WEBVTT

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Welcome back to the Deep Dive. If you're here,

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you know the drill. We give you the shortcut

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to knowledge, not just random facts, but the

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context, the connections, the stuff that makes

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the whole story make sense. Right. And today

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we're diving into, well, quite a story. Four

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decades packed with stand -up comedy, massive

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celebrity, intense conflict, and ending, remarkably,

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with a quest for citizenship abroad. Our subject

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is Rosie O'Donnell, born Roseanne O'Donnell,

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1962. And when you look at her life, it's really

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a study in contrasts, isn't it? Absolutely. You've

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got huge mainstream success. We're talking daytime

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Emmys, major Hollywood films, running headlong

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into these periods of just incredibly intense

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public controversy. Often controversy she seemed

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to actively court, you could say. It really is

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this massive amount of information, this real

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duality. Our mission today for you listening

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is to try and navigate all that. We want to distill

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the core achievements. Yeah, the big moments.

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The major pivots, both personal and political,

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and maybe understand some of that foundational

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stuff, the early life that really shaped her

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public image. It's about clarity, context, you

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know, understanding how someone goes from being

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universally loved as the queen of nice to this

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hyperpolitical figure who just recently actually

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left the United States. OK, so. We've got a pretty

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comprehensive stack here. Covers everything from

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her early stand -up days, the big talk show era,

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the, let's call them, turbulent years on The

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View. Turbulent is one word for it, yeah. And,

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of course, this very recent, very public move

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to Ireland in 2025. And to really understand

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the fire, you kind of have to look at the fuel,

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right? So that means going right back to the

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beginning, her earliest days. Okay, let's unpack

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that foundation. Born, raised, come back to New

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York. Yeah. Roman Catholic family. Irish -American

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roots. Deep Irish -American roots. Her father,

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Edward Joseph O'Donnell, was actually an immigrant

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himself, came over from County Donegal. And that

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detail about County Donegal becomes, well, surprisingly

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relevant much later on, as we'll see. But that

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family life, it wasn't idyllic. Our sources are

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pretty clear. It was marked by significant tragedy

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and also what's described as generational abuse.

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Yeah, the first major blow was her mother, Roseanne

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Teresa. She died from breast cancer. Rosie was

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just about to turn 11. March 1973. Losing your

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mom that young, that's obviously devastating.

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But the sources indicate the trauma ran deeper

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than that loss. They mention a really staggering

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history of family trauma. The phrase used is

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generational abuse and alcoholism. And they explicitly

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state that Rosie and her siblings were sexually

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abused by their father. Yeah. And knowing that,

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I mean, it casts a different light on pretty

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much everything that follows, doesn't it? It

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really does. It provides this. psychological

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engine, maybe, the kind you often see in performers,

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people who need that external validation. Exactly.

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And look at the contrast in her adolescence.

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This private horror happening at home, but publicly.

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She was thriving socially. It's wild. Voted homecoming

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queen, prom queen, senior class president, and

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the key one, class clown. Class clown. That feels

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significant, right? It suggests comedy wasn't

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just fun for her. It was maybe a survival tool.

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It's kind of social armor, yeah. Being the funny

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one, doing imitations like Gilder Radner's Rosanna

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Dana character, apparently it's a way to control

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room, deflect pain, get people to like you. Makes

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perfect sense. Comedy is a defense mechanism.

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And she didn't hang around, dropped out of college

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pretty quick, and hit the stand -up circuit from

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1979 to 84. Started when she was just 17. 17!

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Wow. And then the big break, the thing that really

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took her from clubs to national awareness, that

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came in 84. Star Search. That was the launch

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pad. Right. She wasn't just on it. She killed

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it, right? Totally. Won five weeks in a row.

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That kind of national exposure, you just couldn't

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buy it back then. And that led straight into

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TV roles. Yeah. Early stuff like, give me a break

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in 86. Hosting VH1's stand -up spotlight a couple

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years later. Building momentum. And then the

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leap to movies. And not just small parts. A League

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of Their Own, 1992. That was massive. Huge. And

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look who she's alongside. Tom Hanks, Geena Davis,

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Madonna. Right. And she and Madonna apparently

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hit it off immediately. Became lifelong friends.

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Yeah, that friendship endured. And her film career...

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Through the 90s, it's actually pretty diverse

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when you look back. People kind of forget that

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because the talk show became so huge. True. Like,

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she was the sarcastic best friend in Sleepless

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in Seattle. Perfect casting. Then, totally different,

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Betty Rubble in the live -action Flintstones.

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Huh, yeah. And more serious stuff, too, like

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Beautiful Girls. Yeah. And voice work. Remember

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Turk in Disney's Tarzan? Oh, yeah, the gorilla.

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She had range. But what's maybe even more telling

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than the roles she took are the ones she turned

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down. Especially right before the talk show launched.

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It feels like she was carefully crafting an image.

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Definitely. Two big what -ifs stand out in the

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sources. First, she was apparently seriously

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considered for Elaine Benny's on Seinfeld. Wow.

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Imagine that alternate timeline. Elaine played

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by Rosie O'Donnell. Totally different show. But

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the rejection that really speaks volumes, I think,

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is Hocus Pocus. Ah, yes. Disney wanted her for

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Mary Sanderson, the sort of goofy witch sister.

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Kathy Nott Jimmy eventually got the part. And

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the reason she turned it down, according to our

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sources, she said she explicitly refused to play

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a character who was a frightening evil witch,

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especially one mean to kids. So connect that

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back to the comedy's armor idea. Exactly. It

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fits perfectly. Her whole public persona, her

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coping mechanism maybe, was built on being likable,

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funny, relatable. Not scary, not evil. She was

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building the character that was about to take

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over daytime TV. The Queen of Nice, hashtag tag

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three. The Queen of Nice and the Dawn of Activism,

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1996 -2002. Right. So 1996, the Rosie O'Donnell

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Show launches. Her own production company, Kid

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Row Productions. And it wasn't just a success.

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It was huge. A phenomenon. Yeah. Multiple daytime

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Emmys. It really changed the feel of daytime

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TV for a while. And that nickname stuck. queen

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of nice. It felt like an antidote, didn't it,

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to maybe some of the more cynical talk shows

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or the trashier daytime stuff that was around

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them. Totally. It was all upbeat energy, lighthearted

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interviews. Remember the koosh balls she tossed

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to the audience? Yeah, the koosh balls and the

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constant professed crush on Tom Cruise. Right.

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It made her seem accessible, friendly, celebrity

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culture, but kind of defanged, you know. Less

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edgy. And she really used that New York City

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location to her advantage, became this massive

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champion for Broadway. Oh, absolutely. Constantly

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had casts on, promoting shows, giving away tickets.

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She gave Broadway a huge boost, a real force

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for the arts community there, using her platform

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for generosity. That generosity was central to

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the brand. But then things started to shift.

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That brand started to kind of bummed up against

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her own developing political conscience. The

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big pivot point seems to be 1999, after the Columbine

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High School shootings. That event really seemed

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to galvanize her. And the Queen of Nice persona,

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well, it couldn't really contain the anger she

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felt about that, could it? Not at all. She became

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incredibly outspoken, a leading voice advocating

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for gun control. Got heavily involved with things

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like the Million Mom March. And her statements

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weren't wishy -washy. For a daytime host, they

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were really aggressive. Shockingly direct for

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that time slot. She said, flat out on her show,

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You are not allowed to own a gun. And if you

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do own a gun, I think you should go to prison.

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Wow. But here's the massive contradiction, the

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thing people jumped on immediately. The Kmart

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connection. Exactly. While she's saying this

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on TV, she's also the multimillion dollar celebrity

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spokesperson for Kmart. Which at that specific

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time was the single largest volume retailer of

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firearms in the entire U .S. I couldn't script

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that irony better. The tension was just right

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there out in the open. And it culminated in that.

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incredibly awkward, now infamous interview in

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1999 with Tom Selleck. Oh, yeah. He was on to

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promote a movie, The Love Letter, I think. Yeah,

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but Selleck was also, you know, known for being

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an NRA member and doing some unpaid ads for them.

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And Rosie didn't just ask him about it. She went

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after him. Hard. It was an interrogation, really.

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Pushing him on the NRA's stance on so -called

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assault weapons, trying to get him to apologize

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for being involved with them. Live on daytime

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TV, Selick looked completely blindsided. So uncomfortable

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to watch. She ended it by saying something like

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the conversation hadn't gone how she'd hoped.

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Yeah, a massive understatement. It showed just

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how difficult it was to use that nice platform

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for what was becoming a pretty nasty political

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fight for her. Did the Kmart deal end soon after?

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It did. Later that same year, 1999, there was

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huge backlash from gun rights groups, obviously.

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The pressure mounted. And the contract ended.

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But the fight had become personal, too. The sources

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mentioned security concerns. Yeah, this really

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underscores the reality of that kind of public

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conflict. In 2000, because of threats against

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her and her family, direct results of her gun

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control stance, her security team actually requested

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that her bodyguard apply for a concealed carry

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permit. So the very thing she was fighting against,

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private citizens carrying guns, became something

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her own team felt was necessary to protect her.

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The irony is profound. It shows the real -world

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cost, the personal risk involved in taking such

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a public, controversial stand. So she's already

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deep in political controversy. Then comes another

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major pivot, just as the show is ending in 2002,

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a deeply personal one. Her public coming out

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as a lesbian. The way she did it was very rosy.

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Strategic makeup. Seems like it. First, she played

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a lesbian mom on an episode of Will &amp; Grace.

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Then, shortly after, during a stand -up gig,

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she just declared, I'm a dyke. But the reason

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she gave, the main motivation, wasn't just about

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personal truth, was it? No, not primarily. She

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framed it as explicitly political. It was a direct

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protest against Florida's laws at the time, which

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banned gay people from adopting children. Right.

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She was already a foster and adoptive mom herself.

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So she was using her coming out, her celebrity,

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to shine a huge spotlight on that specific issue.

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Yeah. Affecting LGBTQ families. Which is powerful.

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But inevitably, perhaps, it also caused some

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friction even within the LGBTQ community. How

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so? Well, some activists pointed to all those

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years of her joking about being infatuated with

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Tom Cruise on the show. They argued it felt deceptive,

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like she'd been playing a role for mainstream

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acceptance. Ah. The authenticity question. How

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did she respond? With a very characteristic,

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blunt comeback. She basically said about Cruz,

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I said I wanted him to mow my lawn and bring

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me a lemonade. I never said I wanted to blow

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him. Okay. Yeah, that sounds like her. Using

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humor to deflect criticism. Pretty much. But

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despite that minor controversy, she was widely

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recognized as a major advocate. The Advocate

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magazine named her Person of the Year in 2002.

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She started writing a column for them. So when

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her talk show ended later that year, the Queen

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of Nice chapter was definitively closed. Absolutely.

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The activist was now front and center, and the

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stage was set for even more fireworks. Hashtag

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Chaktag 5E. The turbulent view and the age of

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hyper -controversy. 2006, 2007, 2014, 2015. Okay,

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buckle up. Because the next chapter, starting

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around 2006, it's not just controversial. It's

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like controversy squared, hyper -controversy.

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Yeah, this is when she joins The View. She takes

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over from Meredith Vieira as moderator in September

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2006. And this move, it wasn't just a job change

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for her. It arguably helped change the whole

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landscape of daytime TV. What do you mean? While

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the network probably knew what they were getting,

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to some extent, Rosie immediately brought this

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huge buzz factor, as the sources call it. The

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show became much more focused on news, on arguments.

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Exactly. And the numbers proved it worked, at

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least initially. Ratings shot up 27 % in her

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first year. Record highs for the show. She basically

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demonstrated that conflict could sell, even in

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that traditionally softer daytime slot. It kind

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of paved the way for the sort of Partson shout

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fest we see everywhere now, maybe. You could

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definitely argue that. She and Joy Behar formed

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this strong liberal pairing, constantly taking

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on the Bush administration, the Iraq War. Which

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inevitably put them on a collision course with

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the show's conservative voice at the time. Elizabeth

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Hasselbeck. Constantly sparring. But Rosie's

00:12:25.340 --> 00:12:28.019
controversies often went way beyond typical political

00:12:28.019 --> 00:12:30.639
debate. She took aim at institutions. Like the

00:12:30.639 --> 00:12:32.500
Catholic Church comments. Yeah, that was back

00:12:32.500 --> 00:12:35.139
in 2003, even before The View, talking about

00:12:35.139 --> 00:12:37.840
the abuse scandals. She said she hoped the church

00:12:37.840 --> 00:12:40.039
got sued so much they'd have to melt down some

00:12:40.039 --> 00:12:42.259
of the gold toilets in the Pope's Vatican to

00:12:42.259 --> 00:12:44.440
pay. Oof. Yeah, that's going to generate heat.

00:12:44.600 --> 00:12:46.919
And she didn't stop there, right? On The View

00:12:46.919 --> 00:12:50.350
itself. Nope. 2007, after a Supreme Court ruling

00:12:50.350 --> 00:12:52.950
on abortion, she jumps into this whole separation

00:12:52.950 --> 00:12:56.450
of church and state thing by asking, rhetorically,

00:12:56.669 --> 00:12:59.850
how many Supreme Court judges are Catholic? Again,

00:13:00.029 --> 00:13:03.210
deliberately provocative, designed to get a reaction.

00:13:03.529 --> 00:13:05.669
Absolutely. These weren't accidental slips of

00:13:05.669 --> 00:13:08.169
the tongue. They felt calculated. But sometimes

00:13:08.169 --> 00:13:12.149
the provocation backfired spectacularly, like

00:13:12.149 --> 00:13:15.470
the racial gaffe in December 2006. Oh, the Ching

00:13:15.470 --> 00:13:18.200
Chong incident. Yeah. Trying to imitate Chinese

00:13:18.200 --> 00:13:20.639
newscasters, she used that phrase repeatedly.

00:13:20.980 --> 00:13:23.559
The backlash was intense, especially from Asian

00:13:23.559 --> 00:13:26.720
-American groups who felt betrayed by someone

00:13:26.720 --> 00:13:29.460
seen as a progressive ally. And her apology didn't

00:13:29.460 --> 00:13:31.500
really help, did it? Not really. It got heavily

00:13:31.500 --> 00:13:33.799
criticized. Time called it a pseudo -apology.

00:13:34.100 --> 00:13:35.940
She claimed she didn't know the phrase was that

00:13:35.940 --> 00:13:37.860
offensive, comparing ignorance levels to the

00:13:37.860 --> 00:13:39.919
N -word. Which is already shaky ground. Right.

00:13:40.279 --> 00:13:42.059
But then she kind of undercut the whole thing

00:13:42.059 --> 00:13:44.799
by adding this weird disclaimer, almost joking,

00:13:44.840 --> 00:13:46.879
that she'd probably do something like that again,

00:13:47.000 --> 00:13:49.340
probably in the next week, not on purpose. Hmm.

00:13:49.519 --> 00:13:52.480
It reads as dismissive, doesn't it? Like she

00:13:52.480 --> 00:13:55.539
couldn't fully own the impact of her words. A

00:13:55.539 --> 00:13:57.720
pattern, maybe. It does seem like a pattern.

00:13:57.820 --> 00:14:01.299
That inability to maybe filter or to fully grapple

00:14:01.299 --> 00:14:03.960
with the consequences of her rhetoric. And that

00:14:03.960 --> 00:14:06.340
tendency then led directly into the defining

00:14:06.340 --> 00:14:09.360
feud of her career. The one that really previewed

00:14:09.360 --> 00:14:11.960
our modern political climate. The war with Donald

00:14:11.960 --> 00:14:14.960
Trump. It kicked off in December 2006. Remember

00:14:14.960 --> 00:14:18.159
the Miss USA scandal with Tara Conner? Trump

00:14:18.159 --> 00:14:20.600
made this big show of reinstating her after some

00:14:20.600 --> 00:14:23.220
controversy. Right. Rosie went after him on The

00:14:23.220 --> 00:14:25.509
View, basically accusing him. of exploiting the

00:14:25.509 --> 00:14:28.029
situation for publicity and questioned his moral

00:14:28.029 --> 00:14:31.250
standing to do so oh yeah pointed to his multiple

00:14:31.250 --> 00:14:34.250
marital affairs and questionable business bankruptcies

00:14:34.250 --> 00:14:37.529
now this is 2006 trump remember reality tv star

00:14:37.529 --> 00:14:40.730
tabloid guy not yet the political figure but

00:14:40.730 --> 00:14:43.840
his reaction was Something else. Instantaneous,

00:14:43.840 --> 00:14:46.299
vicious, a total media assault. He threatened

00:14:46.299 --> 00:14:48.480
to sue her, never actually did. But he hurled

00:14:48.480 --> 00:14:50.639
these incredibly personal insults, called her

00:14:50.639 --> 00:14:53.200
names, attacked her appearance. And made that

00:14:53.200 --> 00:14:55.100
really chilling comment about her partner at

00:14:55.100 --> 00:14:57.740
the time, Kelly Carpenter. Yeah, suggesting he'd

00:14:57.740 --> 00:14:59.340
send one of my friends to pick up her girlfriend

00:14:59.340 --> 00:15:02.159
Kelly and I think it would be easy. Just deeply

00:15:02.159 --> 00:15:05.639
unpleasant, threatening stuff. Way beyond typical

00:15:05.639 --> 00:15:08.659
celebrity spats. And this put Barbara Walters,

00:15:08.799 --> 00:15:12.059
the show's creator and sort of den mother. in

00:15:12.059 --> 00:15:14.200
a really tough spot. Totally caught in the middle.

00:15:14.500 --> 00:15:16.820
Rosie felt Barbara didn't defend her strongly

00:15:16.820 --> 00:15:19.440
enough against Trump's attacks. Sources say there

00:15:19.440 --> 00:15:21.539
was a major blow up between them in a dressing

00:15:21.539 --> 00:15:25.820
room over it. Loyalty betrayal. All that raw

00:15:25.820 --> 00:15:28.480
emotion. So the tension is just ratcheting up.

00:15:28.600 --> 00:15:32.100
And it all boils over in May 2007 during these

00:15:32.100 --> 00:15:34.779
really intense on -air debates about the Iraq

00:15:34.779 --> 00:15:37.519
war. This is where she steps into really controversial

00:15:37.519 --> 00:15:40.399
territory regarding 9 -11 truthiness. Right.

00:15:40.440 --> 00:15:42.100
She started questioning the official account

00:15:42.100 --> 00:15:44.419
of the World Trade Center collapse, saying, I

00:15:44.419 --> 00:15:46.279
do believe that it's the first time in history

00:15:46.279 --> 00:15:48.580
that fire has ever melted steel. Which, you know,

00:15:48.600 --> 00:15:50.659
immediately aligns her with 9 -11 conspiracy

00:15:50.659 --> 00:15:53.240
theories. And she didn't stop there with Iraq.

00:15:53.740 --> 00:15:56.419
No, she challenged the whole narrative, asking

00:15:56.419 --> 00:16:00.240
her co -hosts, 655 ,000 Iraqi civilians dead.

00:16:00.419 --> 00:16:03.100
Who are the terrorists? And that line, who are

00:16:03.100 --> 00:16:06.320
the terrorists, was immediately seized upon by

00:16:06.320 --> 00:16:09.320
conservative media as her equating U .S. soldiers

00:16:09.320 --> 00:16:12.000
with terrorists. Whether she meant it that way

00:16:12.000 --> 00:16:14.679
or not, that's how it landed. And that led straight

00:16:14.679 --> 00:16:17.700
to the final explosive confrontation with Elizabeth

00:16:17.700 --> 00:16:20.659
Hasselbeck. Yeah. The core of that argument was

00:16:20.659 --> 00:16:23.559
Rosie feeling that Elizabeth, who she considered

00:16:23.559 --> 00:16:26.659
a friend, wouldn't defend her against those specific

00:16:26.659 --> 00:16:29.960
conservative attacks. She felt betrayed. But

00:16:29.960 --> 00:16:31.580
the actual breaking point, the thing that made

00:16:31.580 --> 00:16:34.159
her walk away, wasn't just the argument itself.

00:16:34.399 --> 00:16:36.240
No. According to the sources, it was a production

00:16:36.240 --> 00:16:39.179
choice. During that heated exchange, the show

00:16:39.179 --> 00:16:42.139
used a really dramatic split -screen visual.

00:16:42.720 --> 00:16:45.700
Rosie on one side, Elizabeth on the other. Pure

00:16:45.700 --> 00:16:48.580
visual conflict. And Rosie saw that as? As a

00:16:48.580 --> 00:16:51.299
setup. She felt the producers deliberately chose

00:16:51.299 --> 00:16:54.639
that visual to maximize the drama, to egg her

00:16:54.639 --> 00:16:57.299
on, as she put it, rather than facilitating any

00:16:57.299 --> 00:17:00.279
kind of real resolution. She felt used for ratings.

00:17:00.600 --> 00:17:02.860
So she quit. Just like that. Two days later,

00:17:02.940 --> 00:17:05.220
she was gone. Walked away from her contract early.

00:17:05.359 --> 00:17:07.299
But in a way, it proved her point about the ratings,

00:17:07.400 --> 00:17:10.980
didn't it? Ironically, yes. ABC News reported

00:17:10.980 --> 00:17:13.680
that those specific arguments, that period of

00:17:13.680 --> 00:17:16.680
intense conflict, gave The View its best ratings

00:17:16.680 --> 00:17:20.680
ever. Conflict sells. She did eventually return

00:17:20.680 --> 00:17:25.099
years later. Briefly. Fall of 2014. New panel

00:17:25.099 --> 00:17:27.740
with Whoopi Goldberg, Rosie Perez, Nicole Wallace.

00:17:27.859 --> 00:17:29.599
But it didn't last long that time either. No,

00:17:29.640 --> 00:17:31.920
only about five months. She left again in February

00:17:31.920 --> 00:17:35.660
2015. Cited health reasons, personal issues,

00:17:35.980 --> 00:17:38.500
maybe the fire wasn't there, or maybe that format

00:17:38.500 --> 00:17:40.619
just wasn't right for her anymore. So, okay,

00:17:40.680 --> 00:17:42.740
conflict seems to be the theme, both on screen

00:17:42.740 --> 00:17:45.140
and off. When she stepped away from hosting,

00:17:45.339 --> 00:17:48.220
she poured that same intensity into other ventures,

00:17:48.279 --> 00:17:50.990
right? business, philanthropy. Yeah, and with

00:17:50.990 --> 00:17:53.289
pretty mixed results. You see this pattern of

00:17:53.289 --> 00:17:55.869
really ambitious projects, some marked by spectacular

00:17:55.869 --> 00:17:58.829
failures and legal fights, and others by incredible

00:17:58.829 --> 00:18:01.490
dedication and success, usually tied to her personal

00:18:01.490 --> 00:18:03.789
passions. The Rosie Magazine venture is a prime

00:18:03.789 --> 00:18:05.589
example of the former, isn't it? Yeah. Launched

00:18:05.589 --> 00:18:07.390
in 2000. Right. Partnered with the publishers

00:18:07.390 --> 00:18:09.910
of McCall's. The idea was to directly compete

00:18:09.910 --> 00:18:12.329
with Oprah's O Magazine, which was massive. And

00:18:12.329 --> 00:18:15.089
it started well. Strong launch, yeah. Circulation

00:18:15.089 --> 00:18:17.950
hit like 3 .5 million, but the partnerships just

00:18:17.950 --> 00:18:23.670
imploded fast. Over what? Control. Specifically,

00:18:23.910 --> 00:18:27.170
editorial control. Rosie wanted final say. The

00:18:27.170 --> 00:18:29.730
publishers resisted. Classic power struggle.

00:18:30.109 --> 00:18:33.069
She quit in 2002, only two years in. And then

00:18:33.069 --> 00:18:35.250
came the lawsuits. Oh, yeah. Both sides sued

00:18:35.250 --> 00:18:37.150
each other for breach of contract. It went to

00:18:37.150 --> 00:18:40.690
trial in 2003. Very public, very messy. And that

00:18:40.690 --> 00:18:43.519
trial produced another one of those just... Jaw

00:18:43.519 --> 00:18:45.759
-dropping rosy moment. The cancer comment, yeah.

00:18:46.220 --> 00:18:48.559
Under cross -examination, talking to a former

00:18:48.559 --> 00:18:50.200
colleague who happened to be a breast cancer

00:18:50.200 --> 00:18:54.099
survivor. She said... What was it exactly? She

00:18:54.099 --> 00:18:56.079
told her essentially that people who lie get

00:18:56.079 --> 00:18:58.619
sick and they get cancer. Oh my God. Linking

00:18:58.619 --> 00:19:01.400
lying to cancer to a survivor's face in open

00:19:01.400 --> 00:19:03.880
court. Just an unbelievable lapse. She apologized

00:19:03.880 --> 00:19:05.759
the next day, said it came from her own trauma

00:19:05.759 --> 00:19:07.779
around her mother's death from cancer, but...

00:19:08.250 --> 00:19:10.450
The damage was immense. How did the lawsuit end?

00:19:10.650 --> 00:19:12.529
The judge eventually threw the whole thing out,

00:19:12.609 --> 00:19:14.509
dismissed both cases, said neither side deserved

00:19:14.509 --> 00:19:16.710
damages, basically called the whole venture a

00:19:16.710 --> 00:19:19.069
wash, a failure on both sides. Okay, so that

00:19:19.069 --> 00:19:21.309
was one big swing and a miss. What about Taboo,

00:19:21.349 --> 00:19:24.589
the musical? Another passion project. She brought

00:19:24.589 --> 00:19:27.549
that Boy George musical to Broadway in 2003,

00:19:27.829 --> 00:19:30.710
championed it heavily, put her own money in.

00:19:30.990 --> 00:19:32.910
But it didn't fare well commercially either.

00:19:33.279 --> 00:19:35.599
No, mostly bad reviews. Closed pretty quickly

00:19:35.599 --> 00:19:38.680
in 2004 after only about 100 performances. A

00:19:38.680 --> 00:19:40.779
financial disappointment for her. But here's

00:19:40.779 --> 00:19:42.160
where you see the other side of the pattern,

00:19:42.240 --> 00:19:45.339
maybe. Her reaction to Taboo's failure was different.

00:19:45.559 --> 00:19:48.039
Totally different. Despite losing money and getting

00:19:48.039 --> 00:19:51.019
panned, Rosie called producing Taboo the most

00:19:51.019 --> 00:19:53.680
fulfilling experience of her entire career. So

00:19:53.680 --> 00:19:55.720
the fulfillment came from the act of creation,

00:19:56.059 --> 00:19:59.319
the passion, not necessarily the commercial success

00:19:59.319 --> 00:20:01.609
or lack of conflict. Seems like it. When her

00:20:01.609 --> 00:20:03.250
ventures failed, it was often about business

00:20:03.250 --> 00:20:05.970
disputes or market realities. When they succeeded

00:20:05.970 --> 00:20:08.109
or when she felt fulfilled, it was because they

00:20:08.109 --> 00:20:10.390
aligned with her core values and activism. Which

00:20:10.390 --> 00:20:12.869
leads us perfectly to Our Family Vacation. Exactly.

00:20:13.150 --> 00:20:16.130
Co -founded in 2003, and the mission was crystal

00:20:16.130 --> 00:20:18.940
clear. Deeply personal for her. Providing the

00:20:18.940 --> 00:20:21.980
very first all gay and lesbian family vacation

00:20:21.980 --> 00:20:24.859
packages. Revolutionary at the time. The first

00:20:24.859 --> 00:20:28.480
cruise they did in 2004 had 1 ,600 passengers,

00:20:28.720 --> 00:20:32.740
including 600 kids. It was about creating a safe,

00:20:32.779 --> 00:20:35.400
affirming space. More than just a vacation, right?

00:20:35.440 --> 00:20:37.460
They tackled issues. Yeah. Held discussions about

00:20:37.460 --> 00:20:39.859
adoption, surrogacy, things that were still really

00:20:39.859 --> 00:20:42.420
challenging for LGBTQ families to navigate openly

00:20:42.420 --> 00:20:44.859
back then. She wasn't just talking about support.

00:20:44.980 --> 00:20:47.410
She was building the infrastructure. for it using

00:20:47.410 --> 00:20:50.529
her resources and her philanthropy goes way beyond

00:20:50.529 --> 00:20:53.710
that one venture the scale is huge immense remember

00:20:53.710 --> 00:20:57.069
her memoir find me from 2002 she took the entire

00:20:57.069 --> 00:20:59.430
three million dollar advance from that book three

00:20:59.430 --> 00:21:01.230
million dollars and used it to start her for

00:21:01.230 --> 00:21:03.509
all kids foundation which according to sources

00:21:03.509 --> 00:21:06.009
has given out over 22 million dollars in grants

00:21:06.009 --> 00:21:09.410
since then Wow and she had some creative fundraising

00:21:09.410 --> 00:21:12.440
methods too huh Yeah, the Listerine story is

00:21:12.440 --> 00:21:15.220
classic Rosie. Apparently, Scope, a Listerine

00:21:15.220 --> 00:21:18.119
competitor, ran some ad calling her unkissable

00:21:18.119 --> 00:21:20.299
or something like that. Okay. So instead of just

00:21:20.299 --> 00:21:22.200
getting mad, she partnered with Listerine. They

00:21:22.200 --> 00:21:25.380
agreed to donate $1 ,000 to her foundation every

00:21:25.380 --> 00:21:28.000
single time a guest kissed her on the Rosie O'Donnell

00:21:28.000 --> 00:21:31.059
show. No way. That's brilliant. Turning an insult

00:21:31.059 --> 00:21:33.940
into cash for charity. Totally. Raise over $350

00:21:33.940 --> 00:21:37.099
,000 just from that one stunt. And overall, the

00:21:37.099 --> 00:21:39.769
giving is substantial. Sources report she's donated

00:21:39.769 --> 00:21:42.910
well over $100 million in total throughout her

00:21:42.910 --> 00:21:45.170
career. Including putting a massive chunk of

00:21:45.170 --> 00:21:47.650
money from one contract straight into a trust.

00:21:47.869 --> 00:21:50.089
Yeah, $50 million from a five -year contract,

00:21:50.369 --> 00:21:53.250
put it into an irrevocable trust just for charitable

00:21:53.250 --> 00:21:55.650
giving. Whatever else you say about her, her

00:21:55.650 --> 00:21:58.190
financial commitment to her causes is undeniable.

00:21:58.450 --> 00:22:00.730
Shifting gears a bit, let's talk about her health.

00:22:01.089 --> 00:22:03.630
Because the sources draw a direct line from that

00:22:03.630 --> 00:22:06.369
early trauma we discussed to her ongoing struggles,

00:22:06.569 --> 00:22:08.980
both mental and physical. It's a through line,

00:22:09.079 --> 00:22:11.400
yeah. She's been open about dealing with major

00:22:11.400 --> 00:22:14.480
depressive disorder, PTSD, severe anxiety. And

00:22:14.480 --> 00:22:17.200
she explicitly connects it back. Yes. She's publicly

00:22:17.200 --> 00:22:19.539
attributed her mental health issues and also

00:22:19.539 --> 00:22:22.339
body image struggles directly to the sexual abuse

00:22:22.339 --> 00:22:24.519
she suffered from her father as a child. That

00:22:24.519 --> 00:22:27.130
armor of comedy, like we said. It covered the

00:22:27.130 --> 00:22:29.210
wounds but didn't heal them. Seems that way.

00:22:29.329 --> 00:22:31.390
And physically, she's had some serious scares,

00:22:31.509 --> 00:22:33.930
too. There was a bad staph infection back in

00:22:33.930 --> 00:22:36.829
2000. Almost lost her hand, apparently. But the

00:22:36.829 --> 00:22:39.470
big one was the heart attack in 2012. Yeah, August

00:22:39.470 --> 00:22:42.829
2012. Found out she had a major artery, the widow

00:22:42.829 --> 00:22:46.390
maker, 99 % blocked. needed a stent immediately.

00:22:46.710 --> 00:22:48.769
That sounds like a massive wake -up call. Absolutely.

00:22:49.150 --> 00:22:51.769
It prompted a complete lifestyle overhaul. She

00:22:51.769 --> 00:22:53.849
became a big advocate for preventative heart

00:22:53.849 --> 00:22:57.009
health, adopted a strict whole foods, plant -based

00:22:57.009 --> 00:22:59.410
diet following Dr. Esselstyn's work. She stuck

00:22:59.410 --> 00:23:01.750
with that. Seems so, though she also manages

00:23:01.750 --> 00:23:04.630
type 2 diabetes. But that heart attack was a

00:23:04.630 --> 00:23:06.750
clear turning point in focusing on her physical

00:23:06.750 --> 00:23:09.509
health. And we also see her mental health intersecting

00:23:09.509 --> 00:23:11.609
with the political climate later on. The sources

00:23:11.609 --> 00:23:13.769
mentioned struggles with alcohol. Yeah, she'd

00:23:13.769 --> 00:23:16.049
given up drinking back in 2008, partly for weight

00:23:16.049 --> 00:23:19.109
loss. But she revealed that after the 2016 election

00:23:19.109 --> 00:23:21.730
with Trump winning. The old adversary. Right.

00:23:21.869 --> 00:23:24.390
She said she became very depressed and started

00:23:24.390 --> 00:23:26.490
over drinking again as a way to cope with that

00:23:26.490 --> 00:23:30.410
political reality. A stark reminder of how intertwined

00:23:30.410 --> 00:23:32.650
her personal well -being in the political world.

00:23:37.970 --> 00:23:40.049
That intertwining of the personal and political

00:23:40.049 --> 00:23:42.329
is really evident in her family life, too, isn't

00:23:42.329 --> 00:23:45.890
it? Her relationships, her kids, it's all bound

00:23:45.890 --> 00:23:48.470
up with her activism. Absolutely. She adopted

00:23:48.470 --> 00:23:52.450
her first son, Parker, way back in 1995, even

00:23:52.450 --> 00:23:54.970
before the talk show really took off. He later

00:23:54.970 --> 00:23:57.710
went to Valley Forge Military Academy, interestingly

00:23:57.710 --> 00:24:00.650
enough. And her first marriage. to Kelly Carpenter

00:24:00.650 --> 00:24:03.650
in 2004, that wasn't just a private ceremony.

00:24:03.910 --> 00:24:05.650
No, it was a deliberate political statement.

00:24:05.710 --> 00:24:07.490
They got married in San Francisco during that

00:24:07.490 --> 00:24:09.910
brief period when Mayor Gavin Newsom was issuing

00:24:09.910 --> 00:24:12.849
licenses to same -sex couples. Specifically as

00:24:12.849 --> 00:24:16.109
a challenge to George W. Bush. Explicitly, defiance

00:24:16.109 --> 00:24:18.329
against his push for a constitutional amendment

00:24:18.329 --> 00:24:21.349
banning gay marriage, using her wedding as activism.

00:24:21.769 --> 00:24:23.710
But that marriage didn't legally stand for long,

00:24:23.829 --> 00:24:26.509
did it? No, the California Supreme Court nullified

00:24:26.509 --> 00:24:29.349
those marriages later that same year. Rosie and

00:24:29.349 --> 00:24:32.069
Kelly separated in 2007. Her second marriage

00:24:32.069 --> 00:24:34.529
was to Michelle Rounds. Yes, married in 2012.

00:24:34.650 --> 00:24:37.250
They adopted a daughter, Dakota, together, but

00:24:37.250 --> 00:24:40.230
they divorced in 2015. And then, very sadly,

00:24:40.369 --> 00:24:43.549
Michelle Rounds died by suicide in 2017. Just

00:24:43.549 --> 00:24:46.089
layers of difficulty and tragedy there. Which

00:24:46.089 --> 00:24:48.109
brings us to maybe the most difficult recent

00:24:48.109 --> 00:24:50.089
development involving her daughter, Chelsea.

00:24:50.349 --> 00:24:53.049
Yeah, this is tough stuff. And it really seems

00:24:53.049 --> 00:24:55.900
to highlight the... ongoing impact of that generational

00:24:55.900 --> 00:24:57.940
trauma we talked about earlier. People might

00:24:57.940 --> 00:25:00.059
remember Chelsea went missing for a time back

00:25:00.059 --> 00:25:03.039
in 2015 that made headlines. But the situation

00:25:03.039 --> 00:25:06.230
described in late 2024 sources is. Much more

00:25:06.230 --> 00:25:08.769
serious. Extremely serious. Arrests in Marinette

00:25:08.769 --> 00:25:11.490
County, Wisconsin. The charges listed are harrowing.

00:25:11.529 --> 00:25:14.210
Child neglect, domestic abuse, maintaining a

00:25:14.210 --> 00:25:17.309
drug trafficking facility, meth possession, illegally

00:25:17.309 --> 00:25:20.470
getting prescriptions, THC possession. And the

00:25:20.470 --> 00:25:22.349
reported details about the conditions where her

00:25:22.349 --> 00:25:25.490
own child, Rosie's grandchild, was found. Just

00:25:25.490 --> 00:25:29.349
awful. The sources mention crack pipes, feces,

00:25:29.369 --> 00:25:31.509
and garbage in the house where the 11 -month

00:25:31.509 --> 00:25:34.150
-old was living. It's a devastating picture.

00:25:34.529 --> 00:25:38.589
Suggests that cycle of trauma, addiction, instability.

00:25:39.309 --> 00:25:42.569
It's continuing despite Rosie's fame and resources.

00:25:42.990 --> 00:25:45.309
A deeply private struggle playing out in the

00:25:45.309 --> 00:25:47.930
most public way imaginable. And it's against

00:25:47.930 --> 00:25:51.150
this backdrop of personal crisis that Rosie makes

00:25:51.150 --> 00:25:53.049
her biggest political statement yet. The move

00:25:53.049 --> 00:25:56.609
to Ireland. Expatriation. Right. March 2025.

00:25:56.910 --> 00:25:59.430
Yeah. Just a couple of months after Donald Trump's

00:25:59.430 --> 00:26:02.089
second inauguration. She announces she had actually

00:26:02.089 --> 00:26:04.250
moved to Ireland two months prior with her younger

00:26:04.250 --> 00:26:06.410
child, Clay. And her reasoning was explicitly

00:26:06.410 --> 00:26:09.490
political. She cited heartbreak despair over

00:26:09.490 --> 00:26:11.390
the U .S. political direction, said they felt

00:26:11.390 --> 00:26:13.089
they needed to take care of ourselves and make

00:26:13.089 --> 00:26:16.289
some hard decisions. A complete physical disengagement

00:26:16.289 --> 00:26:18.089
for the American political scene she'd been so

00:26:18.089 --> 00:26:20.730
central to for decades. And she's making it official,

00:26:20.829 --> 00:26:23.109
right? Applying for citizenship. Yes, through

00:26:23.109 --> 00:26:25.869
dissent. Leveraging her father's roots, remember

00:26:25.869 --> 00:26:27.990
Edward Joseph O'Donnell from County Donegal.

00:26:28.069 --> 00:26:30.490
Ah, there it is. Full circle. Using that heritage

00:26:30.490 --> 00:26:32.890
to find a new home. Initially rented near Dublin

00:26:32.890 --> 00:26:36.609
in Halth, but then moved. Yeah, sources say she

00:26:36.609 --> 00:26:38.930
moved to Sandymount, another Dublin coastal suburb.

00:26:38.990 --> 00:26:41.869
The reason given was very practical, very personal.

00:26:42.450 --> 00:26:44.789
Finding a special school for her daughter, Dakota,

00:26:45.130 --> 00:26:48.349
who is autistic. So seeking refuge, seeking support

00:26:48.349 --> 00:26:51.009
for her family. But even across the Atlantic,

00:26:51.230 --> 00:26:53.769
the conflict found her. Of course it did. In

00:26:53.769 --> 00:26:56.849
July 2025, who weighs in but former President

00:26:56.849 --> 00:26:59.910
Trump? Naturally. Publicly threatening to try

00:26:59.910 --> 00:27:02.450
and revoke her U .S. birthright citizenship because

00:27:02.450 --> 00:27:04.430
she left and criticized him. It's almost surreal.

00:27:04.809 --> 00:27:07.849
Even in self -imposed exile, that defining feud,

00:27:07.970 --> 00:27:10.950
that conflict she was so much a part of, continues

00:27:10.950 --> 00:27:14.670
to shape her story. Hashtag tag tag seven, conclusion

00:27:14.670 --> 00:27:17.410
and provocative thought. So when you pull back

00:27:17.410 --> 00:27:19.670
and look at the whole arc. these four decades.

00:27:19.930 --> 00:27:22.710
It really is a story of extremes, isn't it? Molded

00:27:22.710 --> 00:27:26.150
by that intense early trauma, the loss, the abuse.

00:27:26.369 --> 00:27:28.369
Which maybe necessitated the creation of that

00:27:28.369 --> 00:27:30.950
first public persona, the queen of nice, that

00:27:30.950 --> 00:27:33.029
friendly, funny armor. Yeah, but that armor got

00:27:33.029 --> 00:27:35.109
shed pretty quickly, didn't it? Swapped for the

00:27:35.109 --> 00:27:37.910
heavy artillery of the political activist, the

00:27:37.910 --> 00:27:40.789
commentator. And she wielded that platform with

00:27:40.789 --> 00:27:43.849
real conviction on issues she cared about. LGBTQ

00:27:43.849 --> 00:27:48.089
adoption rights, gun control. pouring huge amounts

00:27:48.089 --> 00:27:51.230
of her own money, over $100 million, into backing

00:27:51.230 --> 00:27:54.049
those causes. Her successes often came from that

00:27:54.049 --> 00:27:56.970
place of care. Definitely. Yet, at the same time,

00:27:57.009 --> 00:28:00.049
she engaged in rhetoric that was undeniably inflammatory,

00:28:00.349 --> 00:28:02.630
often seemed ill -considered, even reckless.

00:28:02.950 --> 00:28:05.589
The comments about the Catholic Church, the cancer

00:28:05.589 --> 00:28:08.430
comment during the trial, the 9 -11 steal comments.

00:28:08.490 --> 00:28:10.809
She didn't just participate in conflict TV, she

00:28:10.809 --> 00:28:13.470
arguably helped pioneer it on daytime. Those

00:28:13.470 --> 00:28:15.809
arguments on The View, especially with Hasselbeck,

00:28:15.890 --> 00:28:18.650
became must -see TV precisely because they were

00:28:18.650 --> 00:28:21.390
so explosive. Ratings gold. She understood the

00:28:21.390 --> 00:28:24.150
market for partisan conflict and she leaned into

00:28:24.150 --> 00:28:27.009
it hard. Her later career absolutely thrived

00:28:27.009 --> 00:28:29.369
on the heat, the friction, the debates she ignited.

00:28:29.430 --> 00:28:31.690
She was a central figure in defining that divisive

00:28:31.690 --> 00:28:34.410
tone in American culture. For decades. And now.

00:28:34.890 --> 00:28:37.289
She's physically left, abandoned the arena, moved

00:28:37.289 --> 00:28:39.450
to Ireland, citing political despair, needing

00:28:39.450 --> 00:28:41.670
to protect herself and her family. Fleeing the

00:28:41.670 --> 00:28:43.869
very climate she was instrumental in creating

00:28:43.869 --> 00:28:46.109
and amplifying. Which brings us to our final

00:28:46.109 --> 00:28:48.930
thought. Something for you, the listener, to

00:28:48.930 --> 00:28:50.789
chew on, based on everything we've just laid

00:28:50.789 --> 00:28:53.400
out from the sources. Yeah. Considering how much

00:28:53.400 --> 00:28:55.680
of her later career was built on generating,

00:28:56.000 --> 00:28:59.000
participating in, and frankly, benefiting from

00:28:59.000 --> 00:29:01.599
public political conflict. Does a celebrity who

00:29:01.599 --> 00:29:04.680
spent decades defining and thriving on that kind

00:29:04.680 --> 00:29:07.880
of warfare shaping that very climate? Does she

00:29:07.880 --> 00:29:10.359
then possess the right to simply step away, move

00:29:10.359 --> 00:29:13.359
abroad, seek citizenship elsewhere, citing heartbreak

00:29:13.359 --> 00:29:15.220
over the state of the country she herself helped

00:29:15.220 --> 00:29:17.759
to shape? Is it a valid retreat or an abdication

00:29:17.759 --> 00:29:19.160
of sorts? Something to think about.
