Rosie O'Donnell, a prominent critic of former President Donald Trump, revealed that she maintains a friendship with country music star Wynonna Judd, who she identifies as a Trump supporter. O'Donnell stated that Judd is the only person in her life who supports the former president.

"I am friends with Wynonna Judd, who I love very much, and I've known her for many, many years and she is a supporter of Trump. And somehow, we never bring it up," O'Donnell said on a recent episode of The Tangle with Kyle Ridley. O'Donnell added that she does not "really have any people in my life who support Trump - I think it would be very difficult to do that." She expressed a degree of understanding for Judd, citing Judd's personal struggles, including the suicide of her mother.

While Judd has not publicly declared her political affiliation, she visited the White House in 2019 during Trump's presidency to discuss criminal justice reform. In 2017, Judd distanced herself from public criticisms of Trump made by her sister, Ashley Judd, posting on social media, "I am not my sister’s keeper. The end."

O'Donnell's public feud with Trump dates back to 2006 when she co-hosted The View. At the time, O'Donnell criticized Trump for threatening to revoke Miss USA Tara Conner's crown following controversies. O'Donnell called Trump a hypocrite given his personal marital history and questioned his role as a moral figure. Trump responded by calling O'Donnell "a loser" and "out of control."

O'Donnell, who has since moved to Ireland, described the stress level in the United States as high compared to Ireland, where she feels she has found peace. She characterized Trump as having "cruelty," "criminal behavior," "misogyny," "racism," and "homophobia," stating he is "a very dark spirit."