The Rise of Vivek. The Return of Masters. The College Libertarians Won’t Go Away.

The 2024 election cycle looks like it will feature not one, but two late-30s contrarians who got their start rapping about libertarianism on elite college campuses. The first is Vivek Ramaswamy, the self-funder now enjoying a “breakout moment” in a presidential primary completely dominated by Donald Trump. The other is Blake Masters, who is reportedly planning another run for US Senate in Arizona after losing to Sen. Mark Kelly by five points in 2022. 

Masters’ reasons for running again are not altogether obvious. His hard-right Senate campaign last year, which was bankrolled by his mentor and former boss Peter Thiel, defined how Republicans squandered the 2022 midterms by nominating candidates far out of step with voters. Masters called abortion “genocide,” repeatedly responded to news about gay people by saying “not everything has to be gay,” and published unsettling clips of himself shooting guns in the desert. The campaign deeply disturbed former close friends from his private day school and Stanford, who didn’t recognize the man they saw in the ominous videos. (Masters said he was inspired by the aesthetics of Terrence Malick, a director best known for a film about a sociopathic killing spree.)

This is not to say Masters had no fans. Last year, I reported that Masters had once written an email to his vegetarian coop at Stanford in which he called democracy “that miserably peculiar American diety [sic].” In another, he recommended an article that advocated for “the abdication of democracy” and replacing it with a world in which the masses accepted a “natural order” led by a “voluntarily acknowledged ‘natural’ elite—a nobilitas naturalis.” 

A poster named Pedro Gonzalez responded to those revelations on Twitter by writing, “This actually makes Blake Masters look great.” Less than a year later, it was reported that Gonzalez, who’d become one of Florida Gov. Ron DeSantis’ biggest boosters online, had sent countless racist and antisemitic text messages. (A representative sample: “whites themselves are too cucked to preserve their own civilizations.”) 

Another Masters fan was Nate Hochman, the twentysomething DeSantis staffer who was fired after it came out that he’d secretly made a pro-DeSantis video featuring the sonnenrad symbol used by Nazis and neo-Nazis. Yet another supporter was Curtis Yarvin, the self-identified absolute monarchist blogger who gave the first and only campaign donation of his life to Masters.

Masters’ campaign generated unprecedented enthusiasm among the kinds of highly online men who fantasize about a right-wing dictatorship.

The goal is not guilt by association but to illustrate a basic fact: Masters’ campaign generated unprecedented enthusiasm among the kinds of highly online men who fantasize about a right-wing dictatorship. In Masters, they saw one of their own, much more than now–Sen. J.D. Vance (R-Ohio), whose race Thiel successfully funded. The problem for Masters was that titillating a subset of nerds, as opposed to, for example, the majority of Americans without college degrees, was not a recipe for success in a race against an incumbent senator who’d gone into orbit. 

During a recent conversation on X organized around “Praying for America and Arizona,” the 37-year-old Masters sounded oddly sedated as he spoke to the roughly 600 people who tuned in. He mentioned that his wife was expecting their fourth child in the coming months. His voice conveyed none of the enthusiasm that would justify spending the baby’s first months running a campaign he’ll likely lose.

Why Ramaswamy is in the race, on the other hand, seems obvious enough. He can. At 38, Ramaswamy already has enough money from a pharmaceutical venture to last him many lifetimes. For a millennial who was nicknamed “The Chairman” during his time at the Harvard Political Union, a chance to occupy a presidential debate stage likely carries the value of many private islands. 

During the first Republican debate last week, it was hard to imagine Ramaswamy enjoying anything more than aggravating Gov. Ron DeSantis, whose super-PAC had pushed for DeSantis to “hammer” Ramaswamy, by repeatedly flapping his hand in the governor’s peripheral vision.

I feel bad for DeSantis having to stand next to Vivek…look at his annoying little hand! pic.twitter.com/6d7lNnCgFr

— Brent Scher (@BrentScher) August 24, 2023

What Ramaswamy believes is more opaque than what Masters believes, but only slightly. The reason for that is Ramaswamy is a better politician and a better liar. “It was a dark day for democracy,” Ramaswamy wrote in a book last year. “The loser of the last election refused to concede the race, claimed the election was stolen, raised hundreds of millions of dollars from loyal supporters, and is considering running for executive office again. I’m referring, of course, to Donald Trump.” Now he corners his opponents for refusing to say they’d pardon Trump on their first day in office. The means justify the end, which is Ramaswamy gaining as much power as possible. 

What Ramaswamy believes is more opaque than what Masters believes, but only slightly. The reason for that is Ramaswamy is a better politician and a better liar.

Like Masters, Ramaswamy has a “mutual friend” in Thiel, a billionaire who concluded long ago that his version of libertarianism was unlikely to be realized through democracy. Ramaswamy, who co-founded an anti-ESG investment firm with Thiel’s backing, is more optimistic about techno-reactionaries’ ability to gain power through the ballot box. The key is to disdain voters by telling them whatever they want to hear regardless of how much it contradicts reality. It might work and, even if it doesn’t, Ramaswamy will have had fun trying. 

For now, it’s easy to mock both candidates. Masters appears on track to lose again. But this Senate race is much different than his first. It is hard to see how we would beat former gubernatorial candidate Kari Lake if she decides to run for Senate. Lake is far better on television—it used to be her job—and is the preferred candidate of the MAGA true believers. But if Masters does make it out of a primary, he could find himself in an unusual three-way primary between Arizona’s now independent Sen. Kyrsten Sinema and her main Democratic challenger, Rep. Ruben Gallego. Strange things could happen.

Similarly, Ramaswamy looks to be one of many presidential candidates who enjoy a moment at the center of the news cycle before eventual defeat. He is frequently compared to Pete Buttigieg, another Harvard grad who asked questions during MSNBC’s Battle for the White House in his youth. But Butigieg is now Transportation Secretary Buttigieg. 

The odds that Ramaswamy would find a spot in a future Trump administration appear high as well. Just this week, Trump praised Ramaswamy as “very intelligent” guy with “a lot of talent,” but warned him not to get too controversial. And while Buttigieg has been criticized from the left for not using the full power of his office, Ramaswamy would be unlikely to face the same criticism from the Peter Thiels of the world.