Sean “Diddy” Combs’ twin daughters, Jessie and D’Lila Combs, just hit a huge milestone, their high school graduation, and they did it while their dad remains in the middle of a criminal trial that’s making national headlines.
The Diddy twins’ graduation moment was bittersweet, with their father facing charges that could land him behind bars for life.
Jessie and D’Lila, both 18, took to Instagram to share a bunch of snaps from their graduation ceremony in Los Angeles on May 23. The sisters rocked matching white asymmetrical cocktail dresses underneath classic dark blue caps and gowns, striking poses with classmates, family, and friends. With big smiles, flowers, and diplomas in hand, the two looked proud and totally unbothered by the chaos surrounding their father.
The Diddy twins‘ graduation comes not long after they stunned in red dresses at their high school prom on May 17. The event, held at Harbor House in Los Angeles, saw Jessie and D’Lila making a grand entrance, late, of course, with the iconic line: “The party doesn’t start until we walk in. Saved the best for last.”
Diddy welcomed Jessie and D’Lila with the late Kim Porter in 2006. The girls are part of a big blended family, which includes their brother Christian, their half-brothers Justin Combs and Quincy Brown, their half-sister Chance Combs, and Diddy’s youngest daughter Love, whom he shares with Dana Tran. Despite the whirlwind of public scrutiny and legal drama surrounding the Bad Boy mogul, the twins have managed to stay focused and keep it classy during their personal milestone moments.
Meanwhile, things aren’t looking so picture-perfect for their dad. Diddy’s criminal trial officially began on May 12 after his September 2024 arrest. The music mogul, who is being held without bail at the Metropolitan Detention Center in Brooklyn, has pleaded not guilty to serious charges, including sex trafficking, racketeering, and transporting people to engage in prostitution. If convicted, Diddy could be looking at life behind bars.
Courtroom drama is unfolding fast, with key witnesses already testifying. Diddy’s former assistant, ex-girlfriend Casandra “Cassie” Ventura, her mom, makeup artists, and even rapper Kid Cudi have all taken the stand. The judge expects the trial to wrap up before July 4, but the case has already dragged the whole Combs family into the spotlight in ways they probably never imagined.
Jessie and D’Lila were spotted at the Manhattan federal courthouse on May 13, the same day Cassie began her testimony. The twins, along with their siblings and grandmother Janice Combs, have been attending court hearings, standing by their father even as the disturbing details keep surfacing.
Through it all, the Diddy twins’ graduation stands out as a rare bright spot in the Combs family’s timeline right now. While their dad battles for his freedom, Jessie and D’Lila are out here achieving big things, handling the pressure with style and grace. With diplomas in hand and their futures wide open, the twins are stepping into a new chapter, one that, hopefully, comes with more joy than courtroom headlines
Jamie Wells has a knack for getting the inside scoop on Hollywood’s biggest stars and up-and-coming talent. With a sharp eye for industry trends and an ear for viral moments, Jamie covers everything from red-carpet events to behind-the-scenes drama in movies, TV, and celebrity culture.
