Rosie O'Donnell's Daughter's Return To Jail Involved Disturbing Incident With A Man

Rosie O'Donnell's daughter really went overboard with this one!

Chelsea O'Donnell, who was involved in a slew of back-to-back arrests in 2024, was thrown in jail on an even more controversial allegation of sexual harassment last year, and the records are out to tell what really went down.

Rosie O'Donnell's daughter, Chelsea O'Donnell, apart from her numerous run-ins with the law, also struggles with drug addiction, and her mother has publicly voiced her love and support for her daughter through her struggles.

The comedian's daughter was accused of touching a man's genitals against his will, according to a report written by the State of Wisconsin Department of Corrections. In the report, it was also detailed why Chelsea's probation was terminated towards the end of 2025.

The report noted that the man was in the backseat of Chelsea's car when she reached back and touched his inner thigh. He reportedly pushed her hands away, prompting Chelsea to go further and touch his genitals, while getting upset that the man had turned down her offer.

Chelsea then began to drive carelessly on the road as an expression of her anger, forcing the man to fear for his safety. As reported by TMZ, the comedian's daughter has since denied the allegation, claiming that everything between them was consensual.

Chelsea also got in trouble for failing to obtain permission before engaging in any romantic or sexual relationship. In her admission about the car encounter, she affirmed that she has engaged in sexual relations with four others and even met someone through a dating app.

Between July 2025 and September 2025, the comedian's daughter has reportedly engaged in several sexual relationships, further digging the hole for her probation violation.

The 28-year-old was initially sentenced to 18 months behind bars; however, the sentence was stayed as long as she abides by the given rules, which, according to the officers, has proven difficult for her to do.

Last October, The Blast noted that Chelsea was kicked off the Marinette County Treatment Drug Court Program for failing to take the rehabilitation process seriously and also show signs of improvement.

The comedian reacted to the legal woes of her daughter last year via an Instagram post where she revealed that Chelsea was born into addiction, which makes it very heartbreaking to see her dealing with it.

She vowed to support her through her ordeal but also addressed Chelsea's issue with an iron fist shortly before moving to Ireland to live with her youngest daughter by excluding Chelsea from her $80 million estate.

Rosie adopted Chelsea as her second child after her son Parker when she was just three months old. The 28-year-old was reportedly born dependent on heroin and faced significant medical complications at birth when she was born on September 20, 1997.

Chelsea's woes began from the time she was removed from the drug treatment program, which meant she would serve time for violating the strict terms of her probation. As stated by The Blast, an officer from the Marinette County Sheriff's office noted that she has been in their custody since September 9.

The agent continued that she was sentenced to prison on a Wisconsin judge's order and would be transferred to the Taycheedah Correctional Institution, where she is expected to serve her sentence.

Chelsea received six years of probation last January after three consecutive arrests for drug-related crimes between September and November 2024.

Rosie was one who expressed her intention to relocate out of the United States following President Donald Trump's reelection, and she did follow through by moving to Ireland to be with her daughter.

However, she recently revealed to Chris Cuomo on "SiriusXM's Cuomo Mornings" that she touched base in the United States for a two-week stay because she wanted to know how safe it is for her and her daughter to come visit for the summer.

"I wanted to see how hard it would be for me to get in and out of the country. I wanted to feel what it felt like," she explained.

O'Donnell continued that her absence from the U.S. also created a longing in her heart to visit her children, whom she has not seen in over a year since she left the country last January with her 13-year-old child, Clay.

She continued that she does not regret her decision, as the energy she felt in the United States was scary and life in Ireland is a calmer alternative to the intensity and media pressure in the U.S. O'Donnell affirmed that she made the move to preserve her and her child's life and her sanity.

What is next for Rosie O'Donnell's daughter?