Rosie O'Donnell's Daughter's Prison Lifestyle Revealed

Rosie O'Donnell's troubled daughter is counting down the days to her transfer to a state prison.

The TV personality's adopted daughter, Chelsea O'Donnell, whose life has been plagued by legal troubles, is set to be moved to a new facility to serve out her prison sentence.

So far, Rosie O'Donnell's daughter has been living behind bars at a Wisconsin jail, with accommodations that are closer to heaven on earth than what she might endure in a state prison.

The Wisconsin jail Chelsea has been living in since violating the terms of her probation is reportedly filled with cozy accommodations for inmates. Marinette County Assistant Jail Administrator Jake Roberts shed more light on the situation, revealing Rosie's adopted daughter is housed with the general population.

Inmates at the facility typically had roommates; however, they were allowed to spend more time outside their cells. Roberts explained that they had dayroom time in a shared common area where they could play games such as Phase 1, Uno, chess, and checkers.

Additionally, Roberts told TMZ that inmates enjoyed tasty meals at the facility, including chicken patties, tacos, pizza, and rice. Inmates like Chelsea could also watch cable TV and were connected to the outside world through phone privileges, video visits, and a kiosk for sending messages.

Following three back-to-back arrests for drug-related crimes from September to November 2024, Rosie's daughter was sentenced to six years of probation. It was reported that Chelsea was re-arrested for a probation violation.

Court records revealed that a Wisconsin judge had sentenced Chelsea to prison on Wednesday, October 22, for violating the terms of her probation. She allegedly did so after sexual assault claims were leveled against her; however, details about the incident weren't recorded.

An official from the treatment drug court also accused Chelsea of failing to take her rehabilitation program seriously. They stressed that she had not shown significant improvement, thereby leading to her termination from the Marinette County Treatment Drug Court Program.

Rosie addressed Chelsea's legal troubles in an Instagram post, asking for prayers. She shared a throwback picture of her adopted daughter as a child, noting in the caption how happy she was before her life became plagued by addictions.

"I loved her then. I love her now as she faces a scary future," Rosie wrote. She echoed similar sentiments in a statement, noting that her heart went out to everyone struggling with addiction. She revealed that Chelsea was born into addiction and vowed to keep loving and supporting her through her ordeals.

Although she sympathized with Chelsea's situation, Rosie was not one to give too many chances. Before relocating to Ireland with her youngest daughter, Clay, the entertainer reportedly removed Chelsea's name from her $80 million estate.

Following her third arrest in 2024, Rosie's daughter attempted to get a furlough from the $7,500 cash bail set by a Wisconsin judge. The Blast reported that Chelsea pleaded for the exemption to join the AODA treatment for her drug problems.

Chelsea's lawyer pleaded her case, imploring the court to allow her to join the treatment program as soon as possible, but their pleas did not move the judge. The furlough request was denied the following day, keeping Rosie's daughter behind bars.

The repeat offender was arrested a third time in November 2024 for felony possession of methamphetamine, misdemeanor resisting an officer, and more. Her second arrest occurred in October during a traffic stop, where officers found drugs and meth in Chelsea's possession.

A month before her second arrest, Chelsea was taken into custody for child neglect and drug-related charges. Officers had responded to a call at her shared home with her boyfriend, Jacob Nelund, only to uncover their terrifying living conditions.

The police report noted that there was trash, used needles, and all manner of filth lying around. The worst part was finding the couple's young son in a bedroom with drugs, including a meth pipe. An officer claimed the situation was so bad he wanted to throw up.

The Blast shared that Rosie responded to a query about Chelsea's third arrest on Instagram, revealing her daughter's birth mother had bailed her out after her second arrest. Rosie concluded her message with the hope that Chelsea would receive the support she needed.

Will Rosie O'Donnell help her adopted daughter through her latest legal ordeal?