Rosie O'Donnell reveals bittersweet details of recent visit to incarcerated daughter in federal prison

Rosie O'Donnell is opening up about her recent visit to a federal prison to see her daughter Chelsea.

O'Donnell revealed that the meeting was the first time she 'properly' talked to her 28-year-old daughter – whom she adopted as a baby with her ex-wife Kelli Carpenter – in a decade. 

The update comes after she shared a lengthy and deeply personal poem about her prison visit with her daughter last month.

The Daily Mail has reached out to O'Donnell for additional comment but has not yet received a response. 

'[The visit] was the first conversation I've had with her in 10 years that lasted more than 15 minutes,' the 64-year-old actress, comedian and talk-show host told Page Six in an interview published on Sunday. 

Chelsea was ordered to serve prison time in October after her probation was revoked following a string of arrests in 2024, involving multiple felony charges, including child neglect and possession of methamphetamine. 

Chelsea is currently serving an 18-month sentence at the Taycheedah Correctional Institution, a women's maximum-security prison in Fond du Lac, Wisconsin. 

When her daughter was incarcerated late last year, O'Donnell shared a statement and spoke about Chelsea's years-long battle with addiction. 

'I have compassion for those struggling with addiction,' the comedian told Us Weekly at the time. 

'Chelsea was born into addiction and it has been a painful journey for her and her children,' she continued. 'We continue to love and support her through these horrible times. Prayers welcomed.' 

The View alum recalled how her daughter cried at one point during their visit.

She recalled how they shared an emotional moment when inmates and their loved ones were informed visitation hours would be cut short due to bad weather. 

'That's the first time I've seen, kind of, an empathetic emotion from her,' O'Donnell told Page Six. 

'So, you know, she's growing up,' she continued. 'And I hope that her future is brighter than this past decade has been.' 

O'Donnell and her eldest daughter have had a tumultuous relationship over the years and were estranged at various points throughout Chelsea's teenage and early adult years. 

In addition to Chelsea, O'Donnell also shares Parker, 31, Blake, 26, and Vivienne, 23, with ex-wife Carpenter. She welcomed her youngest child Clay, 13, with her late ex-wife Michelle Rounds. 

In March 2017, Chelsea, who was 19 at the time, opened up about her relationship with O'Donnell in an interview with Inside Edition. 

'Growing up, I never really got along with her and then once she kicked me out, I was just kind of done,' she said at the time. 

'I miss the rest of my family a lot but I think there is some much-needed space between me and Rosie. It's been nice having that.' 

The mother-daughter duo later reconnected the following year when Chelsea was pregnant with her first child. 

Chelsea, now a mother of four, was arrested three times between September and November 2024 in Wisconsin on multiple felony charges, including neglecting a child and possession of methamphetamine. 

She was sentenced to six years of probation before later being sent to prison upon allegedly violating the terms of her probation.   

O'Donnell previously took to social media to share a poem she wrote about visiting her daughter in prison. 

In June, she shared a photo of herself and Chelsea embracing and wrote that her daughter looked 'good.'

'I arrive early / It's very hot / I'm wearing shorts / Waiting for her // In what looks like a children's nursery room / Disney murals on cement walls,' she wrote.

'Table 8 – I'm told to sit / In one of the red chairs / Beige is for the inmate,' she continued.

'The guard explained the rules // A hug hello and goodbye only / No money exchanged / Hands above the table / No loud voices // The visit is 4 hours long / There r worn out games to play / Scrabble – cards – chutes & ladders / Other families walk in.' 

She also wrote about Chelsea's visible disappointment after their visit was brought to an early stop due to the weather outside.

'The guard announces we must leave as a tornado has touched down nearby,' she wrote, adding, 'Chelsea slumps in her chair / Crestfallen – we r rushed out / A quick hug / And im back in the car.

'It storms all the way to the hotel. As I try to process. All that's happened. It was a big day for both of us.' 

On the same day as O'Donnell's recent interview, she took to social media to share a photo from her recent visit to another one of her kids - her son Blake and his baby boy Anthony. 

Blake and his wife Teresa welcomed their baby boy Anthony in March earlier this year.

The proud grandmother posted a photo holding her grandson after spending time with her son and his family in New Jersey.

She also shared snapshots of her son, as well as her youngest child, Clay, during a beach outing they enjoyed together at one point.