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Rosie O’Donnell’s daughter, Chelsea, is staring down the grim reality of a prison sentence after a Wisconsin judge revoked her probation in October 2025. This decision marks a significant turn in the life of the 28-year-old mother of four, who was originally given a chance to avoid incarceration by participating in a drug court program designed to aid rehabilitation.
The revocation stems from serious violations of her probation terms, which included allegations of sexual assault. While officials have opted not to disclose intricate details of the incident, these accusations were deemed substantial enough to justify her removal from the program.
Reasons for Chelsea O’Donnell’s Probation Revocation: Assault Allegations
The Marinette County Treatment Drug Court Team evaluated Chelsea’s situation and concluded that both the allegations and her insufficient progress in the program warranted her termination. The severity of these new claims left the judge with no choice but to activate the prison sentence that had been previously suspended.
Chelsea’s legal troubles began in 2024 with a series of arrests on charges such as methamphetamine possession, child neglect, and bail jumping. In January 2025, she entered a guilty plea, which resulted in a six-year probation sentence under strict sobriety conditions. Despite the opportunity for rehabilitation, her repeated violations have now led to a daunting future behind bars.
Explanation of Chelsea O’Donnell’s Incarceration
Chelsea’s path to prison began with three arrests in 2024 for charges including methamphetamine possession, child neglect, and bail jumping. In January 2025, she pleaded guilty and was sentenced to six years of probation with stringent sobriety conditions.
However, she incurred multiple violations, such as issues with medication, missed appointments, dishonesty, and work suspensions, culminating in her September 2025 detention. The hearing on October 22 activated her previously stayed 18-month sentence.
Rosie O’Donnell’s daughter, Chelsea O’Donnell, is facing serious legal trouble again😳
New records detail allegations of sexual misconduct and probation violations that led to her jail sentence in Wisconsin.https://t.co/JVWgVqknBl
— The Blast (@TheBlastNews) February 25, 2026
Details on Chelsea O’Donnell’s Sexual Assault Allegation and Probation
The sexual assault claim was the tipping point in a long history of non-compliance. Chelsea’s probation mandated complete sobriety and active involvement in drug court programming, but officials reported that she did not make notable progress throughout 2025.
The treatment court team reviewed her situation and unanimously agreed on termination, prompting Judge James Morrison to revoke her probation and mandate her time at Taycheedah Correctional Institution.
Factors Leading to Chelsea O’Donnell’s 2025 Jail Sentence
A series of infractions throughout 2025 sealed Chelsea’s fate. She spent part of April in jail due to rule violations, encountered medication issues in June that required her to recite written policies, and received citations for dishonesty in July.
In August, she was required to perform community service due to work suspensions, while September led to a two-week jail sentence alongside an essay appealing for another chance. The court documented her challenges comprehensively before ultimately mandating termination from the drug court and activating her prison sentence.
Facts on the Probation Revocation of Rosie O’Donnell’s Daughter
Rosie O’Donnell has consistently expressed her support for her daughter through various legal challenges, recently posting a childhood image on Instagram with a request for prayers. The comedian, who relocated to Ireland earlier this year, told Us Weekly that her daughter is on a “difficult journey,” but the family remains loving and supportive.
Chelsea has been in custody since September 9 and will be transferred to a medium-security facility in Fond du Lac, Wisconsin, to serve her undisclosed sentence.