Rosie O'Donnell's Troubled Daughter Chelsea Sentenced to Prison After Drug Probation Violation — as Comic Begs Fans for 'Prayers' During 'Scary' Time
Rosie O'Donnell said she has 'compassion for those struggling with addiction.'
Oct. 29 2025, Published 12:48 p.m. ET
Rosie O'Donnell has spoken out and is begging for prayers after her daughter, Chelsea, was sentenced to time in the slammer, RadarOnline.com can reveal.
Chelsea, 28, was given a prison sentence after violating her probation in a drug case.
What Did Rosie O'Donnell Say About Daughter Chelsea's Jail Sentence?
Rosie O'Donnell called the times she's going through 'horrible' after her daughter's prison sentence.
When speaking to a media outlet about the sad outcome, Rosie shared, "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," she added. "Prayers welcomed."
On October 22, court records indicate a Wisconsin judge decided she'd violated her probation. The violation was due to sexual assault allegations, with no further details revealed.
Chelsea Did Not Show Progress in Her Treatment Program
Rosie O'Donnell's daughter's lack of progress in her treatment program got her terminated from it.
Aside from the sexual assault allegations, an official insisted Chelsea has not shown progress in the treatment program.
"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 said.
On October 27, an officer at the Marinette County Sheriff’s Office told a media outlet Chelsea had been in custody since September 9 and confirmed she was sentenced to prison.
They noted Chelsea is due to be transferred to the Taycheedah Correctional Institution, which is a medium-security prison in Wisconsin. She will serve her sentence at that facility or be moved to another prison. However, they interestingly would not confirm her sentence.
Chelsea's Probation Charge Explained
Chelsea O'Donnell was sentenced to six years' probation after three back-to-back arrests.
In January 2025, Chelsea was sentenced to six years' probation after she had three back-to-back arrests – first on September 10, 2024, on charges of drug possession and child neglect, then on October 11, 2024, over drugs, and then on November 18, 2024, also over drugs.
Chelsea had reached a plea deal with prosecutors based on the three arrests, where she pleaded guilty to certain charges and had other charges dropped.
As part of the plea deal, the court sentenced her to 18 months in prison, but they "stayed" the sentence, allowing her to only serve probation as long as she didn't get into trouble for six years on probation.
The judge insisted she was to have “strict compliance” with the treatment drug court and had to stay sober. In the same vein, she was not allowed to possess or consume alcohol, controlled substances, or any other substances.
Chelsea's Run-Ins With the Law Before Going to Prison
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Rosie O'Donnell's daughter had many run-ins with the law and was given many chances before being put behind bars.
In the months leading up to her going away, Chelsea's had some run-ins with the law.
She served a few days in a county jail in April for violating court rules, but she was allowed to stay on probation at the time.
In June, she ended up in court for a "medication violation," and the court had her write out the "medication policy" and recite it to them.
While she was praised for "positive progress in June," things went south again in July when she had to appear in court due to "dishonesty." She was ordered to write an apology letter to her landlord and go back to phase two of her treatment program.
In August, the court said she was making progress, but they still had "concerns."
In September, she had another bad situation when she was ordered to spend two weeks in a county jail. She was required to write an essay explaining why she should be given one last chance.
Unfortunately, for Chelsea, it seems her chances finally ran out, and she will now have to serve her time behind bars.
