Rosie O’Donnell shares text message from incarcerated and estranged daughter Chelsea O'Donnell

The Flintstones actress-turned-comedian Rosie O'Donnell drew attention online after she took to her official Instagram handle and shared a screenshot of a text message between her and her adopted daughter, Chelsea, who was imprisoned in October 2025.

According to Entertainment Weekly, Chelsea, 28, whom Rosie O'Donnell adopted as a baby in 1997, had a history of drug addiction and a drinking problem. A mother to four kids, Chelsea has often gotten herself into trouble with the law and was taken into custody thrice in 2024, after which her probation was cancelled, leading to 18 months in prison in Wisconsin's Taycheeda Correctional Institution.

While Rosie O'Donnell's daughter, Chelsea, serves her time in prison, the Exit to Eden star is putting in effort to repair her relationship with her imprisoned daughter. O'Donnell, along with a picture of herself with Chelsea, shared a screenshot of a personal text message between the two, in which they could be seen engaging in a candid, light-hearted conversation. Their conversation began with Chelsea writing:

"Thank you mom I got my music back today. How are you? 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."

To which Rosie enthusiastically responded:

"Ok great - got my nails done - no more gel for me my nails are ruined. Are you reading a good book?"

After which Chelsea replied:

"I am reading the legacy series. 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."

Check out Rosie O'Donnell's August 27, 2026, Instagram post below:

Rosie O'Donnell had her first conversation with Chelsea in ten years in prison

Another Stakeout actress, Rosie O'Donnell, during a July 2026 interview with Page Six revealed that her first conversation with her daughter Chelsea after a decade was in prison, when she went to visit her there. O'Donnell said:

It "was the first conversation I’ve had with her in 10 years that lasted more than 25 minutes."

She further added:

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"The first time that I saw her in a consistent way was the four hours in the prison. And that’s the first time I’ve seen, kind of, an empathetic emotion from her."

While speaking to Page Six, O'Donnell also shared that Chelsea began to cry when their visiting time was cut short due to a tornado warning in the area.

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