Rosie O’Donnell is back in the headlines, and not just because she might pop in for The View’s 30th anniversary. She’s starring in a one-woman Broadway show, guest-hosting Jimmy Kimmel Live!, talking about daytime television again, and says being back in New York has made her feel “re-famous.”
Rosie O’Donnell sets the record straight: She’s only going back to “The View” as a one-time guest, not a host. pic.twitter.com/VO6plvwKfn
— Vince Langman (@LangmanVince) August 4, 2026
Truth be told, there was a time when I genuinely liked Rosie. I watched The Rosie O’Donnell Show, loved several of her movies, and thought she had a warmth that made her easy to watch. I wasn’t someone who followed every interview or comedy special, but I always enjoyed seeing her on television. That’s what made me start wondering how someone I once found so funny gradually became known almost entirely for one very long feud.
It Didn’t Start With Politics
For a reminder, Rosie and Donald Trump did not start fighting when he ran for president.
Their feud actually began in 2006 over Miss USA winner Tara Conner, who found herself in trouble after reports of underage drinking, partying, and drug use. Trump owned the Miss USA Organization at the time, and nearly everyone expected him to strip her of the crown.
Instead, he announced that Tara would enter rehab, keep her title, and get a second chance.
I found a very old tweet:
Miss USA Tara Conner will not be fired – “I’ve always been a believer in second chances.” says Donald Trump
— Donald J. Trump (@realDonaldTrump) May 12, 2009
Looking back, I have to say I think he made the right call. He could have publicly embarrassed a young woman who was obviously struggling. Instead, he chose accountability, treatment, and redemption.
Rosie saw it very differently.
On The View, she questioned Trump’s character, mocked him personally, and criticized his decision. Trump responded in classic Trump fashion, and what started as a disagreement over one beauty pageant contestant became a feud that has now lasted nearly twenty years.
The Part Everyone Forgot
What surprised me wasn’t how the feud started. It was what happened afterward.
Tara Conner got sober. She rebuilt her life, got married, had a daughter, and now spends much of her time helping people recover from addiction.
That’s a remarkable ending to a story that easily could have gone the other way.
Trump didn’t do the hard work for her. Tara did. But the second chance he offered gave her the opportunity to do exactly that, and she made the most of it.
That’s not a bad legacy for what became one of the biggest celebrity fights of the 2000s.
I hate to say this but the recovering beauty queen sounds a little ungrateful here in this video.
Rosie Found A New Stage
That brings me back to Rosie’s comeback.
One of the things she’s promoting is her one-woman Broadway show, Common Knowledge, where she tells audiences about the last several years of her life, including politics, her move to Ireland, and her ongoing feud with Trump.
If your goal is to tell your personal story, there are podcasts, YouTube channels, documentaries, and social media. Broadway has traditionally been a place where audiences disappear into a story, not where celebrities narrate their own recent headlines.
Then again, maybe this isn’t really about Broadway at all. Maybe it’s about reintroducing Rosie O’Donnell to America. And, of course, money.
I Miss The Old Rosie
Reading these recent headlines sent me down a rabbit hole I wasn’t expecting.
I thought I was writing about Rosie’s return to television. Instead, I found myself revisiting the story that started her feud with Donald Trump and discovering that I had remembered it all wrong.
More than anything, it reminded me how much I enjoyed the Rosie O’Donnell who made people laugh. She had already built a remarkable career before politics became such a large part of her public identity. And now it seems to have consumed her and it’s sad.
She could have taken that noment and done something else entirely and moved on but nope. You can make bad decisions but you don’t have to keep living with them. I almost liken her to Robert Downey Jr with his drug addiction back in the day. I cheered for him when he sobered up and clean up, changing his life around. I hope Rosie can do the same and get some help for her Trump Derangement Syndrome.
Feature Image: AI-generated illustration.
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