Rosie O’Donnell gave fans a glimpse into her reconnection with her daughter Chelsea, who is currently in prison.
The comedian took to InstagramThursday to share a text exchange between her and Chelsea, in which the two caught up and talked about her imminent release.
“Thank you mom I got my music back today,” Chelsea’s message began. “How are you? I’m trying to get ahold of the social worker to let her know the plans for when I get out, Hannah texted her for me.”
“Ok great,” O’Donnell responded. “Got my nails done — no more gel for me my nails are ruined. Are [you] reading a good book?”
Chelsea replied, telling her mom she was reading “The Legacy” book series and that she’s really enjoying it.
“And yeah, I havnt [sic] painted my nails in years but I remember that stuff breaking my nails,” she added.
In her post, the actress also included a touching throwback photo of her and her daughter smiling and hugging.
Back in June, the mother-daughter duo reunited when O’Donnel visited the 28-year-old in jail. At the time, the former “View” host shared an emotional poem about the experience.
After the visit, O’Donnell exclusively told Page Six that their reunion “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,” she added, noting that Chelsea cried when the visit was cut short due to a tornado warning.
“And that’s the first time I’ve seen, kind of, an empathetic emotion from her,” O’Donnell explained. “So, you know, she’s growing up and I hope that her future is brighter than this past decade has been.”
In February 2025, Chelsea appeared in court over felony bail jumping, resisting or obstructing an officer, and possession of methamphetamine and child neglect.
She was subsequently sentenced to six years of probation and warned of prison time in the event that she violated probation requirements — which included possession of a controlled substance.
Her probation was revoked and she was sentenced to jail last October.
In February, TMZ reported that a State of Wisconsin Department of Corrections report revealed that Chelsea had been accused of alleged assault after touching a man’s genitals without permission — a claim she denied to authorities, per the outlet.
Chelsea has had an estranged relationship with O’Donell, who adopted her as a baby in 1997, for most of her adult years.
The former “Rosie O’Donnell Show” host has previously shared that Chelsea was “born addicted” to drugs as her birth mother had been using while pregnant.
“I thought, ‘Well, love can cure everything,’ but I don’t know that that’s true,” O’Donnell later admitted.
O’Donnell has four other adopted children: son Parker, 31; son Blake, 26; daughter Vivi, 23; and her youngest, Clay, 13.
If you or someone you care about is affected by any of the issues raised in this story, call SAMHSA’s National Helpline at 1-800-662-HELP (4357).
The post Inside Rosie O’Donnell’s reconnection with jailed daughter Chelsea appeared first on Page Six.
