Rosie O’Donnell offered followers a rare glimpse into her renewed bond with daughter Chelsea on Thursday, posting a photo of the pair together while Chelsea remains behind bars.
The comedian and former talk show host re-established contact with her 28-year-old daughter in June, marking their first reunion after roughly ten years of estrangement.
Alongside the image from that emotional prison visit, O’Donnell also shared a screenshot of recent text messages, showing how the mother and daughter have continued communicating as they work to repair their relationship.
“Thank you mom I got my music back today. How are you?” Chelsea wrote in one of the messages.
She added, “I’m trying to get ahold of the social worker to let her know the plans for when i get out, Hannah texted her for me.”
Chelsea is currently serving an 18-month sentence at Taycheedah Correctional Institution in Wisconsin after her probation was revoked last October, following a series of arrests in 2024.
Rosie O’Donnell posted a photo with her daughter Chelsea, 28, on Thursday, sharing a moment from their June reunion behind bars after a decade apart
The 64-year-old comedian and chat show personality also shared text messages from Chelsea as the pair continue rebuilding their mother-daughter relationship
O’Donnell replied to her daughter’s text positively before talking about the manicure she just got.
She shared: ‘no more gel for me my nails are ruined.’
She then asked Chelsea if she was ‘reading a good book?’
‘I am reading the legacy series,’ Chelsea responded. ‘Its really good she has a bunch of other books too. And yeah I havnt painted my nails in years but I remember that stuff breaking my nails.’
Our News Outlet has reached out to representatives for O’Donnell for further comment on the story.
Chelsea is one of four children whom O’Donnell shares with her ex-wife Kelli Carpenter.
She had a fifth child with ex-wife Michelle Rounds who died in 2017.
Chelsea, a mother of four, is serving an 18-month sentence after her probation was revoked last October following a string of arrests in 2024. Above, Chelsea and O’Donnell in 206
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In March 2025, Chelsea pleaded guilty to felony bail jumping, resisting or obstructing an officer and possession of methamphetamine. She was initially sentenced to probation in March but was later jailed after violating its conditions.
At the time, O’Donnell said she had compassion for those struggling with addiction, adding: ‘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.’
This past July, O’Donnell told PageSix that her June visit with Chelsea ‘was the first conversation I’ve had with her in 10 years that lasted more than 15 minutes.’
She went on: ‘She’s growing up. And I hope that her future is brighter than this past decade has been.’
O’Donnell, 64, returned to the spotlight last week with a guest-hosting gig on ABC’s Jimmy Kimmel Live!
The star, who decamped to Ireland to escape Donald Trump’s America, seemed to relish the opportunity to take some big digs at the president during her late night appearances.
O’Donnell returned to the spotlight last week with a guest-hosting gig on ABC’s Jimmy Kimmel Live!
She is most famous for her titular syndicated daytime talk show, The Rosie O’Donnell Show, which made her a household name after debuting in 1996. It ran until 2002
The native New Yorker started out as a standup comic before winning roles in several Hollywood movies including A League Of Their Own, Sleepless in Seattle and a live-action version of The Flintstones.
In 1996, she debuted her titular syndicated daytime talk show, The Rosie O’Donnell Show, which made her a household name. She won several Daytime Emmy Awards before ending the show in 2002.
O’Donnell then had two separate stints on The View – one that lasted less than a year in 2006, and one that only spanned six months in 2014.
She left the show in February of the following year, for health and personal reasons.
