Rosie O’Donnell Speaks Out About Daughter Chelsea’s ‘Scary Future’ as She’s Given Prison Time

The former talk show host took to her Instagram page on Wednesday to share a message to her troubled daughter, who has a history of run-ins with the law.

Sharing a photo of Chelsea — who O’Donnell adopted as a baby with then-partner Kelli Carpenter — Rosie 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.”

She added, “prayers welcomed,” with the hashtags #addiction awareness #love and #family.

In a statement to Us Magazine, which broke the news of Chelsea’s prison sentence for allegedly violating the terms of her probation, O’Donnell also said, “I have compassion for those struggling with addiction — chelsea was born into addiction and it has been a painful journey for her and her children.”

She added, “we continue to love and support her through these horrible times. prayers welcomed.”

Chelsea is mother to four children: daughters Skylar Rose (born December 2018), Riley (born January 2021) and Avery Lynn (born February 2022), and son Atlas (born October 2023).

Per Us Magazine, Chelsea was given prison time after she was accused of violating probation earlier this month, with an official from drug treatment court reportedly citing sexual assault allegations.

The Marinette County Sheriff’s Office confirmed to the outlet that she’s been in custody since September 9 and will be transferred to Taycheedah Correctional Institution soon; she’ll either serve her sentence there or another prison. No additional details on the sentence, including its length, have been revealed.

In September 2024, Chelsea was arrested on felony child neglect and drug possession charges. A month later, she found herself behind bars again for similar offenses. And in November 2024, she was arrested a third time on multiple felony charges related to methamphetamine and narcotic possession.

In March 2025, Chelsea was sentenced to six years of probation, with strict conditions including sobriety and no contact with known drug users. She was also reportedly required to obtain a high school diploma or GED and undergo a mental health evaluation.

A month later, in April, O’Donnell took to her Substack and claimed her daughter was doing well.

“a few months ago a judge in Wisconsin told her he was proud of her she had completed treatment,” she wrote at the time, adding that she then got a phone call from her daughter.

“the phone rang with her number and she said hello with so much energy so much joy – self confidence,” she continued, saying Chelsea told her, “‘Mom – I got my high school diploma ten years too late … but I got it – today im holding it in my hands.'”

“she is doing so well now in spite of the tabloid fodder, she’s working on herself, aren’t we all,” O’Donnell wrote, concluding that she was “proud of her” and clarifying the post was shared with Chelsea’s permission.