Rosie O’Donnell is opening up about a deeply emotional reunion with her daughter Chelsea, revealing that their recent prison visit marked the longest conversation they’ve had in more than ten years. The 64-year-old comedian visited her 28-year-old daughter at Taycheedah Correctional Institution in Wisconsin last month and told Page Six that the visit “was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes”. “The first time that I saw her in a consistent way was the four hours in the prison”.
Chelsea, whom Rosie adopted as a baby in 1997 with ex-wife Kelli Carpenter, is currently serving an 18-month sentence at the women’s maximum-security prison after her probation was revoked in October 2025. She had been arrested three times between September and November 2024 on multiple felony charges, including child neglect and possession of methamphetamine. In February 2025, she pleaded guilty to felony bail jumping, resisting an officer, and drug possession before her probation violation led to incarceration.
The visit, which was cut short due to a tornado warning, brought Chelsea to tears, a moment Rosie described as significant. “That’s the first time I’ve seen, kind of, an empathetic emotion from her,” she told Page Six. Rosie also shared that Chelsea has been sober for nearly two years, something she calls “a very big part” of their healing. “She was born addicted, and when I was adopting, I thought, ‘Well, love can cure everything,’ but I don’t know that that’s true,” she reflected.
The mother-daughter relationship will be the focus of Rosie’s next one-woman show, and she has been including Chelsea in the creative process. “I’ve asked for Chelsea’s input. I sent it to her and said, ‘I’d really love to get you, your voice heard,'” Rosie explained. After years of estrangement that began when Chelsea ran away from home at 17 in 2015, the pair are now speaking daily. Rosie ended with a note of hope: “She’s growing up, and I hope that her future is brighter than this past decade has been”.
