Rosie O’Donnell has revealed that she recently visited her daughter Chelsea in a Wisconsin prison.
Rosie Visits Daughter In Prison
Chelsea, 28, was sentenced to jail back in October of 2025 after having her probation revoked. This came after she was arrested three times in 2024.
Though Rosie and Chelsea have been estranged at times, she claimed that her daughter requested the visit. Rosie then took to Instagram to share a selfie of herself and Chelsea at the prison as she reflected on their visit in a poem.
“I arrive early, It’s very hot, I’m wearing shorts, Waiting for her,” wrote Rosie, 64.
“The guard explained the rules,” Rosie continued. These rules were ” hug hello and goodbye only, No money exchanged, Hands above the table, No loud voices.”
‘We Have Been Thru So Much…’
Rosie claimed that her heart skipped “a beat” when Chelsea walked in. She said that Chelsea “looks good, healthy calm, rested blue eyes, clear skin, in her green uniform.”
“We embrace,” Rosie recalled. “She smells familiar, holds on tight, I stare into her eyes. We have been thru so much.”
Chelsea’s own four young children have not visited her, something that Rosie acknowledged pains her daughter “very much.” Despite this, the comedian tried “to stay present” during the prison visit. “I try to shake the sadness,” she said.
Referring to Chelsea, Rosie wrote, “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.”
Unfortunately for them, their visit was “cut short” due to weather. She was only able to give Chelsea a ““quick hug” before returning to her car.
“It storms all the way to the hotel / As I try to process / All that’s happened,” Rosie wrote. “It was a big day for both of us.”
Rosie slept “for hours” after the visit. Despite how difficult it was, Rosie insisted that she was “proud of us both.”
“Unconditional love / Simply the only way / Thru motherhood,” Rosie concluded. “Love and forgiveness a must / Even when it seems impossible / Especially then / We live we learn we grow / Even at 64.”
Chelsea Is ‘Not Fighting It Anymore’
Rosie previously took to Substack to share her thoughts “before” the visit.
“She’s not fighting it anymore, This relationship we have,” Rosie wrote. “Her sobriety helps so much
Gives me hope.”
When Rosie told her daughter that she “may cry” when she sees her in prison clothes, Chelsea replied, “Why mom — it’s not bad in here — I have friends now.”
Though Rosie is now living abroad in Ireland after fleeing there over Donald Trump’s second presidential victory, she claims that she and Chelsea talk “daily.” According to Rosie, they have “gotten closer / Thru these tense times / And I’m grateful for that.”
“That she’s alive,” Rosie added. “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.”
Chelsea’s Probation Revoked
In February of 2025, Chelsea plead guilty to three charges: resisting or obstructing an officer, felony bail jumping and possession of methamphetamine. One month later, she was sentenced to six years of probation.
Chelsea was warned at the time that she could face prison time if she violated the terms of her probation. These terms included no alcohol possession or any other controlled substance, no contact with those who are known to use or sell drugs, and no possession of a firearm.
In October of 2025, Chelsea had her probation revoked and was sentenced to prison. Afterwards, Rosie told People Magazine, “I have compassion for those struggling with addiction – Chelsea was born into addiction and it has been a painful journey for her and her four young children. We continue to love and support her through these horrible times. Prayers welcomed.”
Whether you like Rosie or not, it’s clear that Chelsea has had some major struggles in life. Especially given that she’s a mother of four young children, we can only hope that she gets the help she needs to turn her life around.