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Troubled past of Rosie O'Donnell's daughter Chelsea explained amid prison sentence

Home> Celebrity> News

Updated 15:40 30 Oct 2025 GMTPublished 14:59 30 Oct 2025 GMT

Troubled past of Rosie O'Donnell's daughter Chelsea explained amid prison sentence

Chelsea O'Donnell is set to serve jail time, but her past has been anything but smooth sailing

Joe Yates

Joe Yates

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Featured Image Credit: Bruce Glikas/Bruce Glikas/FilmMagic via Getty Images

Topics: Celebrity, US News

Joe Yates
Joe Yates

Joe is a journalist for UNILAD, who particularly enjoys writing about crime. He has worked in journalism for five years, and has covered everything from murder trials to celeb news.

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After Rosie O'Donnell requested her fans keep her 28-year-old daughter Chelsea in their prayers, her child's run-in with the law has been explained.

The talk show host called on her followers to help her second-eldest of five children after a judge ruled that she had violated the probation she was serving from a sentence she received in March, meaning she'll now serve prison time.

A Wisconsin judge officially revoked Chelsea’s probation last Wednesday (October 22), after court documents said she failed to meet the requirements of the Marinette County Treatment Drug Court Program and was terminated from that program.

The move followed a string of arrests last year and a guilty plea earlier this year to resisting or obstructing an officer, felony bail jumping and possession of methamphetamine - to which she was ordered to serve six years on probation.

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Rosie O’Donnell, 63, reacted publicly on Instagram - sharing a childhood photo of Chelsea and a heartfelt caption: "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."

Chelsea O'Donnell will serve jail time (Marinette County Sheriff's Office)
Chelsea O'Donnell will serve jail time (Marinette County Sheriff's Office)

While also sharing the following statement with People: "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."

Chelsea was adopted by O'Donnell in 1997 and one of five children in the family, and has gone on to have four kids of her own - but her love life has been a bit of a rollercoaster.

While it’s not clear who she’s dating right now, her most public relationship was with ex-boyfriend Jacob Bourassa - who’s also the dad of three of her four kids.

Chelsea O'Donnell, with sister Vivienne O'Donnell and mom Rosie O'Donnell, back in 2016 (Bruce Glikas/Bruce Glikas/FilmMagic)
Chelsea O'Donnell, with sister Vivienne O'Donnell and mom Rosie O'Donnell, back in 2016 (Bruce Glikas/Bruce Glikas/FilmMagic)

The pair got together back in 2018 - around the same time her divorce was playing out with her ex-husband Nick Alliegro - and welcomed daughters Skylar Rose, Riley, and Avery Lynn.

But their public breakup led to Bourassa being granted custody of their children in 2019.

Chelsea moved on however, welcoming a baby boy named Atlas with another partner, Jacob Nelund - who she was with last year when she was arrested on her most recent conviction following a domestic dispute at their Wisconsin home.

Rosie O'Donnell and her daughter Chelsea, pictured back in 2006 (M. Von Holden/Getty Images)
Rosie O'Donnell and her daughter Chelsea, pictured back in 2006 (M. Von Holden/Getty Images)

Police allegedly found drug paraphernalia and syringes during the incident.

Bourassa then filed to change the custody deal she has with their children to prevent her from having unsupervised visits with their children.

Now, court records state that the reason for her probation being terminated is due to her having showed 'minimal advancement' in treatment, and new allegations prompted the team to recommend termination and the judge to cancel probation.

Local reports say Chelsea has been in custody since early September and has now been transferred to a medium-security correctional facility in Wisconsin.

The exact length of her sentence has not been publicly confirmed.

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