Rosie O'Donnell shares text messages from jailed daughter as the pair reconcile after 10 years
Rosie O'Donnell has shared a look at her renewed relationship with her daughter Chelsea, who is currently serving an 18-month sentence in Wisconsin.
The pair has been estranged for over a decade, but the messages show there is hope of reconciliation.
The comedian, 64, posted a throwback photograph of herself and Chelsea, 28, on Instagram, alongside screenshots of their recent messages.
O'Donnell has been attempting to reconnect with her daughter after she previously opened up about the 'scary future' Chelsea was facing.
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The comic is a mother of five, to sons Parker, 30, and Blake, 26, as well as Chelsea, then welcomed daughter Vivienne, 23, through artificial insemination and she later adopted another daughter, Dakota, 12.
In the shared messages, Chelsea starts the conversation by updating her mother on life behind bars and her plans for the future.
Text messages and hope for reconciliation
“Thank you mom I got my music back today. How are you?” Chelsea wrote, before adding that she was trying to contact a social worker about plans for when she is released.
O'Donnell replied with an update of her own, telling her daughter she had recently had her nails done and joking that she would not be having gel manicures again because they had damaged her nails. She then asked Chelsea whether she was reading a good book.
Chelsea said she was reading the Legacy series and agreeing: "Yeah I haven't painted my nails in years but I remember that stuff breaking my nails."
O'Donnell has previously spoken openly about the difficulties in her relationship with Chelsea, including periods when they had little meaningful contact.
The pair's relationship became particularly strained after Chelsea left home as a teenager.
O'Donnell later revealed that her daughter had struggled with addiction, describing her situation as a painful journey for Chelsea.
Chelsea was arrested several times in Wisconsin during 2024.
Among the charges she faced was resisting or obstructing an officer, felony bail jumping and possession of methamphetamine, as well as the illegal obtaining of both prescriptions and drug paraphernalia at the time, along with misdemeanour possession of THC, according to PEOPLE.
She also faced allegations relating to child neglect.
In February 2025, Chelsea pleaded guilty to three felony charges, and she was sentenced to probation with strict conditions.
She was required to stay sober, and to avoid contact with known drug users or sellers.
Prison sentence and a 'scary' future
Sadly, it wasn't long before her probation was revoked after she breached these conditions, and she was sent to prison in October 2025.
She is now serving an 18-month sentence at Taycheedah Correctional Institution in Wisconsin.
Following the revelation that Chelsea would be going to prison, O'Donnell urged people to offer prayers and positive thoughts for her.
She shared a throwback picture of her daughter, and wrote: "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."
The comedian also released a statement to PEOPLE, which said: "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."
But the biggest breakthrough in their relationship came during a prison visit earlier this year.
O'Donnell said the visit marked the first conversation she had shared with Chelsea in around 10 years, that lasted more than 25 minutes.
They spent almost four hours together, although unfortunately their meeting was cut short by a tornado warning.
She later told Page Six "That’s the first time I’ve seen, kind of, an empathetic emotion from her,” when Chelsea cried that the meeting had to come to an end early.
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Jen Thomas