Cassie once said she felt like Jennifer Lopez while dating Diddy, says rapper's former bodyguard Roger Bonds

Roger Bonds, Sean "Diddy" Combs' former bodyguard, claimed that Cassie Ventura once told him she felt like Jennifer Lopez during the early days of her relationship with the rapper. Both women previously dated the rapper at different times. While Lopez and Diddy dated between 1999 and 2001, Ventura and Diddy dated on and off between 2007 and 2018.

Roger Bonds appeared for an interview on VladTV on June 15, 2025, where he alluded to Cassie Ventura's amazement with life after she began dating Diddy. The former bodyguard recounted an alleged incident of Cassie's disbelief that she was smoking weed with Bonds back when she first started dating Diddy in 2008, saying:

"The first time me and Cassie smoked some weed together in Miami in like 2008, I think it was when she first started coming around, and I think she said, 'Oh my God, I can't believe I'm smoking some weed with Puff's security.' And I looked at her like, 'Huh?' "

He continued that the R&B singer once allegedly told him she felt like Jennifer Lopez while going to a club. Bonds also accused Diddy of taking advantage of Ventura, who met the music mogul when she was 19 years old. Diddy had been 17 years her senior when she first met him.

"And one time I had to get in a club and she said, 'I feel like Jennifer Lopez.' I'm saying to myself like, 'What are you talking about?' So, I can see that. He found a kid, yo, he found a kid, and he took advantage of a kid that he knew wanted to be a star," Bonds said.

Cassie Ventura was the star witness in the government's federal case against Diddy. The rapper is currently on trial for five charges, including "s*x trafficking, racketeering conspiracy, and transportation to engage in prostitution." During her four-day testimony between May 13 and 16, Ventura recounted the alleged abuse and sexual assault she faced during her relationship with Diddy.

She also accused him of wielding his power over her to coerce her to participate in "freak-offs" with several male escorts, which he allegedly filmed and used as material to blackmail her.

Exploring Diddy's relationship with Jennifer Lopez

Diddy and Jennifer Lopez were reportedly in a relationship from 1999 to 2001. According to The Root, the pair met on the set of Lopez's If You Had My Love music video in 1999. Their relationship was in the limelight after the couple was allegedly involved in a shooting at a New York club in December 1999, leading to their arrest.

Jennifer Lopez, Diddy, and fellow rapper Shyne were arrested after the police found a stolen gun in their car. According to The Guardian, the couple was charged with "criminal possession of stolen property" following the shootout, which left three people injured. While Lopez's charges were dropped, both Diddy and Shyne were tried for their involvement in the shooting.

While Diddy was acquitted, Shyne was found guilty on five different charges, including "first-degree assault, reckless endangerment and criminal possession of a weapon." No one was charged or convicted for the shooting.

Lopez and Combs continued their relationship till 2001. According to The Root, they called it quits around Valentine's Day in 2001, with Diddy's publicist releasing a statement at the time that read:

“Mr. Combs confirmed that he and his love, Jennifer Lopez, have, in fact, broken up. He wanted to put all the rumors surrounding their relationship to rest. At this difficult time, we ask that you respect his privacy.”

During a 2003 interview with Vibe Magazine, Jennifer Lopez claimed their relationship ended because the rapper was unfaithful to her. She added that the relationship had her "crying, crazy and going nuts, it really took my whole life in a tailspin."

“I never caught him [cheating] but I just knew. He’d say he was going to a club for a couple of hours and then never came back that night. I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?” Lopez said.

Jennifer Lopez has not publicly commented on Diddy's arrest and his ongoing s*x trafficking trial. Speculations of Lopez testifying at the trial have circulated on social media due to her involvement with the rapper. However, this was not confirmed by official sources at the time of writing this article.

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