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Diddy Allegedly Sent His Staffers to Win Back J.Lo

1999 MTV Music Awards Arrivals
Photo: Jeff Kravitz/FilmMagic, Inc

In the six months since Cassie accused producer Sean “P. Diddy” Combs of physically and sexually abusing her throughout their 11-year relationship, her lawsuit has set off a wave of horrific allegations. On Tuesday, Rolling Stone added more to the list, including accounts from former Howard University students who say they saw Combs beat his then girlfriend with a belt while at the university and reports that he broke a chair over the head of the late music executive Shakir Stewart after Stewart started dating Combs’s ex Kim Porter. The investigation also outlines a disturbing detail from the aftermath of his relationship with Jennifer Lopez: According to a former intern at Diddy’s record label, Bad Boy, the producer tried to win back J.Lo after their breakup by sending his employees to hold up signs outside MTV’s TRL studios.

To jog your memory, J.Lo and Diddy started seeing each other around 1999 — when both were 30 — after meeting on the set of the music video for her song, “If You Had My Love.” In December 1999, they were arrested together on weapons and bribery charges after fleeing a nightclub shooting involving an artist signed to Diddy’s label. (Her charges were dropped and he was acquitted two years later.) He was also her date to the 2000 Grammy Awards, where she first wore the green Versace dress that birthed Google Images. The couple broke up in February 2001 amid rumors of infidelity, which J.Lo later told Vibe she suspected were true.

Speaking of infidelity, most outlets (Rolling Stone included) have referred to Diddy and J.Lo’s relationship as an affair — when they started seeing each other, he was living with Porter, his on-again, off-again-partner with whom he’d just welcomed a son. Porter, who died of lobar pneumonia in 2018, told Essence that throughout her ex’s relationship with J.Lo — and after she’d kicked him out of their shared house — Combs was “very, very intrusive,” calling her “50, 60 times a day” and making her feel “like my life was not my own.” Cassie (whose legal name is Casandra Ventura) also detailed in her lawsuit how, when she tried to leave Diddy, he frequently sent employees begging her — and sometimes threatening her — to come back to him. Per Rolling Stone, there was an unspoken “deal” of dating Diddy: that “the women who signed up for it were not allowed to walk away.”

This puts that 2021 “#tbt” post of Diddy and J.Lo under a much uglier light.

Diddy Allegedly Sent His Staffers to Win Back J.Lo