Chelsea O’Donnell, daughter of outspoken liberal activist and former talk show host Rosie O’Donnell, is heading to prison after a Wisconsin judge ruled that she violated the terms of her probation. The decision came down on October 22 following new allegations and setbacks in her ongoing legal struggles, according to court records reviewed by Us Weekly.
The 28-year-old had previously been placed on probation after a series of drug-related arrests and was participating in a court-mandated treatment program as part of her sentence. However, court officials said she failed to make meaningful progress in the program. The final decision to terminate her participation came after she was allegedly connected to a sexual assault-related probation violation, though specific details about the allegation have not been publicly released at this time.
“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,” a court filing stated.
Chelsea O’Donnell has reportedly been in custody since September 9, well before the court’s most recent decision. Officials from the Marinette County Sheriff’s Office confirmed that she will now be transferred to the Taycheedah Correctional Institution, a women’s prison in Wisconsin. She is expected to serve out her sentence there unless she is reassigned to another correctional facility.
Chelsea is the adopted daughter of Rosie O’Donnell, who has long been known for her vocal criticism of former President Donald Trump and her outspoken views on various political and social issues. In light of her daughter’s legal and personal troubles, Rosie O’Donnell has taken to social media to express concern and ask for public support.
“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,” Rosie wrote on Instagram shortly after the news broke.
As reported by Breitbart,
Chelsea O’Donnell, the adopted daughter of leftist entertainer Rosie O’Donnell, was sentenced to prison last week, after she violated her probation in a drug case. pic.twitter.com/KO5B0FpYtK
Should Chelsea O’Donnell receive support during her prison sentence?— Breitbart News (@BreitbartNews) October 30, 2025
In a separate statement to Us Weekly, Rosie 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 children. We continue to love and support her through these horrible times. Prayers welcomed.”
Chelsea’s legal troubles stretch back several years. Earlier in 2025, she was sentenced to six years of probation after multiple arrests related to drug charges. The terms of her probation included regular participation in a court-supervised treatment program, check-ins with officials, and staying free from any new legal trouble. The recent allegations and her failure to meet treatment expectations led the court to revoke her probation and order incarceration.
While Rosie O’Donnell is well known in the public eye, Chelsea has had a much more troubled path. Her struggles with addiction and brushes with the law have been largely kept private, but recent developments have pushed her story into the spotlight.
Officials have not released how long Chelsea is expected to remain in prison or whether additional charges might be filed in connection with the recent allegations. Her legal team has not made a public statement regarding the court’s decision or any plans for appeal.
As Chelsea begins her prison sentence, attention will likely remain on how the O’Donnell family handles the next steps. For now, Rosie’s message remains focused on support and prayer for her daughter and her grandchildren during what she described as a “scary future.”
