Why Rosie O’Donnell’s Daughter Is Behind Bars — And When Chelsea Could Walk Free

Rosie O'Donnell's adopted daughter, Chelsea O'Donnell, is back in court trouble and, this time, headed to prison. The short version: probation got revoked after fresh allegations and missed rehab progress, and now a previously paused prison term is kicking in. The details are a lot, so let's break it down clearly.

Where things stand

Earlier this year, Chelsea, 28, was given six years of probation after a string of drug-related arrests. That probation has now been revoked. A court official told Us Weekly that the violation involves sexual assault allegations. On October 27, a Marinette County officer said she will be transferred to Taycheedah Correctional Institution, a medium-security women's prison in Wisconsin. She may serve her time there or get moved elsewhere, but the official could not confirm the exact term she will serve.

The legal timeline, simplified

• January 30: Chelsea pleaded guilty in Marinette County to multiple charges, including resisting or obstructing an officer, possessing methamphetamine, bail jumping, maintaining a drug trafficking place as a party to a crime, and possessing an illegally obtained prescription.
• The charges came from two separate cases, dating back to September and November 2024.
• As part of those cases, she was sentenced to probation in both.
• When granting probation, Marinette County Circuit Court Judge James Morrison imposed and stayed a sentence of 1 year in prison plus 1 year of extended supervision. That means the prison time would be held back as long as she followed the rules.
• October 22: Probation revoked in the case tied to meth possession, resisting an officer, and bail jumping. According to the Green Bay Press-Gazette, that stayed sentence now goes into effect.
• Separately, court officials say she was terminated from the Marinette County Treatment Drug Court Program for not taking rehab seriously and showing little progress.

Where she is headed

Per the Marinette County officer, Chelsea is being transferred to Taycheedah Correctional Institution. It's Wisconsin's main women's facility, medium security. She could serve her time there or be moved to another prison. Again, the precise length she'll serve has not been confirmed by officials, even though the previously stayed 1-year prison term is now in play on paper.

What jail has looked like so far

TMZ spoke with Marinette County Assistant Jail Administrator Jake Roberts, who said Chelsea has been in general population at the county jail. That means dayroom access from 6 AM to 10 PM, with common-area time outside the cells.

The amenities are surprisingly robust for county lockup: meals like chicken patties, tacos, pizza, and rice; board and card games (including something listed as 'Phase 1' alongside Uno, chess, and checkers — if that sounds off to you, same); cable TV with channels like ESPN, FX, and Hallmark; phones on the wall; a kiosk for messages; and video visits. She can have visitors, and she likely has a cellmate.

Rosie speaks out

Rosie adopted Chelsea in 1997 with then-partner Kelli Carpenter. As the legal situation escalated this month, she asked for prayers on Instagram, sharing a throwback photo of Chelsea as a kid from the 2006 Salute to Women in Sports Awards Dinner.

'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- #addiction awareness #love #family'

Rosie also gave a statement to People, noting that Chelsea has four young children and has struggled with addiction for a long time.

'I have compassion for those struggling with addiction — Chelsea was born into addiction, and it has been a painful journey for her and her four young children. We continue to love and support her through these horrible times. Prayers welcomed.'

Big picture

This is a tough, messy situation: a revoked probation, a transfer to state prison, and a rehab program that ended badly. On the books, that previously stayed 1-year prison sentence plus 1 year of extended supervision is supposed to kick in; in practice, officials still would not confirm the exact term as she heads to Taycheedah. I will update when that becomes clear.