Rosie O'Donnell and Daughter Chelsea O'Donnell's Relationship Ups and Downs

Rosie O’Donnell hasn’t shied away from publicly discussing the challenges her daughter Chelsea O’Donnell has faced over the years.

After Chelsea was arrested in November 2024 for the third time in as many months, Rosie took to Instagram to address her daughter’s legal troubles.

“So yes this is true – after being bailed out by her birth mother – chelsea was arrested again – and is facing many charges related to her drug addiction – we all hope she is able to get the help she needs to turn her life around – #drug -addiction #tragic #tragic #sadness #truth,” the comedian wrote alongside a screenshot of an email from Fox News reaching out to her for comment on the matter.

Rosie and her then-wife Kelli Carpenter adopted Chelsea, who was born in 1997, as an infant. She is also an adoptive mom to sons Parker, born in 1995, Blake, born in 1999, and daughters Vivienne, born in 2002, and Dakota, born in 2013.

Rosie O’Donnell’s Daughter Chelsea Released After Criticizing Star in Jail

Keep scrolling to learn more about Rosie and Chelsea’s relationship ups and downs.

August 2015

Rosie took to X, then called Twitter, to note that Chelsea, who was 17 at the time, had gone missing from their family home in Nyack, New York. Cindi Berger, a spokesperson for Rosie, said in a statement to CNN that Chelsea had run away with her therapy dog and was “in need of medical attention.”

“Chelsea, like millions of people, lives with mental illness,” the statement continued.

One week after going missing, Chelsea was found at 25-year-old Steven Sheerer’s home in Barnegat Light, New Jersey. Sheerer was later arrested on charges of distribution of obscenity to a minor and endangering the welfare of a child after investigators found “inappropriate communications” between him and Chelsea on Chelsea’s phone. The case was dismissed in April 2018.

Weeks after running away, Chelsea turned 18 and left home again, reuniting with her biological mom, Deanna Micoley.

“Chelsea made a decision when she turned 18 that she wanted to go to her birth mother,” Berger explained in a statement at the time. “This was her choice.”

October 2015

During an extensive interview on Inside Edition, Chelsea claimed that her disappearance from her family’s home wasn’t a runaway situation, but the result of Rosie kicking her out.

“She got really upset with me because I wouldn’t talk to her about what was going on with, I guess, my life and relationships and such,” Chelsea alleged. She noted that the mother-daughter duo’s relationship had been strained since Rosie’s 2007 split from Carpenter.

“It was really upsetting for me, so I kind of just got really depressed and didn’t want to do anything,” Chelsea said of her moms’ divorce. She added that it was also “really upsetting” when Rosie publicly declared that Chelsea struggles with mental illness.

Cops Claim Rosie O’Donnell’s Daughter Was ‘Actively Using' Meth Pre-Arrest

“The people who know me and that are close to me know that I’m not, like, mentally ill and crazy and that I’m pretty normal,” Chelsea said. “I don’t miss Rosie at all.”

In a November 2015 Inside Edition update, Chelsea claimed that Rosie had texted her “life is better with u gone” after seeing her initial interview on the show.

March 2017

Chelsea sat down with Inside Edition again and shared that Rosie was “shocked” when she found out she’d secretly married Nicholas Alliegro in 2016. Chelsea added that although she and Rosie temporarily reconciled during the summer of 2016, they’d since had a big fight and were again estranged.

“The last time we got into an argument, we ended up screaming at each other, and I left the room,” Chelsea said.

2018

Chelsea later split from Alliegro and welcomed daughter Skylar with then-boyfriend Jacob Bourassa in December 2018. She mended fences with Rosie during her pregnancy.

“Yes, she is pregnant. We have reconnected,” Rosie told People through her rep in June 2018.

That September, Rosie opened up about her and Chelsea’s relationship during an episode of The Talk.

“She’s doing better now, and we’re both communicating with each other,” Rosie said. “When somebody does something unforgivable to you and you can forgive them and they can forgive you, there’s a kind of grace that descends upon the both of you, within that.”

Chelsea went on to welcome daughters Riley and Avery in 2021 and 2022, respectively, and son Atlas in 2023.

September 2024

Chelsea was arrested on felony child neglect and drug possession charges in Wisconsin’s Marinette County. Chelsea later pleaded not guilty to the charges. After being released on a $2,000 bond, she was charged again in October 2024 with additional felony drug and bail-jumping charges. Rosie reacted to the news via Instagram, sharing a throwback photo of Chelsea holding one of her children as a newborn.

Rosie O’Donnell Speaks Out Following Daughter’s Arrest

“Chelsea is in the news today – this is a photo from a better time – here is the family comment: sadly this is not new for our family – chelsea has struggled with drug addiction for a decade – we r all hopeful she will find her way out of this deadly disease # #love #alanon,” Rosie captioned the October 2024 Instagram post.

Before being bailed out by by Micoley, Chelsea slammed Rosie from behind bars.

“My mother is more interested in getting the Menendez Brothers released from prison than getting me out,” she claimed during a November 2024 interview with the Daily Mail. “When I called Rosie to ask her to bail me out, she told me flat out, ‘You belong in there.’ She said: ‘I really can’t help you get out of there; I don’t want you to kill yourself. I don’t want to be responsible for you killing yourself.’”

November 2024

Chelsea was arrested for the third time in three months while out on bail. The arrest occurred when she was a passenger in a vehicle that was pulled over due to loud exhaust, according to a police report obtained by Us Weekly. After running Chelsea’s information, the police officer discovered that Chelsea was out on bail for previous drug cases. She was previously ordered to “maintain absolute sobriety” while out on bail.

Chelsea remains in custody and her next court date is scheduled for December 2024.

Rosie reacted to her daughter’s third arrest via Instagram in December 2024, noting that “we all hope she is able to get the help she needs to turn her life around.”

April 2025

Chelsea filed to legally change her name according to court records viewed by Us at the time. Rosie, for her part, shared a poem via her substack page titled “My Daughter Chelsea.”

The piece — which Rosie got permission from her daughter to share publicly — touched on Chelsea’s past legal trouble and struggles with substance abuse while noting that Chelsea wanted to change her name to “her birth mom’s maiden name.” While the decision doesn’t “make sense” to Rosie, she expressed her support for Chelsea.

If you or someone you know is struggling with substance abuse, contact the Substance Abuse and Mental Health Services Administration (SAMHSA) National Helpline at 1-800-662-HELP (4357).