Rosie O’Donnell shares text message with jailed daughter after reconciliation

Kathleen PerriconeFri, August 28, 2026 at 1:15 AM UTC

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Rosie O’Donnell and her daughter ChelseaCredit: Raymond Hall/GC Images; Rosie O'Donnell/InstagramKey Points -

Rosie O’Donnell shares a personal text message with her daughter Chelsea, who is serving an 18-month prison sentence.

In the conversation, the two chat about manicures and books.

O’Donnell recently revealed she visited Chelsea in jail and it was their most “consistent” conversation in a decade.

As Rosie O’Donnell works on rebuilding her relationship with her incarcerated daughter Chelsea, she’s giving a glimpse into their daily catch-ups.

The TV personality shared a personal text message between them with her 1.4 million Instagram followers on Thursday, as the 28-year-old prepares for release from jail.

Rosie O’Donnell’s texts with her daughter ChelseaCredit: Rosie O'Donnell/Instagram

“Thank you mom I got my music back today. How are you?” wrote Chelsea, who is currently serving an 18-month sentence at Taycheedah Correctional Institution in Wisconsin. “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.”

O’Donnell responds with enthusiasm to the update and reveals to her daughter that she just got a manicure. However, “no more gel for me my nails are ruined,” she added.“Are u reading a good book ?”

“I am reading the legacy series,” replied Chelsea, referencing the adult dark fantasy four-book collection by Melissa K. Roehrich. “Its [sic] really good she has a bunch of other books too. And yeah I havnt [sic] painted my nails in years but I remember that stuff breaking my nails.”

Rosie O’Donnell visiting her daughter Chelsea in jailCredit: Rosie O’Donnell/Instagram

O’Donnell’s Instagram post also included a photo with Chelsea, a mother of four, when she visited her daughter in jail back in June.

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The four hours they spent together “was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes,” O’Donnell revealed to Page Six last month.

Chelsea, whom the actress adopted as a baby with her then-wife Kelli Carpenter, ran away from home at 17 and later moved to Wisconsin to live with her birth mother. She reconnected with O’Donnell in 2018 while pregnant with her first child.

Rosie and Chelsea O’Donnell in 2016Credit: Bruce Glikas/FilmMagic

Over the years since, Chelsea struggled with addiction. She was arrested three times in 2024 on multiple drug charges, and in October 2025 her probation was revoked, resulting in an 18-month prison sentence.

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Following their jailhouse visit, O’Donnell wrote about the emotional reunion on her Substack. She noted that her daughter appeared “healthy” and “calm” with “rested blue eyes” and “clear skin” when she walked in the room. They then embraced and there were “shy smiles all around.”

Since her visit, O’Donnell continued, Chelsea “calls daily” and the two have “gotten closer” amid the “tense times” of her incarceration. “I’m grateful for that,” she admitted. “That she’s alive/Looking forward to her release/Planning her post prison journey /Drug free.”

on Entertainment Weekly

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Source: “AOL Entertainment”