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Watch: Rosie O’Donnell Says Prison Visit With Daughter Chelsea

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Rosie O’Donnell’s 5 Kids: A Family Guide

Watch: Rosie O’Donnell Says Prison Visit With Daughter Chelsea Was the Longest They’d Spoken in 10 Years

As long as Rosie O’Donnell has her family, she’ll never have to feel like she’s in a league of her own.

And while she and daughter Chelsea O’Donnell have a complicated relationship history—at times being estranged—the former talk show host has given fans a glimpse inside their bond today.

Noting she recently visited Chelsea in prison, Rosie told Page Six the reunion “was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes.”

“The first time that I saw her in a consistent way was the four hours in the prison,” the A League of Their Own actress added in the July 12 interview, sharing that Chelsea cried when they had to part ways earlier than expected due to a tornado warning. “And that’s the first time I’ve seen, kind of, an empathetic emotion from her.”

Chelsea was arrested in Wisconsin three times from September to November 2024 on multiple charges, including drug possession. The 28-year-old was sentenced to prison in October after a judge revoked her probation, according to online records. However, Rosie told Page Six Chelsea has now been sober for nearly two years and is making changes.

“She’s growing up,” she said, “and I hope that her future is brighter than this past decade has been.”

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Rosie O’Donnell Says Prison Visit With Daughter Chelsea Was the Longest They’d Spoken in 10 Years

And no matter what, Chelsea will always be Rosie’s little girl.

“She turns 29 this summer,” Rosie wrote in a June Instagram post. “And all I see when I look at her is a blonde baby in diapers.”

Bruce Glikas/Bruce Glikas/FilmMagic

Chelsea is one of Rosie’s five kids along with Parker, 31, Blake, 26, Vivienne, 23, and Clay, 13. And while the 64-year-old may be a celebrity to the rest of the world, to her children, she’s mom.

“My kids have no interest in my career in any capacity,” Rosie said on The Kelly Clarkson Show in 2023. “They never have.”

To learn more about Rosie’s family, keep reading.

Photo by Slaven Vlasic/Getty Images

Rosie O’DonnellFans of Rosie O’Donnell are sure to remember her eponymous talk show, which premiered in 1996. But after a successful six-year run, she left to spend more time with her children.”I wanted to be at their softball games,” she told Page Six in July 2026, noting she quit with $100 million in the bank. “I wanted to be at school plays.”In addition to being a talk show star—also cohosting The View for several years—Rosie is an actress who’s appeared in movies like A League of Their Own, The Flintstones and Disney’s animated film Tarzan.Rosie has been married twice. She wed Kelli Carpenter in 2004 before they broke up in 2007. Rosie then tied the knot with Michelle Rounds, but they split in 2015. Michelle died in 2017.

Instagram / Rosie O’Donnell

Parker Jaren O’DonnellBorn in June 1995, son Parker was adopted by Rosie when he was a baby. After graduating from Valley Forge Military Academy for high school, he attended The Citadel. Parker then served in the U.S. Marine Corps for four years before pursuing a new career.”He’s working at a gaming business where he makes the Warhammer models,” Rosie told Entertainment Tonight in 2023. “And he’s loved that since he was a little kid.”And whatever’s next, Parker will always have Rosie’s support.”Im proud of him Of all he has done To find where he wants to be who and what makes him happy,” she wrote in a June 2026 Substack post for his 31st birthday. “I could not love u more PJOD – its impossible.”

Instagram / Rosie O’Donnell

Chelsea Belle O’DonnellRosie and Kelli adopted daughter Chelsea Belle O’Donnell after her birth in August 1997.Over the years, Chelsea has made headlines for her complicated relationship with Rosie—including periods of estrangement—and her personal life. In August 2015, Rosie announced her then-17-year-old daughter was missing. Chelsea was found a week later. The following year, she eloped with Nick Alliegro. However, she filed for divorce in 2018.That same year, Chelsea and boyfriend Jacob Bourassa welcomed daughter Skylar Rose, Rosie’s first grandchild. The pair went on to welcome daughter Riley in 2021, daughter Avery Lynn in 2022 and son Atlas in 2023.Chelsea was arrested in Wisconsin three times from September to November 2024 on multiple charges, including drug possession. She was sentenced to prison in October 2025 after a judge revoked her probation, according to online records.Rosie has opened up about Chelsea’s sobriety journey and visiting her in prison.”She’s growing up,” Rosie told Page Six in July 2026, “and I hope that her future is brighter than this past decade has been.”

Instagram / Rosie O’Donnell

Blake Christopher O’DonnellRosie and Kelli grew their family by adopting son Blake, a.k.a. “Blakey,” after he was born in December 1999.He started dating his high school sweetheart Teresa Garofalow Westervelt in 2016 after sliding into her DMs. The Marist University alum then proposed to his longtime love at a Broadway performance of The Phantom of the Opera in 2022, and they tied the knot two years later.Blake and Teresa became parents when they welcomed son Anthony Joel in March 2026.

Instagram / Rosie O’Donnell

Vivienne Rose O’DonnellIn November 2002, Kelli gave birth to Vivienne Rose—with Rosie’s rep telling People at the time their daughter was named after the main character in Divine Secrets of the Ya-Ya Sisterhood as well as Rosie’s late mother Roseann.After graduating from the University of Delaware in 2025, Vivienne—a.k.a. Vivi—moved to New York, where she often posts about her life with dog Ziggy on social media.

Instagram / Rosie O’Donnell

Clay O’DonnellBorn in January 2013, Clay was adopted by Rosie and Michelle. Over the years, fans have gotten glimpses into Rosie and Clay’s world on social media and in the 2025 documentary Unleashing Hope: The Power of Service Dogs for Children With Autism (Clay was diagnosed at age 2). In 2025, Rosie and Clay moved to Ireland.”There’s a great, great school there. And Clay has done very well,” Rosie told Us Weekly that April. “And they were really welcoming.”

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