The Swamp

Machiavelli in the White House: Is This the Most Powerful Man in Trump’s Administration?

Can Michael Anton, a Machiavelli enthusiast and amateur sartorialist, wrap Trumpism in a veneer of respectability and sell it to the Republican establishment?
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Michael Anton waits in the East Room of the White House in Washington D.C., February 16, 2017.From A.P./Rex/Shutterstock.

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On September 5, 2016, long before Donald Trump’s shocking election victory—before the Comey letter, before the Billy Bush tape—a lengthy essay was published with minimal fanfare on the Claremont Review of Books’ Web site. Few outside of the solemn world of high conservatism knew of its existence. The majority of political reporters glossed over it. But to the readers of the Review—the right-wing thought leaders, the talk-show hosts, the more erudite Republicans on Capitol Hill—it landed as cacophonously as a jetliner crashing into a Pennsylvania field. The article was written under the nom de plume Publius Decius Mus, but it was notable less for the anonymity of its author than its terrifying thesis. “2016 is the Flight 93 election: charge the cockpit or you die,” it began. Decius continued: “A Hillary Clinton presidency is Russian Roulette with a semi-auto. With Trump, at least you can spin the cylinder and take your chances.”

That opening paragraph descended into an apocalyptic argument for why Trump, a man who gleefully opposed decades of Republican doctrine, needed to be president. In short, only he could prevent the inexorable decline of the American experiment. Decius accused conservatives of being self-motivated, selling their ideals to think tanks, and selling out to the Davos class. Trump was hardly a perfect candidate, Decius conceded, but the alternative was an America run by progressives who appeared, in his estimation, hellbent on eliminating borders, pushing America’s wealth outside, and letting the wrong people in. “The ceaseless importation of Third World foreigners with no tradition of, taste for, or experience in liberty means that the electorate grows more left, more Democratic, less Republican, less republican, and less traditionally American with every cycle,” he wrote. “This is the core reason why the Left, the Democrats, and the bipartisan junta … think they are on the cusp of a permanent victory that will forever obviate the need to pretend to respect democratic and constitutional niceties. Because they are.”

The “Flight 93” essay, as it came to be known, horrified the Review’s staunchly conservative readers. “It was as if PETA had published a barbecue cookbook,” one former Review contributor, who insisted on anonymity, told me. Within hours, several members of the conservative establishment rushed online to condemn Decius’s vision as xenophobic and authoritarian. “It’s the Burning Man of straw men,” wrote Ben Howe at Red State. Rush Limbaugh, on the other hand, loved it, reading entire paragraphs of the essay to his 13 million listeners over the course of several shows. “I’m telling you, folks, it is really good,” he said, enviously. “I was silently jumping for joy because it contains so much of what I said. But it’s said so well here and so pointedly and the gloves off.”

“The Flight 93 Election,” however, was not written by some kook or Limbaugh enthusiast, or even a fringe member of the alt-right. Earlier this month, The Weekly Standard revealed that the author was indeed Michael Anton, a former George W. Bush–era speechwriter, and private-equity executive, with a propensity for fine suits and crisply folded pocket squares, who occasionally moonlighted over the years in conservative scholarship. “I’m a hypocrite. But ‘hypocrisy is the tribute that vice pays to virtue’, right?” Anton told me, acknowledging some of what he called his “blue state” tastes. “I can suppress the fact that I’m awake to these realities, or I can admit it and speak out.”

But Anton, of course, is not merely an aggrieved intellectual who likes fancy clothes. By the time of the Decius reveal, he had a seat on Donald Trump’s National Security Council. And he had assumed a role in the White House similar to Obama’s deputy national security adviser for strategic communications, Ben Rhodes, a former struggling novelist and campaign speechwriter who would become known for bragging about creating a media “echo chamber” to amplify the administration’s international message to the public. (Rhodes’s actual efficacy in articulating and selling such a vision has since become a hotly disputed topic and a cautionary tale in exit-interview protocol.)

In some ways, Anton’s job is even more ambitious. He is charged with not only policy prescriptions, but messaging a palatable form of Trumpism to the wider world—a role that makes him something of an admixture of Steve Bannon, Kellyanne Conway, Stephen Miller, and Sean Spicer rolled into the form of a former establishment Republican. Decius, it seems, has entered the cockpit.

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To understand Anton, one has to understand a bygone California. Anton grew up in the Golden State during the 70s and 80s, when the jobs were plentiful and the public-education system was the best in the country. “Most of what he writes about California, like most of what he writes about America, is a kind of lament for a California that was more friendly to the middle class, and less economically and culturally divided—and probably more Republican, as you might say, in the Reagan days and before,” Charles Kesler, who taught Anton at the Claremont Graduate University and is the editor of the Claremont Review of Books, recently told me. (Disclosure: I studied under Kesler at Claremont McKenna College.)

Anton, himself, agreed with this characterization. “California is a sort of high-low combo with a shrinking middle,” he told me over the phone, his voice full allegro. “The political class and the elites in California are sort of happy about it. ‘Oh, we have Hollywood, we have Silicon Valley, we have all these commanding heights!’ And you say, ‘Yeah, but you don’t really have what it used to have, a thriving middle class.’ Their attitude is just sort of dismissive—‘Who needs that?’—and that trend seemed to be endemic to elites from coast to coast.”

Understanding Anton also requires an understanding of the Claremont Institute, a conservative think tank affiliated with the university, in a Southern California college town surrounded on all sides by the Inland Empire. Anton entered this milieu after graduating from U.C. Berkeley and going to C.G.U., where he became an acolyte of the West Coast Straussians, the conservative academics who spend their sun-drenched days thinking about the Western philosophical pursuit of political excellence, the end result of innate human virtue. Here, in the mid-90s, Anton absorbed the Straussian interpretations of Socrates and Aristotle, pored over the natural law of Saints Augustine and Aquinas, dissected the virtues of America’s Founding Fathers, and studied the nuts and bolts of the federal government in action.

Anton, in particular, specialized in the work of 16th-century Italian philosopher Niccolò Machiavelli, the godfather of modern realpolitik political philosophy, whom he affectionately called “Nick.” Machiavelli, of course, was a profoundly dark cynic and amoral realist, who viewed his high-minded predecessors as foolishly idealistic. Anton stumbled across Machiavelli’s The Prince during his undergraduate years, and later glommed onto Strauss’s Thoughts on Machiavelli, which he says he frequently re-reads to this day. “Strauss famously begins his teachings by saying, ‘I’m going to begin from the point that the old-fashioned and simple opinion is that Machiavelli was a teacher of evil,’ ” said Anton, who eventually published several academic papers on Machiavelli, told me. Indeed, Machiavelli, who broached murdering a entire bloodline of defeated rulers to consolidate power, can be easily construed as dystopian. But Anton sees it another way: yes, he conceded, the philosopher was chilling, but also a rhetorical iconoclast in his own right. “Strauss’s view is that Machiavelli kick-starts modernity,” he told me, walking me through how the Florentine thinker violently broke with the classical philosophers, declared that rulers acting virtuously was for the weak, and sent “the intellectual world on a new trajectory.” One suspects that Anton believes that his philosopher hero stormed the cockpit of ancient Florence.

Machiavelli, naturally, made appearances in Anton’s essays on his beloved home state: ”It’s safe to say that Machiavelli would be appalled by contemporary California—a society perhaps more characteristically modern than any on the planet today,” he wrote in 2014. “He might also look askance at the rampant hedonism unalloyed with any virtue, but in his honesty he would have to admit that his ideas led to it, in almost a straight line.”

To the Claremont Review of Books contributor, Anton’s obsession with “Nick” was the key to understanding “Flight 93.“ “Machiavelli’s central theme is the consolidation of power, including by means that he himself acknowledges as ruthless and wicked, and he takes a very instrumental approach to wickedness and morality,” this person told me. “And that at least gestures toward why someone might conclude that authoritarianism is justified if it will be politically useful to their own side.”

Michael Flynn stands with K. T. McFarland and Michael Anton, center, during a daily news briefing at the White House, in Washington D.C., February 01, 2017.

From A.P./Rex/Shutterstock.

Anton’s intellectualism settled into the background during his early professional years as he took on, according to his LinkedIn profile, various speechwriting gigs for mainstream Republicans—for then New York mayor Rudy Giuliani, for Condoleezza Rice when she was national security adviser, and for Rupert Murdoch. A former colleague of Anton’s relayed to me an anecdote of him referring to himself as the News Corp. chairman’s “house intellectual,” adding that there was a “genuine question of whether he was being self-deprecating.” Anton insisted that, in fact, he wasn’t. “When he hired me, he said ‘Well, you’re going to be the speechwriter, but there’s going to be these ad hoc projects, and new topics that I’m interested in.’ He sort of sold it that way. There wasn’t a whole lot of follow through on that side of it.”

After writing speeches for Giuliani’s failed 2008 campaign, Anton pivoted into the private sector—first as the director of communications at Citigroup, and then as a managing director for BlackRock, a multi-trillion-dollar asset-management firm run by the fervently pro-Hillary Larry Fink. During 2016, he moonlighted on the side by publishing controversial political treatises in the pro-Trump Journal of American Greatness as Decius.

Anton seemed to be a fellow of many alter egos. From time to time, he submitted articles under his own name to various conservative journals and magazines such as The Weekly Standard and The National Review. He also spent a year working in the kitchens of L’Ecole in Manhattan, studying French cuisine and carefully maintaining a set of Japanese knives, he recently told Yahoo, which dubbed him “the most interesting man in the White House.” He even wrote an entire book concerning men’s fashion under the nom de plume Nicholas Antongiavanni, in the voice of his beloved Machiavelli. Suits were a passion of his, he revealed to Forbes in an interview promoting the book, admitting his love of custom tailoring, a fondness for suspenders, and a hatred for Hermès ties (“Their designs are static and have been done to death”) and business casual (“It takes men out of the realm of predictability and that creates problems”). “He has a great sense of humor that’s subtly self-deprecating,” his former colleague told me. “Mostly he’s just kind of uptight, [and] his insistence on sartorial splendor is, I think, a metaphor for a lot.”

After Trump’s election, Anton, whose pen name was an open secret among certain segments of the conservative intelligentsia, was suddenly in demand. He was, after all, a seasoned speechwriter with meaningful experience on the N.S.C., and a true Trump supporter amid a conservative foreign-policy community that was signing their names to letters condemning the new president. Anton says that Peter Thiel, the Trump-supporting tech billionaire, who had attended several Claremont Institute symposiums, introduced him to the Trump transition team. He eventually hired him as the N.S.C.’s senior communications director.

Anton has described his job as little more than speechwriting and managing the press offices for the N.S.C. But he assumes the same position that Ben Rhodes held during the Obama administration, and Anton said that he had Rhodes’s duties, “more or less.“ The job not only comes with a seat on the National Security Council, but, if it continues to resemble Rhodes’s portfolio, it could place Anton in charge of coordinating, distilling, and selling a cohesive message of Trumpism across the State Department and Defense Department and the intelligence community, through every spokesman and ambassador, through every international goodwill program and counter-terrorism publicity campaign, through the Fulbright Scholarships and Voice of America, presenting America’s case to the world.

But whereas Rhodes envisioned himself as an author writing narratives to the public, Anton, an academic at his core, seems prepared to argue and defend a vision of a corrupt, xenophile country whose power structure needs to be torched. It remains to be seen whose method will win out and change the world the most, but one thing is certain: “I’m surprised Ben Rhodes did Ben Rhodes’s job,” Kesler joked. “He had less experience and fewer qualifications, it seems to me, than Anton.”

Few who knew him back in the day as an establishment speechwriter saw Anton’s specific turn to populism coming. A former co-worker from the Bush White House said it was akin to seeing a “perfectly normal” colleague from back in the day suddenly publish an essay trying to convince readers that he was Napoleon Bonaparte. But Kesler, who had watched Anton’s intellectual development over the years, disputed the idea that his former pupil had gone off the Straussian reservation, pointing to an essay (written under his own name) in which he trashed the San Francisco tech elite as “loyal to nothing and no one but themselves and their own messianic ambitions to remake the world into a playground for Übermenschen.”

Anton, self-styled intellectual and amateur sartorialist, fits uneasily into Trump’s base, particularly the fringe elements of the alt-right that have supported his ascendance. He, too, appears sensitive to separate his doctrine from some of the comments one might read on Breitbart. “Could I just ask you bluntly,” he recently asked Yahoo’s Hunter Walker, “are you going to, like, repeat any of this bullshit that I’m a white nationalist and anti-Semite?” Indeed, as conservative CNN commentator Matt Lewis put it to me, Anton was not a true alt-right figure. But, according to Lewis, Anton’s Reagan-era conservatism, combined with his “apocalyptic outlook” on America’s future, overlaps with the alt-right’s xenophobic impulses, thereby establishing an uneasy common ground between them and the mainstream conservative salon-goers of Washington. “I’d say maybe that every alt-righter agrees with the “Flight 93” essay, but not everyone who liked the essay is an alt-righter,” Lewis observed.

But the former colleague of Anton’s rejected the premise outright, arguing that Anton was using his urbanity as cover for his “ethno-nationalist, nativist” urges. “Most folks have beliefs that they cultivate over time,” his former colleague said, referring not just to Anton, but others of his ilk. “But to have that become a high-thread count suit of armor that you wear around the world seems to be something decidedly different.” He then posed a question, one that, perhaps, any of Washington’s smart, cultured Republicans may be asking themselves in these times: “If all that artifice of sophistication is, at the end of the day, revealed to be nothing more than an echo of Breitbart, then what’s it all about, anyway?”

Meanwhile, Anton, whose job is to synthesize one unified message from the White House, has his work cut out for him. “What’s very clear is that there’s not coordination from the White House,” a former Obama official who served on the N.S.C. told me. “The secretary of state, the U.N. ambassador, the secretary of defense, is saying different things than what the White House is saying.” He rattled off several incidences of Trump officials going off-message: “Nikki Haley went out and said we are committed to a two-state solution after Trump said we were for a one-state solution, Mattis is in Iraq saying we will never take their oil. Tillerson was not even in the bilateral meetings with Trudeau and Netanyahu; that’s very unusual.”

Should the administration get its act together—perhaps via another shake-up, or finally staffing the rest of the positions that reported directly to him—Anton, now Trump’s own “house intellectual,” would be in the unique position to translate alt-right impulses into mainstream conservative-friendly language, and vice versa, hammering out a pragmatic version of Trumpism. It is a vision that, perhaps, Trump has been able to sell to his base in a series of tweets and meandering, emotion-laden sentences, but a vision derided as incoherent and abhorrent among the elite. But he now has Anton, the sophisticated intellectual who can articulate it in a palatable way to the salon-frequenting, port-sipping conservative elites now pulled into Trump’s government, whether they like it or not. And Anton’s job—much like his lodestar, the Florentine thinker who wrapped a diabolical philosophy in the most sublime language—is to make them like it.