Rosie O’Donnell Asks for ‘Prayers’ for Daughter Chelsea, 28, as She Faces ‘Scary Future’ amid New Prison Sentence

Rosie O’Donnell is reaching out for compassion and prayers as her daughter Chelsea faces new challenges.

On Wednesday, Oct. 29, the actress posted a throwback photo of Chelsea, now 28, on Instagram, showing her in a pink and red striped turtleneck layered under a pink sweater. Alongside the image, O’Donnell wrote:

“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. #addictionawareness #love #family”

Her plea came after Chelsea’s probation was revoked and she was sentenced to prison on Oct. 22, according to court documents. The Marinette County Treatment Drug Court Program has not commented on the case.

In a statement, O’Donnell expressed her empathy for those battling addiction:

“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.”

Chelsea, whom O’Donnell adopted as a baby, has faced a series of legal troubles. Between September and December 2024, she was arrested three times in Wisconsin. Her first arrest, on Sept. 10, involved multiple felony charges including child neglect and methamphetamine possession. After posting bail, she was arrested again a month later for bail jumping, resisting or obstructing an officer, and methamphetamine possession.

A third arrest followed in November on similar charges. In February, Chelsea pled guilty to three felony counts — resisting or obstructing an officer, felony bail jumping, and methamphetamine possession — and appeared in court for sentencing on March 31.

That day, her misdemeanor charges for possession of drug paraphernalia and narcotic drugs were dismissed. She received six years of probation — two years per count — and was warned that any violation could lead to prison time.

Her probation terms included maintaining absolute sobriety, avoiding controlled substances or alcohol without a prescription, refraining from contact with known drug users or sellers, and not possessing firearms.

Chelsea, a mother of four, welcomed daughter Skylar Rose in December 2018, daughter Riley in January 2021, daughter Avery Lynn in February 2022, and son Atlas in October 2023.