Diddy Made Bad Boy Staff Hold Signs Outside MTV's 'TRL' to Try and Win Back Jennifer Lopez, Ex-Intern Alleges

The disgraced mogul dated the multi-hyphenate from 1999 to 2001.

Sean Combs and Jennifer Lopez sit together at an event; Sean in a pinstripe suit, Jennifer in a low-cut, floral-patterned dress
Image via Getty / Steve Granitz Archive 1 / WireImage
Sean Combs and Jennifer Lopez sit together at an event; Sean in a pinstripe suit, Jennifer in a low-cut, floral-patterned dress

Sean "Diddy" Combs allegedly forced his Bad Boy employees to stand outside the Times Square studio of MTV's TRL and hold signs with the hopes of winning back Jennifer Lopez following their breakup in 2001.

Damien Vasquez, a former intern at Bad Boy, disclosed the unusual alleged assignment in the explosive Rolling Stone report from Cheyenne Roundtree and Nancy Dillon on Combs. The investigative piece uses the anecdote to emphasize a concerning trend involving the disgraced mogul and the women he has dated.

Diddy wielded his power to bend people to his will, sources claim, once sending his staffers to try and win back ex Jennifer Lopez by camping outside TRL studios with Spanish-language signs

We found some of those signs: https://t.co/vJ9ZyYFwRR

— Cheyenne Roundtree (@cheyenne_round) May 29, 2024
Twitter: @cheyenne_round

Combs allegedly used a "network of operatives" to find Cassie whenever she went into hiding and implored her to return. A Bad Boy executive allegedly gave her an ultimatum: return Diddy's calls or her music would not be released.

This alleged behavior dates back to the late Kim Porter, who once told Essence that Combs called her "50, 60 times a day" after they ended their relationship. The split occurred after a then-pregnant Porter found out Diddy had a child with another woman. She also dealt with several allegations of cheating on his part, which included Lopez.

Former Bad Boy president Kirk Burrowes believes Diddy's behavior can be linked to previous losses in his life, such as the fatal shooting of his father Melvin at a young age. "He is fortified now with the money and power," Burrowes said, adding that "abandonment and the act of leaving can bring about vicious results."

Burrowes added, "And the women catch it the worst."

Roundtree and Dillon interviewed more than 50 people over the past six months about their encounters with Combs for the Rolling Stone piece. Those who were willing to speak range from former friends to Bad Boy employees to artists once signed to the label.

Bad Boy for Life. A six-month investigation by Rolling Stone.

For decades, Sean “Diddy” Combs was hip-hop’s boisterous showman. Now, dozens of former friends, employees, and Bad Boy artists allege an abusive, violent figure behind the facade.

Read: https://t.co/fmuhyrXaNH pic.twitter.com/FvuXLB3KiH

— Rolling Stone (@RollingStone) May 29, 2024
Twitter: @RollingStone

Former students who attended Howard University at the same time as Combs allege they witnessed an incident in which he struck his girlfriend with a belt. A Howard alum was admittedly unsurprised to hear about abuse allegations against Diddy.

"You’re already an abuser [in college]," the alum said. "You were already feeling you had to have certain power over people."

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