What happened to Rosie O’Donnell’s first wife Kelli Carpenter? Chelsea O’Donnell’s mom’s whereabouts explored amid prison sentence

American comedian and talk show host Rosie O'Donnell's troubled daughter, Chelsea O'Donnell, who has had a history of drug abuse, was recently sentenced to prison after violating probation terms related to a 2024 drug case. Amid the news of Chelsea's prison sentence, the netizens became curious about Rosie O'Donnell's first wife, Kelli Carpenter.

Rosie O'Donnell, who is also an actress and has starred in movies such as The Flintstones, Now and Then, and Sleepless in Seattle, married Kelli Carpenter in 2004. As per reports, Rosie, who hosted an extremely popular talk show at the time, which ran from 1996 to 2002, split from Kelli in 2007, but she officially broke the news later in 2009. As the netizens are wondering what happened to Kelli Carpenter, she remarried following her split from Rosie.

Kelli Carpenter, who is the co-founder of R-Family Vacations, now rebranded as KelliGregg Travels, is a travel company specifically meant for LGBTQ+ families. The 58-year-old Carpenter is currently married to Anne Steele, a cabaret singer. Kelli Carpenter and Steele tied the knot in 2013 in New York City.

While Carpenter remarried, she continued to co-parent their children along with Rosie O'Donnell. According to People, as cited by Nicki Swift, Rosie adopted her first kid, Parker, as a single parent in 1995. After she got married to Kelli, they adopted their second baby, Chelsea, who was born in 1997. The former couple adopted their third kid, Blake, in 1999, followed by their fourth baby, Vivienne, who was born in 2002.

Rosie O'Donnell and Kelli Carpenter's daughter, Chelsea to serve time in prison

According to Page Six, Rosie and Kelli's 28-year-old daughter, Chelsea, has been ordered by a Wisconsin judge to serve time in prison after violating her probation on October 22, 2025. The Marinette County Treatment Drug Court Team informed US Weekly that Chelsea was also accused of sexual assault. The officials stated that she showed very little improvement in the treatment drug program. Reported by US Weekly, a filing regarding the matter stated:

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"The facts surrounding this request have been staffed with the Marinette County Treatment Drug Court Team and have been deemed sufficient grounds to warrant termination from the Marinette County Treatment Drug Court Program."

While it has not been confirmed yet for how long Chelsea will have to serve time in prison, her mother, Rosie O'Donnell, shared a picture of her and Chelsea on Instagram, asking for people's prayers. This is not the first time Chelsea has been in trouble with the law. In 2024, she was arrested three times, for various reasons, including domestic disputes and drug-related issues. Following her several arrests, Rosie's second oldest, Chelsea, was given six years of probation.

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