“The first time that I saw her in a consistent way was the four hours in the prison,” the comedian said of her 28-year-old child

NEED TO KNOW

• Rosie O’Donnell said in a new interview that her June prison visit with her daughter, Chelsea O’Donnell, marked their first conversation in 10 years that lasted longer “than 25 minutes”
• The comedian added that it was the first time she’s seen “empathetic emotion” in 28-year-old Chelsea, who was sentenced to prison in October 2025
• Chelsea and Rosie’s relationship will be the subject of the comedian’s next one-woman show

Rosie O’Donnell has shared more insight into her emotional visit to see daughter Chelsea O’Donnell in prison last month.

In an interview with Page Six published on Sunday, July 12, the comedian and actress, 64, said the pair’s chat behind bars in Wisconsin, which Rosie previously documented with a poem shared on Instagram in June, “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,” Rosie added to the outlet.

“And that’s the first time I’ve seen, kind of, an empathetic emotion from her,” she continued. The comedian also said that Chelsea, 28, cried when the pair’s visit ended early due to a tornado warning in the area.

The A League of Their Own actress — who is a mom to five children total, four with her ex-wife, Kelli Carpenter, and her fifth with late ex-wife Michelle Rounds — also spoke with Page Six about some of her hopes for Chelsea’s future.

The 28-year-old has been sober for “almost two years now,” Rosie said, “and that’s a very big part, you know.”

“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,” the mother added.

“So, you know, she’s growing up,” Rosie then said of her daughter. “I hope that her future is brighter than this past decade has been.”

Chelsea’s relationship with her comedian mom will be explored in Rosie’s next one-woman show, she also revealed to Page Six. Her daughter has even seen some of the material.

“I’ve asked for Chelsea’s input,” the actress told the outlet. “I sent it to her and said, ‘I’d really love to get you — your voice heard and just now what I perceive to be your voice … and I think she’s ready to do that now.”

Chelsea had her probation revoked and was sentenced to jail in October after she was arrested three times in 2024, starting with a September arrest on multiple felony charges, including neglecting a child and possession of methamphetamine.

She appeared in court for sentencing on the three felony counts she pleaded guilty to in February 2025: resisting or obstructing an officer, felony bail jumping and possession of methamphetamine.

In March 2025, she was sentenced to six years probation — a two-year sentence for each of the three guilty counts. Chelsea was told she could face prison time should she violate any of the probation requirements, which included absolute sobriety, no possession of alcohol or another controlled substance without a valid prescription, no contact with any known drug users or sellers and no possession or ownership of any firearm. 

Her probation was revoked, and she was sentenced to prison time on Oct. 22, per court documents previously obtained by PEOPLE.

Rosie previously reflected on the experience of visiting Chelsea in prison through poetry she shared alongside a mother-daughter selfie on Instagram on June 12. The photo, seemingly taken during the visit, showed Chelsea smiling as she wrapped her arms around the star.

In her poem, Rosie wrote that she and Chelsea “have been thru so much,” adding of her child: “It’s hard enough for her / She turns 29 this summer / And all I see when I look at her / Is a blonde baby in diapers.”

“It was a big day for both of us,” the mom of five penned elsewhere of the emotional visit, for which she said she was “proud of us both.”

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Rosie also shared some of her thoughts from “before” the visit on Substack. “She’s not fighting it anymore / This relationship we have / Her sobriety helps so much / Gives me hope,” she wrote of Chelsea. The 28-year-old now calls Rosie from prison “daily,” she said.

Rosie added in the poem that the mother-daughter pair have “gotten closer / Thru these tense times / And I’m grateful for that. That she’s alive.”

“Looking forward to her release / Planning her post-prison / journey / Drug free / Getting back with her children / Making amends / Dreaming of peace / For the first time / As am I,” she then wrote.

If you or someone you know is struggling with substance abuse, please contact the SAMHSA helpline at 1-800-662-HELP.

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