Jack Osbourne shares two cents on his sister Kelly's encounter with Diddy

Jack Osbourne thinks his sister Kelly Osbourne “ended up winning” after a run-in with music mogul Sean “Diddy” Combs.

During a recent appearance on the Inside of You podcast with Michael Rosenbaum, the 39-year-old reality star opened up about an unusual moment involving his sister and the disgraced rapper.

“Kelly got invited to a Diddy party when she was like 18,” Jack said. “He ran into Kelly, and some weird thing happened where his bouncer knocked her over, and he invited her to one of his parties.”

Jack noted there was plenty of speculation at the time about what really happened between the two. “I think she ended up winning that,” he added. “He gave her some diamonds and brought her to a party, and she went, ‘Later.’”

The encounter between Kelly and Diddy was previously detailed in season 2, episode 7 of The Osbournes, where her mother, Sharon Osbourne, had encouraged Kelly to pursue something more with Diddy.

“Wouldn’t it be cool if Kelly went out with Puff Daddy?” Sharon mused. “And I was Puff Daddy’s mother-in-law? Puff Mummy. I think they would be so cute together."

In the same episode, Kelly described Combs as “so manicured,” “such a gentleman,” and “so well put together” after attending one of his parties and showing off a watch he had gifted her.

However, Sharon responded with an awkward remark at the time, telling her then-single daughter, “I bet he’s got a nice old willy and all! I bet it’s smooth. I bet it’s oiled. I bet it’s just perfect.”

Kelly is now engaged to her longstanding boyfriend Sid Wilson, the DJ/turntablist from Slipknot. The proposal took place backstage during her father Ozzy Osbourne’s final Black Sabbath concert at Villa Park, Birmingham, on July 5, 2025, in front of family and friends.

Meanwhile, Combs is awaiting sentencing after he was convicted of two counts of transportation for prostitution of his ex-girlfriend, singer Cassie Ventura, and another woman known as "Jane" earlier this year. 

He was however found not guilty of the more serious charge of racketeering conspiracy as well as two charges of sex trafficking.