Speaking exclusively to Page Six in an article shared on Sunday, July 12, the comedian revealed that spending four hours with Chelsea while she was in prison led to what she described as "the first conversation I've had with her in 10 years that lasted more than 25 minutes." The pair’s relationship has faced public ups and downs over the past decade.
"And that's the first time I've seen, kind of, an empathetic emotion from her," she continued. "So, you know, she's growing up, and I hope that her future is brighter than this past decade has been."
She also recalled the moment Chelsea entered the visitation room, writing that her heart "skip[ped] a beat." O'Donnell described her daughter as looking healthy, calm and well-rested, and said they shared a long embrace before spending four hours talking.
View this post on Instagram“It’s heartbreaking to see someone you love so much in prison , as you know ? Prayers for your girl,” one wrote.
“This so vulnerable & beautiful @rosie. As a mother I can’t imagine how difficult this has been,” a third said.
Chelsea, who is the eldest of O'Donnell's five children, has faced ongoing legal troubles in recent years. In February 2025, she appeared in court on charges including felony bail jumping, resisting or obstructing an officer, possession of methamphetamine and child neglect. She was sentenced to six years of probation but was warned that jail time was possible if she violated the terms. After her probation was revoked in October 2025, she was sentenced to jail.
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