Jury Reviews Cassie Messages as Prosecutors Near Close in Diddy Trial

Here we go, on Day 27 of Sean “Diddy” Combs’s federal trial in Manhattan, courtroom focus sharpened on intimate messages exchanged between Combs and his former girlfriend Cassie Ventura. With jurors back after a sick day break and Juneteenth—testimony resumed this morning featuring key evidence from insiders.

Get this, Brendan Paul, who previously served as one of Diddy’s personal assistants, described a grueling work environment. He testified he once worked three straight days with barely any sleep and was ordered to purchase significant quantities of drugs. Paul added that Combs treated his inner circle like a “U.S. military’s SEAL Team 6,” accepting no refusal.

Under intense cross‑examination by defense attorney Brian Steel, Paul conceded that “Jane,” the pseudonymous alleged victim, never appeared reluctant during what prosecutors refer to as “freak offs.” He stated, “Jane appeared to be a willing participant in the sexual encounters,” directly contradicting earlier testimony that claimed non‑consensual behavior.

Prosecutors also highlighted text messages from Cassie to Combs. In one exchange, Cassie wrote, “That’s not love, that’s possession,” referencing the alleged 2016 hotel incident in which she says she was assaulted . Defense attorneys used evidence of a March 2017 text in which Cassie wrote, “I love our FO’s when we both want it,” suggesting consensual dynamics in their intimate encounters .

The government aims to rest its case on Monday after presenting thirty‑four witnesses over the past six weeks. In contrast, Diddy’s legal team indicated they would require around two days to present their defense, positioning closing arguments for Thursday.

For those tracking the trial nightly, NBC’s Dateline is releasing special episodes of “True Crime Weekly” alongside on‑site commentary from correspondent Andrea Canning and Chloe Melas.