Witness: DeLeassa Penland

DeLeassa Penland’s Testimony in Sean 'Diddy' Combs’ Sex Trafficking and Racketeering Trial: Days 24-26 Highlights From June 16 to June 18, 2025, during Days 24 to 26 of Sean 'Diddy' Combs’ federal sex trafficking and racketeering trial at the Daniel Patrick Moynihan U.S. Courthouse in New York, Special Agent DeLeassa Penland of the U.S. Attorney’s Office for the Southern District of New York testified as a prosecution summary witness. Penland, who reviewed evidence but did not directly work on the Combs investigation, presented a detailed timeline of financial transactions, text messages, and videos tied to alleged 'freak-offs'—drug-fueled sexual encounters central to the prosecution’s case. Her testimony aimed to corroborate allegations of racketeering conspiracy and sex trafficking by linking Combs’ business resources to these events, though the defense countered with evidence suggesting consent. Her testimony, spanning three days, was pivotal in organizing hundreds of exhibits for the jury. Penland began on June 16, walking jurors through a chart detailing 'freak-offs' involving Combs, his former girlfriend Casandra 'Cassie' Ventura, and escorts from 2009 to 2017. She highlighted a December 2009 encounter at the London Hotel in New York, where Combs’ American Express paid for an escort named Jules Theodore’s flight from Los Angeles to New York. Text messages shown to jurors included Ventura thanking Combs and coordinating Jules’ travel, with Combs sending an itinerary and pickup instructions. Penland also presented hotel invoices, such as one from October 2012 at the Intercontinental New York, reserved under 'Janet Clark' and paid in cash, alongside another under 'Frank Black' paid partly with Combs’ AmEx, totaling $46,786 in penthouse damages due to baby oil and candle wax use. Other damages included $500 at the Beverly Hills Hotel for drapes and carpets and $950 at the Hermitage Hotel for deep cleaning, suggesting extensive 'freak-off' aftermaths. On June 17, Penland continued, focusing on a March 2016 incident where Combs assaulted Ventura at a Los Angeles hotel, captured on CCTV. She presented a timeline of texts and calls showing Ventura’s outreach to escorts before the incident and Combs’ attempts to contact her afterward, including false claims of impending arrest to manipulate her return. Jurors viewed approximately 20 minutes of 'freak-off' videos from 2012 and 2014, recorded on Ventura’s devices, shown privately with headphones to avoid public exposure. Penland appeared uncomfortable, wincing at one point, as the explicit footage depicted Combs directing sexual encounters with Ventura and escorts. She also read texts from January 2013 where Combs and Ventura planned a 'freak-off' with four men to 'celebrate Christmas,' and October 2013 messages where Ventura coordinated late-night hotel meetups with escorts 'Dave' and Daniel Phillip, asking Combs if he filmed anything. During cross-examination by defense attorney Teny Geragos, Penland faced scrutiny over texts suggesting Ventura’s enthusiastic participation. Messages from October 2012 included Ventura saying, 'I bought the sexiest outfits for later,' and December 2012 texts promising, 'I’ll be the nastiest freak b****.' A role-play text stated, 'The game starts at 10 p.m. no texting after this. I am not Cassie and you are not Sean.' Geragos argued these showed consent, questioning why Penland omitted them from the prosecution’s presentation. Penland clarified her role was to review, not curate, evidence, stating, 'My job was not to add anything to the government’s presentation.' The defense played longer 'freak-off' video excerpts, though details remained private, to reinforce their narrative of a consensual 'swingers’ lifestyle.' On June 18, Penland’s testimony concluded, with further details on Combs’ financial entanglement with 'freak-offs.' She noted Bad Boy Entertainment’s Signature Bank account funded Ventura’s and escorts’ flights, like a 2010 trip, and Kristina Khorram’s 2016 efforts to suppress the hotel assault video. On redirect, prosecutor Emily Johnson emphasized the harm Ventura allegedly suffered, reinforcing the coercion narrative despite the defense’s texts. Penland’s testimony, while technical, tied financial records, texts, and videos to witness accounts, supporting the prosecution’s claim of a criminal enterprise. However, the defense’s cross-examination highlighted Ventura’s apparent agency, leaving jurors to weigh consent versus coercion. Legal analysts noted Penland’s evidence strengthened the prosecution’s case but required further proof of criminal intent to secure convictions.

Compiled from news sources and summarized by Grok.

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