It has been a tumultuous summer for Sean "Diddy" Combs, the music mogul whose life has played out as much in courtrooms as on the charts. Just days after a judge threw out the majority of a high-profile sexual assault lawsuit against him, Combs’ family found itself in the headlines for a very different reason—this time, at a California amusement park.
On Saturday night, August 16, 2025, Jessie and D’Lila Combs—Diddy’s 18-year-old twin daughters—were removed from a rollercoaster at the Orange County Fair in Southern California. The reason? According to TMZ and other outlets, the sisters allegedly ignored three separate warnings from ride staff to put away their phones before the ride began. Dressed in matching pink sweatsuits, the twins were seen in a video sitting with friends as a ride operator approached, delivering a final warning. The footage, which quickly made the rounds online, shows the group leaving the ride without further incident.
Insiders told TMZ that the situation escalated because the conductor was being "rude" in his requests, but sources with direct knowledge clarified that Jessie and D’Lila were not ejected from the fair itself. Instead, they were offered tickets to return to the attraction at a later time—a minor consolation after the public embarrassment.
While this incident might have been the biggest story for most families, it was only a footnote in the ongoing legal drama surrounding their father. Sean Combs, known to the world as Diddy, remains incarcerated at the Brooklyn Metropolitan Detention Center, awaiting sentencing after being found guilty on two counts of violating the Mann Act. The verdict, delivered in July 2025, acquitted him of more serious racketeering conspiracy and sex trafficking charges, but the Mann Act convictions carry a potential sentence of up to 10 years per count. Sentencing is scheduled for October 3, 2025.
According to The Blast and TMZ, Diddy’s family has rallied around him during this difficult period. Last week, a large group of relatives—including his mother, Janice Combs; his sons, Christian "King" Combs and Justin Combs; his youngest daughter, Love; and Dana Tran, Love’s mother—visited the rapper in jail. Notably absent from the visiting party were Jessie and D’Lila, though the twins had attended their father’s six-week-long trial. For Dana Tran and Love, the visit was their first time at the courthouse, highlighting the family's efforts to support Diddy despite the legal storm swirling around him.
Meanwhile, Diddy’s legal team has gone on the offensive, arguing that his so-called "swingers" lifestyle with ex-girlfriends should not be grounds for continued incarceration. In a petition for his release, his lawyers wrote, "This was a lifestyle, one that both Ms. Ventura and Jane chose. One, they all, as grown adults, had a right to choose." The defense continued, "Like many aspects of sex and intimacy, it was not without its complications, its bouts of jealousy, and, at times, its frustrations. But that is a hallmark of any serious romantic relationship, and that is what these were, serious, long-term romantic relationships." The letter went further, claiming, "There has literally never been a case like this one, where a person and his girlfriend arranged for adult men to have consensual sexual relations with the adult long-term girlfriend as part of a demonstrated 'swingers' lifestyle and has been prosecuted and incarcerated under the Mann Act."
Despite these arguments, Judge Arun Subramanian has denied Diddy bail several times, ruling that there were no "exceptional reasons" to justify his release before sentencing. Reports suggest that, although the maximum sentence is 10 years per count, it is unlikely Diddy will receive the harshest penalty. Still, the uncertainty looms large for the Combs family as October approaches.
Adding another layer to Diddy’s legal woes, a lawsuit filed by Sara Rivers—who appeared as a contestant on Making the Band 2 over 20 years ago—was largely dismissed last Thursday, August 14, 2025. Rivers had accused Combs of groping her at his New York recording studio and filed a complaint earlier this year at the height of the legal scrutiny surrounding the music mogul. The suit also named Universal Music Group, Bad Boy Records, and Paramount’s MTV, alleging assault and battery, sexual harassment, and hostile work environment. Rivers sought at least $60 million in damages.
However, as reported by The Blast and TMZ, U.S. District Judge permanently dismissed 21 of the 22 claims, most of which were related to workplace issues. The court found that the alleged misconduct occurred more than 20 years ago, far beyond the one-to-ten-year statute of limitations for such claims. Combs’ lawyer, Erica Wolff, stated, "From the outset, we have said these claims were meritless, time-barred, and legally deficient. The Court agreed, finding no legal basis to allow them to proceed."
Only one claim remains: an alleged violation of New York’s Gender-Motivated Violence Protection Act, which covers sex crimes. Whether this claim will proceed hinges on a federal appeals court’s decision regarding a recent amendment to the law, which allows lawsuits to be filed for two years even if the previous window for legal action has closed. The court’s final opinion on the dismissal is expected soon. Rivers’ attorney, Ariel Mitchell, did not immediately respond to requests for comment.
Complicating matters, Combs has also filed a $100 million defamation suit against Mitchell over comments she and her client, Courtney Burgess, made regarding his alleged involvement in sex parties with celebrities and minors. The legal battles, it seems, are far from over.
All of this comes as Diddy’s public image, once synonymous with success and swagger, faces perhaps its greatest test yet. The juxtaposition of his daughters’ amusement park mishap with his own ongoing court cases paints a picture of a family under extraordinary pressure—caught between the glare of celebrity and the grind of the legal system.
As October’s sentencing date draws near, the world watches to see what fate awaits Sean Combs and how his family, both in the spotlight and behind the scenes, will continue to navigate the fallout. For now, the Combs name remains as headline-grabbing as ever—just not always for the reasons they might have hoped.
