Rosie O’Donnell Posts Photo of Daughter Chelsea While She’s in Prison
Rosie O’Donnell is providing insight into her recent reunion with her daughter Chelsea O’Donnell, following a prolonged period of estrangement.
On Thursday, August 27, Rosie, 64, shared a heartfelt photo on Instagram from her visit to see Chelsea, 28, at Taycheedah Correctional Institution in Fond du Lac, Wisconsin. Chelsea is currently serving an 18-month sentence after breaching her probation linked to several arrests in 2024. The image captured Rosie embracing her daughter, who was dressed in a green button-down prison uniform, while Rosie wore a simple black T-shirt.
In addition, Rosie shared a screenshot of a text conversation with Chelsea.
“Thank you, mom, I got my music back today,” Chelsea texted her mother. “How are you? I’m trying to reach the social worker to discuss my plans for when I get out; Hannah texted her on my behalf.”
Rosie replied, “OK great – I got my nails done – no more gel for me, my nails are ruined. Are you reading a good book?”
Chelsea responded, “I am reading the Legacy series; it’s really good. She has a whole bunch of other books too. And yeah, I haven’t painted my nails in years, but I remember that stuff breaking my nails.”
Chelsea’s probation was revoked, and she was sentenced to jail in October 2025 after being arrested three times on drug-related charges in 2024, starting with an arrest that September for felony charges including neglecting a child and possession of methamphetamine.
In February 2025, Chelsea — a mother of four — pleaded guilty to resisting or obstructing an officer, felony bail jumping, and possession of methamphetamine. The following month, she received a sentence of six years of probation but faced incarceration if she violated several probation terms, including maintaining absolute sobriety and avoiding contact with known drug users or sellers.
In June, Rosie shared a poignant poem reflecting her visit to her daughter while incarcerated.
“I arrive early. It’s very hot. I’m wearing shorts. Waiting for her,” she wrote. “In what appears to be a children’s nursery room, Disney murals adorn cement walls. Vending machines. Table 8 — I’m instructed to sit. In one of the red chairs. Beige is for the inmate. The guard outlined the rules.”
In July, Rosie informed Page Six that her visit with Chelsea marked “the first conversation I’ve had with her in 10 years that lasted more than 15 minutes.”
“The first time I consistently saw her was over the four hours in the prison,” she noted.
Later that month, Rosie shared with People that Chelsea is now sober, which has “changed everything.”
“She ran away at 17 to her birth mother and to a community in Wisconsin heavily influenced by drugs. I recently visited her in prison, which was emotionally overwhelming,” she elaborated.
“I saw the child I once knew,” Rosie — who adopted Chelsea as a baby with her ex-wife Kelli Carpenter — continued. “She calls every day, and we have conversations.”
