Rosie O’Donnell says there is one longtime friend who remains an exception to the political divide she otherwise finds difficult to overlook, country star Wynonna Judd.
During the Aug. 3 episode of The Tangle with Kyle Ridley, O’Donnell was asked whether she still tries to find common ground with people who support President Donald Trump or has removed them from her life. She said she does not really have people close to her who support him before naming Judd as the exception.
“I am friends with Wynonna Judd, who I love very much,” O’Donnell said, adding that the two have known each other for many years. O’Donnell described Judd as a Trump supporter but said that despite their political differences, “somehow, we never bring it up.”
It was not the first time O’Donnell had publicly described their friendship that way. As TheWrap reported, she made a similar point in 2024, saying their opposing political views had not damaged a friendship spanning approximately three decades.
O’Donnell Says She and Judd Simply Don’t Discuss Trump
O’Donnell told Ridley that Judd receives a degree of understanding from her that she does not necessarily extend to other Trump supporters. “I kind of give her a grace in a way,” O’Donnell said.
She pointed to difficult experiences in Judd’s life, including the 2022 death of her mother and longtime musical partner, Naomi Judd, as part of why she is able to put their political differences aside when they interact. O’Donnell emphasized that her affection for Judd remains intact even though she strongly disagrees with the politics she attributes to her.
Outside that friendship, O’Donnell said she could not think of anyone else close to her who supports Trump. She then sharply criticized the president and explained why she has difficulty understanding people who continue to back him.
Their Friendship Has Survived the Same Divide Before
O’Donnell and Judd knew each other long before Trump’s presidency became a point of political disagreement between them. Their friendship dates back roughly 30 years, including the era of The Rosie O’Donnell Show. The two were also photographed together at O’Donnell’s For All Kids Foundation White Rose Awards in New York in 2002.
In a 2024 TikTok recalled by TheWrap, O’Donnell said people had repeatedly reminded her that Judd supported Trump. “I just love her,” O’Donnell said at the time.
She said their political beliefs were “the polar opposite” of each other but that the difference had not affected their friendship in 30 years. O’Donnell used the relationship as an example of people maintaining affection and respect despite political disagreement. O’Donnell has previously recalled parenting advice Judd gave her, including during an appearance on Tig Notaro’s Don’t Ask Tig.
Judd Worked With Trump’s White House on Criminal Justice Reform
Judd does have a documented history of dealing with the Trump White House, although those meetings centered on criminal justice reform. In 2019, Judd worked with the nonprofit Hope for Prisoners as she advocated for programs designed to help people successfully reenter society after incarceration.
A Hope for Prisoners account of the meetings said Judd met with Brooke Rollins of the White House Office of American Innovation to discuss criminal justice reform, reentry programs and efforts to reduce recidivism. She also spoke with Jared Kushner and Kellyanne Conway during the visit.
A source familiar with the meeting described it at the time as largely introductory, while Hope for Prisoners founder Jon Ponder said Judd was deeply involved in the organization’s work. Judd attended a National Day of Prayer event at the White House during the same trip, where Trump acknowledged her from the podium.
Her advocacy had a personal dimension. Judd’s daughter, Grace Pauline Kelley, had been incarcerated, and the singer said she wanted to use her visibility to advocate for people who felt forgotten.
O’Donnell Made the Same Point About Judd in 2024
In 2024, she explicitly pushed back against the idea that political disagreement automatically required their relationship to end. She said she knew how people characterized Judd’s politics and still loved her. “We have different political beliefs,” O’Donnell said at the time, adding that the difference had never affected their decades-long friendship.
O’Donnell said she has largely surrounded herself with people who share her opposition to Trump, while the friendship with Judd continues without the two making presidential politics a regular subject between them.
Entertainment Weekly said it reached out to Judd’s representatives for comment on O’Donnell’s latest characterization but had not reported a response.