Daughter of Trump-hating comedian given 'scary' prison sentence

Rosie O’Donnell is reaching out for empathy and assistance as her daughter, Chelsea, grapples with addiction and encounters fresh legal troubles.

On Wednesday, the 62-year-old star of A League of Their Own posted a poignant message on Instagram. The post included a childhood photo of Chelsea, now 28, whom Rosie adopted when she was an infant.

“This is my child, Chelsea Belle, before addiction took over her life. I loved her then, and I love her now as she faces an uncertain future,” O’Donnell shared. “Prayers welcomed. #addictionawareness #love #family.”

This heartfelt message follows the revocation of Chelsea’s probation earlier this month, leading to a prison sentence imposed on October 22, as detailed in court documents reviewed by Us Weekly.

The publication noted that a representative from the treatment drug court cited Chelsea’s custody since September 9, mentioning that “she was in violation due to allegations of sexual assault.”

The representative also remarked that “Chelsea had not demonstrated significant progress in the treatment drug program.”

Rosie O'Donnell is asking for compassion and support as her estranged daughter, Chelsea, continues to struggle with addiction and faces new legal consequences; seen in 2016

Rosie O’Donnell is asking for compassion and support as her estranged daughter, Chelsea, continues to struggle with addiction and faces new legal consequences; seen in 2016 

‘The facts surrounding this request have been staffed with the Marinette County Treatment Drug Court Team and have been deemed sufficient grounds to warrant termination from the Marinette County Treatment Drug Court Program,’ the filing read. 

An officer told Us Weekly that Chelsea will be transferred to the a medium-security prison, Taycheedah Correctional Institution, in Wisconsin. 

In a statement to People, O’Donnell shared her continued empathy and sorrow: ‘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’s struggles have been ongoing. 

She was first arrested in Wisconsin in September 2024 on multiple felony charges, including child neglect and possession of methamphetamine.

After posting bail, she was arrested again a month later on additional felony counts, including bail jumping and resisting or obstructing an officer. 

A third arrest followed that November for possession of methamphetamine, bail jumping, and possession of narcotic drugs.

In March 2025, Chelsea pled guilty to three felony counts, resisting or obstructing an officer, felony bail jumping, and possession of methamphetamine, and was sentenced to six years of probation, two years for each count. 

Her misdemeanor charges for drug paraphernalia and narcotic possession were dismissed at the time.

Under the conditions of her probation, Chelsea was required to maintain absolute sobriety, avoid known drug users or sellers and refrain from possessing alcohol, firearms, or any controlled substances without a prescription.

On Wednesday, the A League of Their Own star, 62, shared a heartbreaking Instagram post featuring a much younger photo of her daughter, Chelsea, now 28 (pictured in 2006)

On Wednesday, the A League of Their Own star, 62, shared a heartbreaking Instagram post featuring a much younger photo of her daughter, Chelsea, now 28 (pictured in 2006)

Her post comes after Chelsea's probation was revoked earlier this month, resulting in a prison sentence handed down on October 22

Her post comes after Chelsea’s probation was revoked earlier this month, resulting in a prison sentence handed down on October 22 

Despite those terms, court documents confirm her probation has since been revoked. 

Chelsea is a mother of four young children: daughters Skylar Rose, 6, Riley, 4, and Avery Lynn, 3, and son Atlas, who turned one this month.

O’Donnell previously confirmed Chelsea’s legal troubles in a 2024 Instagram post, writing: ‘So yes, this is true — after being bailed out by her birth mother — Chelsea was arrested again. She is facing many charges related to her drug addiction. We all hope she is able to get the help she needs to turn her life around.’

Last year, Chelsea spoke to DailyMail.com from jail, saying her mother had taken a tough love approach and refused to bail her out.

‘When I called Rosie to ask her to bail me out, she told me flat out, ‘You belong in there,’ Chelsea said. ‘I really can’t help you get out of there; I don’t want you to kill yourself. I don’t want to be responsible for you killing yourself.’

At the time, Chelsea also expressed frustration that her mother appeared more focused on supporting the Menendez brothers’ bid for freedom than helping her own daughter. ‘My mother is more interested in getting the Menendez brothers released from prison than getting me out,’ she said. ‘I have a drug problem. I need to go to rehab, but I never killed anyone like the Menendez brothers.’

A representative for O’Donnell told Us Weekly in 2024, ‘The family hopes that she gets the help she needs.’

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