If you’re wondering what Jeff Flake is thinking, rest assured, you’re not alone. But the speculation that hovers over the Arizona senator predates the eleventh-hour move he made that upended, if only temporarily, the contentious confirmation of Judge Brett Kavanaugh. To understand what the 55-year-old is thinking, you need to look at what he has done in the past, what he did Friday — and what he’s doing next.

Flake, who will retire after his first term in the Senate ends in January, will spend Monday afternoon talking about the future of the Republican Party at the New Hampshire Institute of Politics on the campus of St. Anselm College. This will be his second trip this year to the first-in-the-nation-presidential-primary state.

It’s always buzz-worthy when a well-known lawmaker visits the Granite State, especially on the verge of the 2020 presidential primary season. But the timing of Flake’s trip is especially eyebrow raising. Beltway chatter about the senator’s presidential prospects are at an all-time high thanks to his unexpected decision to help vote Kavanaugh out of the Judiciary Committee — but then refuse to back him on the Senate floor until the FBI conducts a brief investigation into the sexual assault allegations brought by Christine Blasey Ford from back in their high school days.

Flake says he regularly contemplates leaving the Republican party, but he isn’t ready to.

While Flake continues to instigate speculation as one of the #NeverTrump Republicans who could be potential challengers to the sitting president, what the senator says and what he does are more at odds than ever. In fact, though he’s set to ruminate on the future of the Republican Party this week, he told Medium on Sept. 18 that he regularly contemplates jumping ship.

“You think about it all the time, but this has been my party my whole life,” Flake says on the sidewalk outside the Senate Russell Office Building the week before the hearings heard round the world. “It’s still, I think, the party that most closely approximates, or can get back to at least, conservative principles, so I’m not ready to abandon it yet.”

Flake won’t reveal his personal red line, which could be because he doesn’t know it himself. Though he effectively pumped the brakes on Kavanaugh, he has also said he will almost certainly vote to confirm him. Last year, he supported all of Trump’s most controversial Cabinet nominees, including Education Secretary Betsy DeVos. And, although earlier this year he threatened to hold up the president’s lower court nominations over the ongoing trade war, he has ended up voting to support the far right swing of the nation’s judiciary.

Flake and Trump are ideologically — though not temperamentally — well-matched. Flake may cringe at the president’s style and tone, but when it comes to policy there’s barely any daylight between them, with the exception of certain immigration and trade issues. The senator has voted in favor of legislation backed or proposed by the White House close to 84 percent of the time, according to the independent, data journalism website FiveThirtyEight.

After initial opposition and then indecision, he announced he would support the Republican tax overhaul bill passed last December. And, perhaps most memorably, he backed a GOP measure in July 2017 that would have permanently gutted the heart of former President Barack Obama’s signature legislative achievement, the Affordable Care Act. The repeal effort memorably failed after a vote from his mentor, the late Sen. John McCain.

Flake first criticized Trump-the-candidate in 2015 for disparaging the reputation of his mentor John McCain.

And after throwing in the towel last fall when he didn’t see a viable path to winning his GOP primary in Arizona, becoming a punch line for the triumphant president who danced on his grave to raucous cheers at rallies, Flake is at a crossroads.

When he officially exits the Senate in January, he has a decision to make: Take on Trump in a GOP presidential primary, drop the Republican mantle altogether and launch a third-party bid, or sit out the contest altogether — possibly setting his sights on becoming yet another cable news talking head.

His decision on the Kavanaugh vote — and his indecision, more broadly — could be the decisive factor.


Flake, like most Republicans in Congress at the time, first criticized Trump-the-candidate in 2015 for disparaging the reputation of McCain (“I like people who weren’t captured,” Trump said of the decorated veteran. But while nearly every Republican lawmaker fell in line by the time Trump took the oath of office, Flake took up the sword of virtue — at least he seems to think he did.

Flake’s plan seems to have been as follows: He would take the high road against a president prone to the low road, and in rising above the social media name calling and made-for-reality-TV antics, he would stand tall and proud in respectful opposition, like his mentor, McCain the Maverick. He thought he’d lead a small but devoted cohort of establishment Republicans intent on safeguarding “conservative values.”

“If someone became the embodiment of an alternative to Trump he would have a real chance, I think, to broaden his appeal from what it happens to be right now,” says long-standing Republican pundit Bill Kristol.

Flake and Trump are ideologically — though not temperamentally — well-matched.

Kristol, along with former New Hampshire GOP Chairwoman Jennifer Horn, former Republican representative David Jolly, and others, are working behind the scenes to try to draft him — and possibly other Trump critics like Nebraska’s Ben Sasse and Ohio’s John Kasich — to explore a primary bid.

Horn tells Medium she’s been impressed by Flake’s actions over the past couple of days.

“For all of us who have daughters, I think, we really appreciated that he was influenced by those voices — that he did listen,” says Horn, a prominent anti-Trump conservative​.

That morning, Flake had announced he’d be sticking with the president’s pick. But he misjudged the moment.

“He’s now created a brand of independence by word but not by deed,” Jolly told Medium shortly after he learned of Flake’s decision. “He’s great at making the comment that you’re like, ‘Yeah, he gets it,’ but then there’s really nothing there. And I think that, whether fair or not, he’s really created this identity where he’s willing to be independent by word but not by deed.”

Roughly four hours later, Flake turned heads again by effectively throwing a last-minute Hail Mary pass. The deal? Flake would vote Kavanaugh out of committee on the condition that he would withhold his “yes” vote on the Senate floor unless the FBI was allowed to investigate the allegations over the next week.

Chaos erupted inside the Capitol. But those conservatives like Horn and Jolly, who were watching from afar, say they were pleased with the decision.

Horn said she has grown concerned about what ramifications the chaotic confirmation fight might have on Republican and Independent voters, particularly women like her, at the polls.

“I’m a conservative Republican who wants to see a conservative on the court,” she says. “But the process that has unfolded over the last two months have put us in a position where we are either going to lose the support of Independents and women, or we are going to lose the support of our base.”

Kristol argues there’s a window, if an admittedly narrow one, for a Republican like Flake to take on Trump. Private polls and focus groups they’ve conducted, he contends, show that Republicans are clinging to Trump now because he’s the party’s standard bearer who is under assault from the left, but he says many voters privately report being open to a solid GOP alternative going forward.

“If someone became the embodiment of an alternative to Trump he would have a real chance.”

He maintains some big donors are eagerly waiting and watching to see who jumps in, including keeping an eye on Flake, who isn’t quite a household name (though that could change after his wildly covered pivot on Kavanaugh).

Other #NeverTrump Republican operatives, meanwhile, have started to discuss getting behind an Independent in the next presidential contest. As Flake told Medium, he’s thought about it but can’t quite get there.

For Flake, who has taken to the Senate floor five well-publicized times this congressional session to lambast Trump, it’s difficult to conceive leaving the party over strongly held differences about civility and tone.

“It is a testament to the condition of our democracy that our own president uses words infamously spoken by Josef Stalin to describe his enemies,” a dry-mouthed Flake warned back in January.

Flake’s calmly delivered diatribes — and possible motives — aren’t lost on the White House either.

“On many occasions, I think that Sen. Flake took the initiating against the administration and sought to provoke reaction,” says Marc Short, Trump’s former White House Director of Legislative Affairs.

From the perspective of the president’s allies, like Short, Flake merely opposes the president’s style — that same flamboyant flair that’s made Trump a household name since the ’80s and that was ultimately enshrined in the American public’s mind with his 14-season stint hosting The Apprentice.

Even there, the two have have more in common than either probably wants to admit. For all his disdain for the president’s low-brow rhetoric, they share a past in reality TV.

Flake, an avid outdoorsman, pitched and appeared, sometimes shirtless, alongside Sen. Martin Heinrich, his Democratic friend from New Mexico, in an hour-long special called Rival Survival on the Discovery Channel in 2014.


When Trump’s angry, we know it, whether by the volume of his Tweets or the way he engages with his ecstatic audience at campaign rallies. When Flake’s fiery mad, he uses big words and makes soaring references to history. That is to say, even his condemnation comes across as mild — the oratorical high road.

Still, his Senate colleagues have taken note and some accuse him of committing the same political sins as Trump.

“I think it’s divisive,” Sen. Richard Shelby, R-Ala., tells Medium, referring to Flake’s admonishments of the president.

By stepping out of his lane, many in the GOP’s old guard now view the Arizona senator with skepticism, questioning whether he’s putting himself above their entire party, not just the president.

What the senator says and what he does are more at odds than ever.

“His numbers were not good in Arizona. I think people noticed that there’s a kind of motive for what he’s doing,” says Oklahoma Senator Jim Inhofe in the fluorescent-lit basement of the Capitol.

Nearly every senator wants the ear of a president, and barring that, the ability to influence the executive agenda — and that has lead most senators, like Inhofe — and, in particular Lindsey Graham, to focus on flattery over frustration.

“Jeff is sincere. He’s offended by the tactics and the style of President Trump,” the South Carolina Republican tells Medium, as he briskly walks along the underground tram cars, originally built to rush elderly or infirmed, or both, to votes. But, Graham, says, “I want to have some influence with him.”

It’s a different story for Flake, who is clawing to be heard. A copy of his 2017 call- to-action, Conscience of a Conservative: A Rejection of Destructive Politics and a Return to Principle, was given to every Republican senator. Twenty of those colleagues were asked directly — and staff for all 50 were queried — whether they’d read it, and not a single one had.

“I haven’t had time for it,” says Arkansas senator Tom Cotton, one of the president’s most ardent supporters, with a smirk.

Along with Cotton, a growing number of critics in Trump’s orbit doubt whether Flake’s motives are pure. One thing the GOP political class agrees on, at least for now, is that any base of support Flake once thought he had has now evaporated.

“There is no constituency among the Republican electorate for Jeff Flake right now, and, you know, he deserves that. He misplayed it, clearly,” says the Republican consultant Matt Mackowiak. “He made himself pretty toxic, both in his home state and nationally among conservative organizations and leaders and most Republicans.”

Finding a donor base depends on finding a voting base, and that’s the biggest hurdle facing what’s left of the #NeverTrump movement in the GOP.

While Flake remains mum about the path he’s plotting going forward, he’s refused to rule out a potential run for president in 2020 or beyond. That doesn’t preclude keeping the door open for publishers and executive producers alike.

“I’ll speak out. I’ll speak out using whatever forum I have. You know, I’m a conservative.

I remain a conservative, and I’d like to remain a Republican, and I do think that we’re going to have to change direction,” Flake tells Medium.

“Nothing focuses the mind like a big election loss, and the pendulum does swing,” he adds.

Flake, for one, hopes that’s true.