The Relationship Journey of Rosie O’Donnell and Her Daughter Chelsea: Ups and Downs
Rosie O’Donnell has openly shared the struggles her daughter Chelsea O’Donnell has encountered over the years.
Following Chelsea’s third arrest in November 2024 within a span of three months, Rosie took to Instagram to discuss her daughter’s legal issues.
“Yes, it’s true – after being bailed out by her biological mother – Chelsea was arrested again and is facing multiple charges connected to her drug addiction – we all hope she can find the support necessary to change her life – #drug-addiction #tragic #sadness #truth,” the comedian commented alongside a screenshot of an email from Fox News seeking her input on the situation.
Rosie and her then-wife Kelli Carpenter adopted Chelsea, who was born in 1997, when she was a baby. Rosie is also the adoptive mother of sons Parker, born in 1995, Blake, born in 1999, and daughters Vivienne, born in 2002, and Dakota, born in 2013.
Continue reading to explore the ups and downs of Rosie and Chelsea’s relationship.
August 2015
Rosie took to X, previously known as Twitter, to report that Chelsea, then 17, had gone missing from their home in Nyack, New York. Cindi Berger, a spokesperson for Rosie, stated to CNN that Chelsea had left with her therapy dog and was “in need of medical attention.”
“Chelsea, like many individuals, faces mental illness,” the statement continued.
One week later, Chelsea was located at the residence of 25-year-old Steven Sheerer in Barnegat Light, New Jersey. Sheerer was subsequently arrested on charges related to distribution of obscenity to a minor and endangering a child’s welfare after authorities discovered “inappropriate communications” between him and Chelsea on her phone. The case was dismissed in April 2018.
After weeks of being away, Chelsea turned 18 and left home once again to reconnect with her birth mother, Deanna Micoley.
“Chelsea chose to go to her birth mother when she turned 18,” Berger explained in a statement at that time. “This was her decision.”
October 2015
During a detailed interview on Inside Edition, Chelsea asserted that her departure from the family home was not a runaway incident, but a result of Rosie evicting her.
“She became very upset with me because I wouldn’t share details about my life and relationships,” Chelsea alleged. She indicated that their relationship had been tumultuous since Rosie’s divorce from Carpenter in 2007.
“I found that really upsetting, which led me to become very depressed and unmotivated,” Chelsea reflected on her moms’ separation. She also mentioned that it was distressing for her when Rosie publicly acknowledged Chelsea’s struggles with mental health.
“Those close to me know I’m neither mentally ill nor unstable; I am quite normal,” Chelsea stated. “I don’t miss Rosie at all.”
Following her initial interview on Inside Edition, Chelsea alleged in November 2015 that Rosie texted her “life is better with you gone.”
March 2017
In another interview with Inside Edition, Chelsea revealed that Rosie was “shocked” to learn about her secret marriage to Nicholas Alliegro in 2016. Chelsea noted that, although they temporarily reconciled in the summer of 2016, they later had a significant argument and became estranged once more.
“Our last argument involved a lot of yelling, and I eventually left the room,” Chelsea shared.
2018
Later, Chelsea ended her relationship with Alliegro and welcomed her daughter Skylar with then-boyfriend Jacob Bourassa in December 2018. She repaired her relationship with Rosie during her pregnancy.
“Yes, she is expecting. We have reconnected,” Rosie informed People through her representative in June 2018.
In September that year, Rosie shared insights about her bond with Chelsea on an episode of The Talk.
“She’s improving now, and we’re in touch with each other,” Rosie remarked. “When someone does something unforgivable and you both find the capacity to forgive each other, a certain grace envelops both of you.”
Chelsea later welcomed daughters Riley and Avery in 2021 and 2022, and son Atlas in 2023.
September 2024
Chelsea faced felony child neglect and drug possession charges after an arrest in Wisconsin’s Marinette County. Chelsea pleaded not guilty. Following her release on a $2,000 bond, she faced further charges in October 2024 related to drug offenses and bail-jumping. Rosie voiced her thoughts on Instagram, posting a nostalgic photo of Chelsea with one of her newborn children.
“Chelsea is in the headlines today – here’s a throwback to better times – unfortunately, this is not new for our family – Chelsea has battled drug addiction for a decade – we all hope she finds a way to overcome this life-threatening illness #💔 #love #alanon,” Rosie captioned the October 2024 Instagram post.
Prior to being bailed out by Micoley, Chelsea lashed out at Rosie from behind bars.
“My mother cares more about freeing the Menendez Brothers than about getting me released,” she alleged during a November 2024 interview with the Daily Mail. “When I asked Rosie to bail me out, she bluntly said, ‘You belong in there.’ She told me, ‘I can’t be responsible for you dying; I don’t want that weight on my conscience.’”
November 2024
While out on bail, Chelsea was arrested for the third time in three months. The incident occurred when she was a passenger in a vehicle pulled over for excessive noise, according to a police report acquired by Us Weekly. A background check revealed that Chelsea was out on bail for prior drug cases, and she was previously instructed to “maintain absolute sobriety” while on bail.
Chelsea remains in custody, with her next court appearance set for December 2024.
Rosie expressed her feelings about her daughter’s third arrest through Instagram in December 2024, stating that “we all hope she finds the help necessary to turn her life around.”
April 2025
Chelsea filed for a legal name change, according to court records reviewed by Us at the time. In response, Rosie shared a poem titled “My Daughter Chelsea” via her Substack page.
The poem, which Rosie obtained permission to share publicly from Chelsea, reflected on Chelsea’s past legal issues and substance abuse struggles while noting that Chelsea wanted to adopt “her birth mother’s maiden name.” Although Rosie expressed that the decision was puzzling to her, she affirmed her support for Chelsea.
If you or someone you know is struggling with substance abuse, please contact the Substance Abuse and Mental Health Services Administration (SAMHSA) National Helpline at 1-800-662-HELP (4357).
