Rosie O’Donnell is breaking her silence after her daughter Chelsea was sentenced to state prison for violating probation, sharing a raw and emotional message as the 28-year-old faces a troubling future behind bars.
Rosie O’Donnell, 63, is no stranger to public scrutiny, but this time, it’s personal.
The former talk show host and President Donald Trump-hating comedian took to Instagram to share a heartbreaking message following her 28-year-old daughter Chelsea’s sentencing to state prison after multiple felony arrests and a probation violation. The emotional plea has sparked waves of support – and left many wondering how the once-private family struggle spiraled into a very public crisis.
Daughter Chelsea
Chelsea is one of five children Rosie O’Donnell shares with her former partners. She and ex-wife Kelli Carpenter welcomed Chelsea, as a baby, through adoption, along with sons Parker (30) and Blake (25), and daughter Vivienne (22). O’Donnell later adopted a fifth child, Clay, now 12, with her late ex-wife Michelle Rounds.
Chelsea, 28, has four children of her own: Skylar Rose (born December 2018), Riley (January 2021), Avery Lynn (February 2022), and Atlas (October 2023).
Multiple felonies
Chelsea’s mounting legal troubles began in Wisconsin, where she was arrested three times between September and December of 2024. Her first arrest came on Sept. 10, when she was charged with multiple felonies, including neglecting a child and possession of methamphetamine, according to Us Weekly.
After posting bail, Chelsea was released – only to be arrested again a month later for additional felonies: jumping bail, resisting or obstructing an officer, and once again possession of meth.
A third arrest followed in November 2024 on similar felony charges, including possession of narcotic drugs. Chelsea appeared in court on March 31, 2025, and pled guilty to three charges: resisting or obstructing an officer, felony bail jumping, and possession of methamphetamine. She was sentenced to six years of probation – two years for each count – with strict conditions: total sobriety, no firearms, and zero contact with known drug users or dealers.
At the time of her sentencing, Chelsea was warned that any violation of her probation terms could result in prison time.
And by Oct. 22, 2025, court records confirmed Chelsea had violated those conditions. As a result, her probation was revoked, and she was sentenced to state prison, as reported by People.
Awaiting transfer
While full details of Chelsea’s revocation are unknown at this time, Us Weekly reports that an official from the Marinette County Treatment Drug Court Team said she was in violation due to sexual assault allegations. The woman has been booked into Wisconsin’s Marinette County Jail, where she awaits transfer to a state prison facility.
At Marinette County, she remains in general population. According to jail administrator Jake Roberts, Chelsea and other inmates have access to a dayroom, television, board games like Uno and chess, and can communicate with loved ones through a message kiosk and video calls, TMZ reports.
The conditions may offer a hint of normalcy, but the reality remains grim: Chelsea is facing a future behind bars – and her famous mother is publicly asking for strength.
‘Loved her then, I love her now’
O’Donnell, breaking her silence on the situation, shared an emotional Instagram post featuring a photo of Chelsea as a child.
“My child chelsea belle – before addiction took over her life – i loved her then i love her now as she faces a scary future – prayers welcomed – #addiction awareness #love #family,” Rosie O’Donnell wrote in an Instagram caption alongside the image of a young Chelsea, smiling awkwardly in a pink sweater with striped turtleneck.
In a separate statement shared with People, the comedian added, “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.”
Though she’s known for speaking her mind – whether battling politics or making audiences laugh – O’Donnell’s message this time is one of quiet vulnerability.
Please let us know what you think of O’Donnell’s message for prayers, and then share this story so we can hear from others!
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