense countered with their own batch of videos and texts suggesting Jane was a willing participant, even initiating sexual scenarios and asking for $15,000 in shopping money. Diddy sent it. At the heart of the battle now is whether these actions were personal or part of a criminal enterprise run through Bad Boy Entertainment.

Closing arguments are expected Thursday and Friday, and both sides are prepping for a four-hour legal showdown. With court dark on Wednesday, Day 28 will bring more cross-examination of Agent Sirchillo—and possibly more screens and squirming.