Tuesday was Day 25 of Sean “Diddy” Combs’ federal sex trafficking and racketeering trial, and it wasn’t that again short on jaw-dropping moments, although it also wasn’t just the aim of at least some of the prosecutors to drop jaws. The mood in the courtroom did a complete 180 on Tuesday (June 17) when Diddy’s defense team began pulling back the curtain on the duo’s relationship with saucy, unfiltered text message conversations that contributed to an unexpectedly steamy image of the hip-hop mogul’s on-again, off-again relationship with his ex, Cassie Ventura.
Fronting the fight was Diddy’s lawyer, Teny Geragos, who waged a war of words on the prosecution narrative by flagging what seemed like consensual, even enthusiastic, back-and-forth between Cassie and Diddy. In one especially frank message from August 2009, Cassie was to the point when Diddy asked when she wanted to “freak off.” Her reply? “I’m always ready to freak off, but that was only the beginning.
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Another missive found Cassie proclaiming, “I’m so horny I can’t think straight,” before telling Diddy to pack an overnight bag, a steamy warning indeed, on their way to Duane Reade. That message did not appear to be on the prosecution’s evidence list. Geragos and the defense reminded the court of that during the testimony of U.S. Attorney’s Office special agent DeLeassa Penland.
But it wasn’t just Cassie’s text messages that elicited gasps. Male prostitute Jules Theodore became a person of interest in the court spotlight, allegedly telling Diddy that he needed a “sleep” with “you guys are rabbits LOL.” The word “rabbits,” evidence showed, was a term used to refer to the couple’s frequency and intensity of their sexual relations, sometimes for hours at a time or days on end.
Throughout the trial, Geragos was intent on proving that Cassie was a willing participant in many of the sexual acts she later described as abusive in some cases, even the person initiating them. One message had Cassie admitting to being “horny and bored,” and another spoke of having “sexy flashbacks of yesterday.” She went so far as to offer to reward him for a previously missed date by being “the nastier freak b####.”
Of all the times we’ve seen them talk or retreat into silence, perhaps the most personal came in a Father’s Day message: “I can’t wait until we have a baby,” Cassie wrote, and then added, “I wish we could have freaked out before you left.” Geragos employed this sentiment to continue attacking the prosecution’s depiction of Diddy as a slimy, violent character, painting the messages as an exchange of mutual interest, even longing.
Whether these revelations have further complicated the prosecution’s case or added another layer of drama to an already sensational trial is open for debate. Now that the line between affection and alleged abuse is on trial, the court has its work cut out to decide where to draw the line. The trial continues Wednesday (June 18), and if Tuesday’s testimony is any indication, it will only get hotter.
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