Why you should care

Because some of these fiery conversations may be taking place again … but on the presidential stage. 

The lineup sounded like a bad bar joke. As Democratic megadonor Tom Steyer called for Donald Trump’s impeachment over his Russia summit in Helsinki, Republican strategist Karl Rove defended Trump by pointing to the president’s sanctions against oligarchs and criticizing Barack Obama. “The previous administration should have taken tough action against a foreign actor meddling in our elections,” Rove said. “I’m sure … that Putin was shaking in his boots,” he added sarcastically.

“Who gives a shit?” interrupted comedian Chelsea Handler, an author and activist. “Republicans constantly are bringing up what Obama didn’t do in comparison to what Trump did. Obama also didn’t kiss Putin’s ass in front of all of the American people.” As Rove added that Obama “stood by while [Russia] took Crimea,” Steyer finally interrupted: “Alright, Karl: Enough, enough.”

How in the world did three people so different get into a room together? Only at OZY Fest, during a heated hourlong panel moderated by OZY CEO and co-founder Carlos Watson that fired among topics like impeachment, gerrymandering, voter suppression and presidential ambitions.

The tensions began early, with Steyer saying that he got involved in national politics in the early 2000s after it became clear (to him) that George W. Bush — whom Rove served as chief strategist — was going to “set the country back 25 years.” After Steyer complained about the Citizens United decision, saying “corporations aren’t people” and that elections should be about “one person, one vote,” Rove got his vengeance — by pointing out that the environmentalist billionaire was one of the biggest Democratic donors in 2016 (spending $90 million, and recently spending $20 million more on ads advocating for Trump’s impeachment).

“Should Steyer be able to spend $40 million and I can only send $100,000?” Rove deadpanned. (Pointedly, Rove, who is tied to the super PAC American Crossroads, added that corporations don’t give money anyway, because “they’re scared to death of offending their customers.”) It’s a question Steyer, who is widely rumored to be preparing a presidential run, will likely face from “1 percent”-decrying Democrats as well in a primary that could include 20 or more candidates in 2020. “He’s running, he’s running,” Rove interrupted when Steyer said he hadn’t made a decision on his candidacy yet, with the conservative Texan getting under the liberal Californian’s skin once again: “He knows so much about me,” Steyer griped, when “he met me 45 minutes ago.”

Sean ozyfest 06619

(From left) GOP strategist Karl Rove spars with comedian Chelsea Handler and activist Tom Steyer, while OZY CEO and co-founder Carlos Watson moderates.

Source Sean Culligan/Ozy

Handler didn’t stay on the sidelines for long, saying Trump’s presidency was a “stain on American history,” colorfully calling it her “fantasy” to see “Donald Trump dragged out of the White House in his boxer shorts and landing in the Rose Garden.” The debate over whether to run to the left or to the center was wasted effort, she said, instead arguing that Democrats should find voters excited about a top concern — from LGBTQ to civil rights to marijuana legalization to abortion rights — and motivate them to head to the polls for that issue. “It’s about getting people activated. I’m not trying to convert Republicans,” said Handler, who has said she was taking 2018 off from showbiz to focus on electing women in the midterm elections.

Despite the fiery start, some areas of consensus formed. Both Rove and Steyer agreed that economic anxiety was a growing problem nationwide. “Let’s give the devil his due. Trump did react to the despondency around the country,” Steyer said, although he believes the president’s proposed solutions are wrong. And while Handler said Democrats should focus on expanding outreach to first-time voters, the other two agreed the parties have to convince swing voters with a positive vision for America. “Elections are won not by energizing and motivating the base but by persuading people who didn’t necessarily share your vision in the past election,” Rove said.

Kirsten Gillibrand talks Supreme Court

The New York senator hasn’t announced her candidacy for president, although she is widely rumored to be preparing a bid. Still, she made her mark on a key issue in the 2018 midterms — voicing sharp opposition to Trump’s Supreme Court nominee Brett Kavanaugh. “He will destroy women’s reproductive freedom,” she said bluntly, urging attendees to tweet at senators to sway their vote.

Gillibrand also answered questions about past views that she would likely face if she enters the Democratic primary for president. A Blue Dog Democrat who supported crackdowns on sanctuary cities when she entered the U.S. House more than a decade ago, she had a change of heart on immigration upon joining the Senate in 2009. “I did not have enough understanding of the issues that impact families all across this country and in New York. I was wrong.” She doubled down on her bid for progressive support, saying Alexandria Ocasio-Cortez’s surprising congressional primary victory this summer was “inspiring.” As OZY noted previously, Gillibrand became the first U.S. senator to adopt an “Abolish ICE” stance after the democratic socialist helped popularize the notion. “She really ran from her heart on issues she cares about,” Gillibrand said of Ocasio-Cortez.

Steyer rolls his sleeves up …

… literally, getting casual backstage in gray jeans and scuffed tennis shoes, before dancing his own rendition of the electric slide. It was followed by some serious talk in an exclusive interview. On the revelations that Trump lawyer Michael Cohen has audio tapes of Trump discussing hush payments to Playboy model Karen McDougal: “There is more evidence right now that this president has met the grounds for impeachment,” Steyer said. While OZY reported last year that Republicans believe such claims would drive conservative voters to the polls, Steyer rejected that notion. “That’s a red herring,” Steyer said. “We polled it and it doesn’t get Republicans to the polls — in fact, it gets Democrats.”

Rove believes the Trumps won’t be a family dynasty

The man knows dynasties, having shepherded Bush through his presidential campaigns. “They certainly sound like they want to, but whether or not they’ll be as successful as the old man is yet to be shown. If you are going to run for mayor or governor of New York, that’s hard enough — might be even harder if your last name is Trump,” Rove said in an interview. “The one who seems to be most energized is Don Jr. Ivanka might have a better shot, particularly if she finds the right spot.”

He also defended Kavanaugh, after reports showed the nominee had suggested a 1974 Supreme Court decision forcing Richard Nixon to turn over the Watergate tapes was wrongly decided. “He has a proper view of what the role of the judiciary is, which is not to become a lawmaking body,” Rove said, arguing that Kavanaugh was merely saying that an independent or special counsel (such as Robert Mueller) needed to be created by Congress.

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