Rosie O'Donnell's Prison Visit Was 1st Time She Spoke to Daughter in 10 Years
Rosie O'Donnell is opening up about her recent visit to a federal prison to spend time with her daughter, Chelsea O'Donnell, following her latest drug-related arrest.
"[The visit] was the first conversation I've had with her in 10 years that lasted more than 15 minutes," the comedian, 64, told Page Six in an interview published on Sunday, July 12. "The first time that I saw her in a consistent way was the four hours in the prison.
In October 2025, Chelsea was ordered to serve prison time after allegedly violating the terms of her six-year probation stemming from three back-to-back drug-related arrests. She was first arrested in September 025, on charges of drug possession and child neglect. She was arrested again on October 11, for drugs, and a third time on November 18, also for drugs.
"I have compassion for those struggling with addiction," Rosie exclusively told Us Weekly at the time, reacting to her daughter's incarceration. "Chelsea was born into addiction and it has been a painful journey for her and her children. We continue to love and support her through these horrible times. Prayers welcomed."
As part of her plea deal, Chelsea pleaded guilty to some charges while others were dropped. She was sentenced to 18 months in prison but the sentence was "stayed," meaning she would only have to serve probation as long as she did not get into any legal trouble for six years. Her probation was revoked after she allegedly failed to adequately attend and complete a drug rehab program and was accused of sexual assault.
She is currently serving her time at the Taycheedah Correctional Institution, a women's maximum-security prison located in Fond du Lac, Wisconsin.
Rosie told Page Six that her daughter cried during their visit, when the inmates and their visiting family members were informed visitation hours would be cut short due to weather.
"That's the first time I've seen, kind of, an empathetic emotion from her," the comedian told the outlet. "So, you know, she's growing up. And I hope that her future is brighter than this past decade has been."
The former The View co-host previously opened up about her visit to see Chelsea by turning to the written word, sharing a lengthy poem via social media in which she detailed her experience seeing her daughter behind bars.
"I arrive early. It's very hot. I'm wearing shorts. Waiting for her," Rosie wrote via Instagram on June 13, sharing what appeared to be a recent photo of the former TV host visiting her daughter in jail.
"In what looks like a children's nursery room, Disney murals on cement walls. Vending machines. Table 8 - I'm told to sit," she continued in the caption. "In one of the red chairs. Beige is for the inmate. The guard explained the rules."
Rosie added at the time, "A hug hello and goodbye only. No money exchanged. Hands above the table. No loud voices. The visit is 4 hours long There r worn out games to play. Scrabble - cards - chutes & ladders. Other families walk in."
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This story was originally published July 12, 2026 at 1:38 PM.