Later, in the car, he kept looking in his rearview mirror.
“I’m so spooked,” Taylor, a former Trump Homeland Security Department official, recalls during an in-person interview that he agreed to participate in only after many assurances that the location be kept secret.
Not long before his close encounter with the drone, Taylor had earned a measure of national attention by endorsing former vice president Joe Biden, the Delaware Democrat, in the 2020 presidential election, joining the cavalcade of "formers" to publicly put their names to criticism of an often unhinged White House.
He’d been a chief of staff at the Department of Homeland Security and forever Republican, but was mostly unknown outside wonky Washington circles until then. Now people were recognizing him.
In late October, Taylor went even further, revealing himself in a Medium post, after more than a year of furious speculation and repeated denials, as “Anonymous,” the author of a much-discussed 2018 op-ed in the New York Times describing a stealth understory of resistance inside the Trump administration made up of officials bent on frustrating the president’s most ridiculous and dangerous instincts.
At the same time, Taylor fessed to writing the 2019 book, “A Warning,” which presented an even darker portrait of a president who had turned out to be nearly impossible to restrain. President Trump has talked of a nefarious “deep state” conspiracy of career government operators determined to topple him. Taylor has a different take, saying a “steady state” of political appointees and career employees were intent on stopping the president from harming the country.
In the weeks since Taylor’s self-induced unmasking, he has shuffled between at least 10 undisclosed locations, he says, bunking in private homes and hotels after receiving a deluge of death threats. Haters on the political right despise him, nudged along by Trump calling him a “traitor.” Haters on the left demean him for staying more than two years in an administration they consider corrupt and amoral, and for working at a Department of Homeland Security notable for its inhumane immigration policies — positions that he says he did not support and sought to soften.
Worried that he’ll be attacked, Taylor now employs private security. One recent afternoon, a large, stern man guarded the entrance to the location where Taylor has holed up for the day. Inside, Taylor stuffs rolls of toilet paper into a backpack because he’s close to running out at one of his other places of refuge.
Taylor, despite the drama, remains the relentlessly affable, eager-to-please charmer who rose so absurdly quickly through the ranks of staffers in Washington. At 33, he could easily be mistaken as a mid-20-something. His brown hair is swept back so meticulously and abundantly that it almost dares you to muss it. His right eye is blue and his left is green, he notes, cheerfully, brandishing a toothy smile.
In his travels to battleground states to nudge Republicans away from Trump, Taylor laments that he’s put on a few pounds. By all appearances this claim is dubious as he offers it up while perched in a slender-fitted jacket.
“It’s all kale salads now,” he says.
When he ventures out of his hiding places, Taylor favors baseball caps pulled low and sunglasses. A mask serves the dual purpose of shielding him from infection by the coronavirus and concealing an identity that has become ever harder to camouflage as he’s upped his public presence by serving as a CNN contributor and talking head.
“There’s no better time to be anonymous,” quips the man who once was “Anonymous.”
The mysterious author named Anonymous was a player, a self-appointed early-warning system about Trump’s presidency. People listened to Anonymous.
As a device, it was genius. The intrigue about who might have written it — and the speculation that it might have been someone far above Taylor’s rank, perhaps even a member of the Cabinet — gave a then-shocking (though now commonplace) revelation all the sizzle that it would never have received if he’d put his name on it.
“Who the hell is Miles Taylor?” he imagined people would have said.
Now, come into the light, Taylor would like to be a Republican Party thought leader, he says, offering, along with fellow Trump dissenters, “a rational voice within the party to steer the GOP back to principles-based governing, and away from the cult of personality around Donald Trump.”
“We’ve got to get back to what it stood for — free minds, free markets, free people — and to give Americans a more hopeful vision of the future.”
Yet a question lingers behind the smile and the telegenic glossiness: Will the people who listened to Taylor when he was Anonymous listen to him now?
There's an of-course-he-did thread that runs through the evolution of one Miles Taylor.
Of course, he went to an elementary school set in a Midwestern cornfield. Of course, the future fast climber at the Department of Homeland Security came to Washington as a teenage page in the House of Representatives. Of course, he landed the most-coveted page assignment: Working for then-Speaker Dennis Hastert, the Illinois Republican. Of course, he dazzled, and sometimes put off, his new friends and the higher-ups with his energy, all-too-apparent ambition and overachiever’s enthusiasm — for everything.
“He takes you off-guard. Is this an act?” Taylor’s longtime friend James Barnes, a fellow page who is now a noted digital campaign strategist, remembers thinking. “It’s not an act.”
Taylor had grown up a child of divorce, with a bifurcated existence, in the northwestern Indiana town of La Porte. A bottomless repository of historical, literary and philosophical minutiae, he helpfully points out that the town took its name from the French for “door” — because it led to someplace else.
His father, Ted Taylor, was a prosperous insurance agent; his mother a struggling school nurse. At dad’s, life was comfy; at mom’s it wasn’t. Her house occasionally went dark because she couldn’t pay the electric bill, Miles Taylor says.
The future shaper of Washington policy nerded out as a sixth-grader researching the intricacies of policies related to extreme poverty. He got a job writing scripts at a tiny radio station; one day his dad tuned in, and to his surprise, heard his son’s voice. The next thing he knew, Ted Taylor was driving his precocious son to news conferences.
Taylor and much of his family are Republicans, but their bloodlines trace to the other team. His grandfather, William Taylor, was a moderate Democrat who served in the Indiana Senate in the 1960s. (Miles Taylor, though an avowed conservative Republican, donated to Democrat Barack Obama’s 2008 campaign, a decision he made, in part, because of the history-making prospect of a first African American president.)
They’re practical folk, these Taylors. When Taylor went off to study philosophy and international relations at Oxford years later, his father bought him a pair of clippers so he could save money by cutting his own hair. Taylor figures he’s saved $4,000 over seven or so years.
When Taylor got married a few years ago, his then-fiance gave him an ultimatum, he says: Get a professional haircut or she wouldn’t show up at the altar.
He did what he was told.
Taylor wasn't a Trump supporter, still, he parlayed his experience on the House Homeland Security Committee into a job in the Trump administration, first serving as a counselor to one of his biggest boosters, the president's chief of staff, retired Marine Gen. John Kelly, and then at the Department of Homeland Security.
Among Washington strivers, lofty aspirations often crash into ugly, maddening realities. Taylor found himself quickly enmeshed in the turmoil surrounding Trump’s legally flimsy fixation on banning travel to the United States by people from an array of predominantly Muslim nations. In Sept. 2017, Taylor — then a DHS counselor — told reporters the plan being recommended to Trump by acting DHS secretary Elaine Duke would be “tough” and “tailored.”
Taylor earned a reputation within the department as boundlessly ambitious, rankling some of the more experienced hands, and pushing for promotions, according to two former high-ranking DHS officials who spoke on the condition of anonymity to relate private conversations. Others admired his initiative, as he rose to deputy chief of staff, then chief of staff.
Behind the scenes, Taylor argued for limiting the number of countries affected by the travel ban, Taylor and his-then colleague Olivia Troye say in interviews. In meetings, he sometimes clashed heatedly with Gene Hamilton, an attorney working on security issues at DHS who is now at the Justice Department, and had a reputation as an immigration restrictionist. Taylor argued for relying on data about which countries cooperated with the United States to determine who was banned. Troye, who would later make news by resigning and accusing Trump of putting his reelection effort ahead of public safety in the pandemic, remembers walking away from one dust-up and thinking, “Okay, Miles isn’t crazy.”
“Bless the heart of anyone claiming that Miles and I ever had a heated discussion about anything or an actual disagreement about any particular list of countries,” Hamilton says. “Any such claims are totally false.”
In private, Taylor says, Trump was pushing DHS to recommend expanding the countries covered in the ban from around half-dozen “to double, triple, quadruple the number.”
While fighting to frustrate that effort, Taylor felt like he and like-minded DHS staffers had become the much-hoped-for guardrail on Trump.
“If we weren’t there,” Taylor says, “there would have been a travel ban on dozens of countries.”
Miles Taylor wanted out. But he wanted company.
He envisioned a dramatic en-masse resignation, including Cabinet secretaries and their top aides, to prove the point that Trump was unfit for office.
Two months before the midterm congressional elections, Taylor was infuriated when Trump wanted flags that had been lowered to half-staff after the death of iconic Republican Sen. John McCain of Arizona to be lifted. While on a work trip to Australia, he dashed off a short op-ed that the Times agreed to publish anonymously, a condition Taylor wanted because he hoped the focus would be on the issues he raised rather than him. Even the headline made headlines: “I Am Part of the Resistance Inside the Trump Administration.”
Taylor is coy about how many people knew it was him.
“Fewer than the fingers on your hands,” he says.
He didn’t even tell his wife until “many months later,” he says.
After finally resigning in 2019, Taylor ensconced himself in his grandmother’s condominium on Marco Island, Fla., to write. His family wondered what he was up to.
By Nov. 2019, he had a book that, despite its mostly pedestrian writing and tangents about philosophers, became a bestseller because of its content. The book’s examples reinforced everything that Trump’s opponents feared about him, including calling out Trump’s “truly insane” suggestion that people detained for illegally crossing the border be sent to the U.S. prison at Guantánamo, Cuba, a facility that houses notorious terrorists.
The book is generally hyper-cautious about singling out Trump administration officials, other than a few, such as immigration extremist and presidential sidekick Stephen Miller. Taylor didn’t want it to be tell-all, but he takes a few shots, including an obvious bolt against his former boss, the much-criticized former DHS secretary Kirstjen Nielsen, who had defended Trump’s policy of separating families detained at the border. Without mentioning her, Taylor writes with disdain about “homeland security leaders who in a sickening display of bad judgment, conceded to a policy that increased the number of children ripped from the arms of their parents at the US-Mexico border. It left a stain on their reputations, their department, and the country.”
Taylor was furious that Trump’s White House “threw Nielsen under the bus” by talking her into publicly defending the policy, which she’d been privately arguing against.
Taylor says he delegated most immigration policy work to underlings and focused instead on national and international security issues, including — foreshadow much? — “dangerous drones.” But he doesn’t entirely absolve himself.
“I wish I’d gotten more invested,” he says.
Proximity to Trump’s policies would haunt Taylor.
When he later landed a national security-related job at Google, a Muslim advocacy group, MPower Action Fund, posted an open letter urging the company to fire him, and calling him “racist” and “xenophobic.
Google, it seems, was unmoved. Taylor kept his job.
On the evening of Oct. 28, Trump took to Twitter and did what he has done so often during his time in office: He lied.
Taylor had just revealed himself as Anonymous, and Trump told his tens of millions of followers that he’d “never even heard of” Taylor. (Trump had, in fact, mentioned Taylor by name in August when he wrote a critical op-ed in The Washington Post and endorsed Biden for president, tweeting that Taylor is “said to be a real ‘stiff.’ ”) At a campaign rally, Trump called Taylor a “sleazebag” and a “low-level lowlife” who should be “prosecuted.”
The revelation of Taylor’s identity came as a surprise to his father. One of the first things he did was order a copy of his son’s book.
The New York Times took a little heat for calling him a “senior official,” though Taylor was able to mostly swat that away by pointing out that he was, after all, the deputy chief of staff, at the time, for a department with more than 200,000 employees and that the Trump administration had tasked him to give background briefings to the media as a “senior official.”
He also got slapped around a little for having denied being Anonymous in an on-air CNN interview, the network where he is now a contributor. It’s not the first time, however, that an “Anonymous” has falsely said he wasn’t Anonymous. Remember the denials from author Joe Klein when he anonymously wrote the buzzy book inspired by Bill and Hillary Clinton, “Primary Colors”?
Defeating Trump became an all-consuming endeavor for Taylor. He co-founded an organization dedicated to reinventing the GOP called, the Republican Political Alliance for Integrity and Reform (RePAIR), which boosts some boldface conservative names, such as prominent foreign policy veteran Richard Armitage, former acting attorney general Stuart Gerson and an assortment of onetime members of Congress.
Taylor envisions the group “undoing the damage” of Trump’s tenure in office, and “advancing a more compassionate and ideas-based GOP platform.” Now, he says, “folks see the party as soulless, greedy and inhumane.”
Spooling it out, he sounds a little like a future candidate for public office. Asked whether he’d run, he doesn’t say yes. He doesn’t say no, either.
Taylor might “play a role” in guiding the party’s new era, says a former Republican member of Congress who has worked with him. But the former lawmaker — who spoke on the condition of anonymity to discuss candidly his, and others’, expectations for a colleague — is quick to relegate him to a lower echelon in the status-conscious political hierarchy, noting he was merely “a staffer,” not an elected official.
Taylor had taken a leave from his Google job during the campaign as he hopscotched battleground states urging Republicans to vote for Biden. He won’t be going back to Google. He won’t go into details, but describes it as an amicable departure.
He’s out of work, except for the part-time CNN employment and some consulting projects, and his finances are in tatters — he has said he’ll donate much of his book royalties to organizations, including the White House Correspondents’ Association. And he’s had serious marital problems.
On the Saturday after the presidential election, Taylor says a friend called him. The friend had news: The networks had declared Biden the winner of the presidency.
Taylor, a man of oceanic words, was speechless.
Moments passed before the silence broke.
Miles Taylor was sobbing. They were tears of joy.