There Are 11 Types of Donald Trump Enablers. Which One Are You?

This week, Cassidy Hutchinson demonstrated in front of the whole world how a political staffer can break free from the rationalizations that lead dwellers of the swamp to enable behaviors we know are evil.

I might be a Cassidy sympathizing Enemy of the People. But as a gay man who contorted himself into defending homophobes and a Trump abhorrer who didn’t hesitate when asked to spin for Trump’s EPA toady Scott Pruitt, I still know a thing or two about being an enabler.

I have had more drinks where reluctant-MAGA and MAGA-adjacent professional Republicans spilled their guts than I would care to count. I’ve heard the lengthy laments from members of the 2 percent about how they’ve got bills to pay, a college fund to fill. Regiments of the “privately concerned” have shared their worries, as have the professionally depressed.

I’ve listened to men bemoan the fact that they can no longer talk politics with their wives; they feel judged by their friends. Been shaken down by the guilt-ridden who wanted to see how they could help our efforts to take down Trump behind the scenes — but were never quite willing to put their name on anything. Been filled with assurances by insiders about how they are needed to keep things on the rails because of all the horrible things I wouldn’t believe they’d prevented, but that they weren’t at liberty to detail.

When you are a prominent Never Trumper and not a total prick, you attract these types of conversations. They weren’t all that dissimilar from the coming-out-of-the-closet convos I’d had over the years. People dealing with their internalized shame. However, in these instances there was one important difference: the realization that they brought it upon themselves.

These conversations became formalized late in the Trump term, once I began writing for Rolling Stone as a sort-of anthropologist to the Trumpists for the Boomer Piketty set. My task was somewhat akin to a National Geographic adventure journalist who embedded themselves in a remote Amazonian rain forest to report back to the mainland about the culture of previously uncontacted tribes. Except the tribesmen were my former colleagues, and the readers shouldn’t have required a middleman’s lingua franca to understand their perspective, because they were unknowingly standing next to them in the Whole Foods checkout line the entire time.

Throughout these informal and professional exchanges, over time, I began to build a reservoir of understanding as to what was going on in the interior lives of the men and women who succumbed to the MAGA wiles. Their hopes and fears and loathings and animal desires.

They all had internalized what they thought were the lessons of the previous decade.  The “political reality” meant that the base of voters in the Breitbart comment section must be appeased and managed. A groupthink emerged whereby this “reality” came to be treated as if it were delivered from on high. And the Truth mustn’t be reflected upon without the whole game being jeopardized.

When I dug deeper beneath this cozy conventional wisdom, what I found were real choices made by individuals who all fell back on a few phyla of rationalization that reveal why they did what they did.

They fit into different categories, some of which reflect universal, human failings replicated across industries and societies and ideologies. Others are unique to the creatures of Washington or the contaminated right-wing political ecosystem that sustained the Mango Monstrosity.

They all turned out to be much more powerful than I had anticipated.

I divide them into these buckets:

• Messiahs and Junior Messiahs
• Demonizers
• LOL Nothing Matters Republicans
• Tribalist Trolls
• Strivers
• Little Mixes
• Peter Principle Disprovers
• Nerd Revengers
• The Inert Team Players
• The Compartmentalizers
• Cartel Cashers

Here’s a field guide, my taxonomy of enablers, so you can identify them in the wild.

First among equals were those with the Messiah Complex. The Jesuses walking among us in their crowns of Apprentice thorns. The messiahs’ self-regard was such that somehow the most grandiloquent leak during the presidency of the world’s most bombastic individual did not actually flatter the narcissist-in-chief himself, but rather the self-appointed messiahs who went to work for a man whose manifest unfitness made them afraid and whose grotesque personality they detested.

In August of Trump’s first year, Axios’s Jim VandeHei and Mike Allen announced the “Committee to Save America,” a “loose alliance” of generals, cabinet officials and high-level staff who took it upon themselves to protect the country from disaster. Among them were National Security Adviser H. R. McMaster, Secretary of Defense Jim Mattis, economic advisers Gary Cohn and Dina Powell and John Kelly, the man who oversaw the implementation of the Muslim Ban from his perch running the Department of Homeland Security before being promoted to White House chief of staff. These self-appointed supermen and wonder women saw themselves mostly in terms of “bad decisions prevented” rather than successes, according to Axios.

You don’t say.

The committee members felt that taking on this oh-so-altruistic act on behalf of America meant that they didn’t have to publicly reckon with the moral compromise of working for someone like Trump. Somehow this justification persisted even after they no longer worked for him and were using their access to make it rain in the private sector. Convenient!

Not a single one of the brave warriors on the Committee to Save America endorsed the only person who could actually save America from Trump — his opponent in the 2020 election.

Despite this logical incongruence, it was the self-flattering messiahs who won the argument among Republicans in D.C. Their demand that “good people” do everything in their power to protect the country from the horrific realities of the president eventually extended not just to those in the national security apparatus but to mid-level political offices throughout town.

From their wake emerged their messianic junior partners who worked as Trump aides and Hill staffers and campaign flacks. They may not have convinced themselves they were saving the world exactly but were justified in the knowledge that if they did not take a glamorous White House job or continue working for a white-bread rational senator, the country would be saddled with someone far worse. Maybe even a white nationalist! Who’s to say? (The fact that a white nationalist might be their replacement did not seem to strike many of the juniors as something that required reflection on the nature of their employment.)

These Junior Messiahs told themselves they were patriots, sacrificing on behalf of the American people, who deserved dedicated public servants like them. This belief was buttressed by the fact that they often had a point: The staffer who would replace them or the politician who would upend their boss in a primary was almost assuredly more terrible. In Trump’s GOP, entropy was taking hold. From the cabinet to the Senate to the school board, the stodgy erudite men of yesteryear were being replaced by ambitious MAGA-fakers who were in turn being replaced by psychotic true believers, giving credence to the conceit that they used to comfort themselves anytime doubt crept in.

The Demonizers were the quickest to drink the Trumpian orangeade as a chaser to liberal tears. For some this was a dogmatic response to any signs of Democratic hostility to people of faith or the free market (or both, for those with the in-home Milton Friedman shrine).

For others, it was cultural, a rejection of the liberal pieties that ground their gears, a discomfort with how fast the script around gender and race was changing. For still others it seemed more personal, emanating from a bitterness over the snooty know-it-allism of the liberals in their life. They clung to anger over the way the left and the media had treated decent Republicans over the years, concluding that, if Mitt Romney and John McCain were going to be tarred as sexist, racist warmongers, then they had no choice but to throw in with the real sexists and racists.

This notion of anger driving support for Trump echoes what a lot of elite conservatives have admitted on the record. Rich Lowry, the nebbish National Review editor (and frequent POLITICO contributor), wrote on the eve of Trump’s losing reelection bid that supporting Trump was a “middle finger” to the cultural left. This seemed to me to be an unbelievably asinine, if understandable, mindset coming from a fussy, middle-aged, Manhattan-dwelling white conservative who resents his more culturally ascendant neighbors. But what caught me off guard was how many of my peers felt the same. Over drinks in Santa Monica, a friend who I had gradually lost touch with over her rabid Trump fandom, stopped me cold when explaining her rationalizations. Despite being a socially liberal, urban-dwelling Millennial, she still had absorbed a deep well of hatred for “woke” culture.

“I just don’t feel the need to drive around my Prius drinking a coffee coolata with a coexist bumper sticker and checking the box like I’ve solved climate change,” she said. “Me moving from plastic to paper straws is not actually moving this needle. The liberal culture of judgment, of do as I say, not as I do. John Kerry flying places in private jets. That’s why I was so drawn to Trump. I was at a breaking point.”

I was genuinely dumbstruck by this. As someone who loves a chocolate shake, I also find forcible paper straw usage to be an utterly moronic inconvenience of modern urban life. But connecting that to support for Donald Trump? Being upset with Joe Biden about private companies switching to deteriorating straws? This anger didn’t click with me at all.

Whatever the underlying reason, these Demonizers have decided that the left, the media, the Lincoln Project, the big-tech oligarchs, the social justice warriors, the people who put they/them pronouns in their email signature, the parents who take their kids to drag queen story hour, the Black Lives Matter protesters and the wokes who want to make stolen land acknowledgments at the start of meetings are all so evil that there is no need to even grapple with the log in their own eye. Trump was a human eff you to the bastards they thought were out to get them. Once you’ve decided that the other side are the baddies, everything else falls into place rather quickly.

Then you had the LOL Nothing Matters Republicans. This cadre gained steam over the years, especially among my former peers in the campaign set. It is a comforting ethos if you are professionally obligated to defend the indefensible day in and day out. Their arguments no longer needed to have merit or be consistent because, LOL, nothing matters. Right? The founder of the Trumpy right-wing website The Federalist, Ben Domenech is, I believe, the one who coined it. He said the LOLNMRs were “inherently fatalist,” believing that the most “apocalyptic predictions about right and left are happening no matter what and that the lights will go down in the West.” Now, from my vantage point, that’s a rather ostentatious way of describing the standard-issue prep school man-child of privilege contrarian cynicism that has been memorialized in teen cinema for ages . . . but you get the point. The LOLNMRs had decided that if someone like Trump could win, then everything that everyone does in politics is meaningless. So they became nihilists. Some eventually took jobs working for Trump; others flipped from center-right normie game players to MAGAfied populist warriors in a flash; still others gave themselves a cocoon of protection working for the Mitch McConnells of the world, staying Trump adjacent so as to not have to challenge their newly developing worldview. But all of them avoided any of the hard questions of the era, wrapping themselves in the comfortably smug sense of self-satisfaction that comes with a lack of concern for consequences.

The professional Tribalist Trolls overlap in their tactics with the Nothing Matters crowd but are different in that they at least have an ethos. Whatever is good for their side is good. And whatever is bad for the other side is good. Simple as that. In the early social media era, I was attracted to this mindset, and for a time when the stakes seemed lower, I was even a member of their ranks. But during the Trump years, I became aghast as it spread like a virus to people’s parents and friends and well . . . some days it feels like pretty much everyone? Or at least everyone who is part of the online political discourse.

If you want to know if you are a Tribalist Troll, ask yourself this — when something horrible happens in the news, does your mind impulsively hope someone from the other tribe is responsible? Nobody wants to admit that they do this. But social media has laid bare our darker angels, and we can now see in real time that a large swath of the participants in our civic dialogue have reduced themselves to the most base type of Tribalist. Veterans of the very online Washington wars have warped themselves to such a degree that every news item, every action, is not something that requires a real-world solution that mitigates the suffering, but is just the latest data point in our online forever war. Many people believe the bullshit they are being sold about their opponents to such a degree that there is an internet culture adage — Poe’s law, which indicates that no matter how over-the-top your parody may be of your political opponent, some of your followers will believe it to be real because they’ve been so conditioned to hear the other side’s awfulness. This insidious Weltanschauung has infected everything from sports message boards to recipe websites to online gaming, which are all now consumed by politicized power users who want to turn every corner of our society into their battlefield. This has created a reinforcing feedback loop up to the politicians and media personalities who are rewarded for constantly embiggening their troll game and expanding the remit outside the bounds of campaign politics. I’ve seen decent people become so warped by this imaginary battle that they began to appreciate Trump’s skill at trolling it even if they were personally repulsed by him. Of all the categories of enablement, this might be the most pernicious and inexpiable.

Naturally, in Washington there are those who don’t need complex ideological justifications for their actions because they are pure old-fashioned Strivers. Some, especially the politicians, are motivated by a blind ambition that is just frankly not that interesting. The fact that pols want to attain higher office so they contort themselves to the whims of the crowd is not a new or unique phenomenon, nor does it merit much deep examination. It’s the first subcategory to the world’s oldest profession. But there’s a uniquely Washington class of Striver that was drawn to Trump like moths to an orange flame. This species doesn’t necessarily want to move up the career ladder for ambition’s sake, but instead, they crave merely the possibility of being “in the mix.”

Every Striver city has a drug that best suits its residents. In New York it’s money . . . and coke. In Los Angeles it’s fame . . . and coke. In Silicon Valley it’s the chance to be a revered disruptor, changer of worlds . . . and microdosing. In D.C. the drug of choice is a little more down-market. All political staffers really want is to be in the mix. It’s not even the power itself that they crave. That would be less pathetic, frankly. It’s the proximity to power. For these Little Mixes, it’s the ability to tell your friends back home that you were “in the room where it happened.” (If it’s possible for an entire body to cringe while typing, that’s what mine did when I wrote “in the room where it happened.”)

Lindsey Graham is the prototypical example of this animal. More than anything, he just wanted to be on the golf cart next to Trump. To be able to pass along a message. To be on the right hand of the father. Whether or not Trump did as Graham asked was merely icing on the cake. He could be denied for months on end to no effect, but if once, just once, he was able to say to his dinner mate that he talked the president into or out of doing something, his heart was made full. He was officially in the mix and no one could take that from him. Washington is full of Little Mixes who don’t get anywhere near the president’s golf cart but are nonetheless omnipresent, sitting in a conference room with Sarah Sanders or being in the back row of a meeting with a cabinet official or staffing a principal in a television greenroom that also contained “the Mooch” or Gloria Borger or some other minor celebrity. Through this access, they get the thrill up their leg that comes with having a story they can share when they go back home over Thanksgiving, about the private moment they saw or heard that makes them feel important. It turns out that’s all they need in life, and it doesn’t matter who the source of power is.

Another Striver subcategory was unique to the Trump orbit: the Peter Principle Disprover. For the uninitiated, the Peter Principle is the business management concept that people in a hierarchy rise to their maximum level of incompetence. In practice, it means a person will be promoted up and until the point where a new skill is required that they do not have. An example is the engineer who becomes a suit and fails because they have to manage relationships and payroll when all they are actually good at is maximizing widget output. Trump’s administration was filled with ambitious Strivers who were punching way, way, way above their weight. People who were promoted three or nine or eleventy million rungs higher than their maximum level of incompetence.

These hacks and maroons would have been nowhere near the Oval Office in any other administration, so they were not going to miss their opportunity to experience the heights of American power and governance just because a bigoted buffoon was behind the Resolute Desk. To understand just how far beyond the Peter Principle the Trump White House had gotten: a man whose previous job was working as a golf caddy was empowered to create international incidents without any management oversight. The White House’s “external relations” director was a 20-year-old Instagram influencer named Camryn Kinsey, who said in an interview, “Only in Trump’s America could I go from working in a gym to working in the White House.” Hard to argue with that, Camryn! Camryn and the caddy mirrored the quality of staff throughout much of the federal bureaucracy, with scores of other enterprising back-row kids taking jobs just because they were not throwin’ away their shot.

The view into the mind of these dolts was captured by Stephanie Grisham, who “served” as Trump’s third press secretary, if you can call her that, given that she never actually held a press briefing. In a jarringly candid interview with New York magazine’s Olivia Nuzzi, during which she acknowledged being part of something “unusually evil,” Grisham said, “My lack of confidence in myself as a single mother and someone who has made mistakes in my past, I thought, well, this is my only shot. Nobody’s gonna ever want me, really, but these people did.” Grisham’s sense of inadequacy was compounded by bitterness toward those who were saying all the things she knew were true about herself and her boss. “You have this sick sense of pride,” she says. “All the people who told you how terrible he was? You’re like, Oh? He’s the [president], buddy!”

The White House was littered with other disprovers who shared Grisham’s combination of ineptitude, imposter syndrome, self-loathing, and bitterness toward their critics but who haven’t acquired the distance from the exhilarating madness to see it as clearly as she does.

The PP Disprover had a marginally more capable counterpart: the Nerd Revenger. You can’t really understand Washington without familiarizing yourself with this prototype. The entire city is made up of sociable wannabes who aspired to sit at the cool kids’ table in high school but were too awkward or unlikable to get the invite. When they got to D.C., things changed. All the time spent obsessing over political redistricting as a teen because their lack of social aptitude left few options for getting laid was finally rewarded. They landed jobs that seemed more interesting than those held by the classmates they had been jealous of and now their younger selves’ dorky little dream was becoming reality.

Take Sean Spicer. Back in college he was a cringey try hard. His roomate recalled that when he walked into a room people would kind of go, “Ugh, Spicer.” The school paper once accidentally printed the staff’s sobriquet for him: “Sean Sphincter,” betraying their true feelings. By the time he got to D.C. things weren’t much different. But in 2011, on the cusp of his fortieth birthday, he earned the title that finally made him bona fide: RNC Communications Director. It was in this spot that Spicer finally got to become the man he always thought he should be. At long last he would be the one whom other aspiring party functionaries needed to befriend if they wanted a seat at his table, rather than the other way around. So when the White House came calling, it didn’t matter that Spicer had hailed from the party’s establishment wing. He was happy to put up with Trump’s lunacy as long as he became a star. After all, when you’re a star, they let you get away with anything.

As he told Jimmy Kimmel, “I’ve never had a boss I represented where 100 percent I agree with what they believe. That’s not the job you sign up for. You’re not saying, ‘I’m going to agree with you.’ You’re saying, ‘I’ll do the best job I can communicating the thoughts and ideas and beliefs that you have.’” He didn’t see anything wrong with shining a poison apple. He got nearly everything he ever wanted. And you’d better believe he’d do it all over again.

Of course, not everyone in the Trump universe had some revenge fantasy to play out. Some just lacked the imagination to conjure what else they could do with their lives. These Inert Team Players couldn’t fathom another option besides taking the next step up the political ladder. Many are so wrapped up in their identity as a Republican that the idea of being anything besides that is inconceivable. They had been college Republicans and they go to Republican bars, they have Republican LinkedIn handles, and, hell, some even have Republican tattoos. I know multiple people in GOP politics who named their daughters Reagan. For many people in Washington, their party is more a part of their identity than their ethnicity, religion, or personal history. It’s how they see themselves and how everyone in their social network defines them. Shedding an ingrained identity that others use to define you takes courage, even if that identity is toxic and self-destructive. All of this makes the bar for removing “Republican operative” from a person’s identity pretty hard.

Throw on top of that the fact that Republican politics is how they made a living and they still opposed tax hikes and abortion and you can see why people were reluctant to cut bait.

If they were going to envision a new identity for themselves, they needed the wake-up call that I got as a closeted Republican when I realized it was a future tapping my foot in an airport bathroom I needed to fear, not what my friends and family would think when I told them I was gay. Most were in too deep and their thinking was too rigid to recognize that their escape hatch was through Trump’s wide stance.

Instead, these Team Players kept their day jobs, but unlike the Strivers, their distaste for the president resulted in receding a bit from the social scene. Scaling back their ambitions. Over time, the sharpness of the moral sacrifice dulls. They consider themselves one of the “good Republicans.” And as the years go by, they become increasingly less and less likely to make a dramatic identity-altering gesture. Then, one day, they are editing a press release that expresses concerns about the electoral count in Pennsylvania and wondering what the hell they are doing with their life.

But they still had kids and mortgages and would end up reverting to what they know, like a midlevel oilman who trudges back into the office the day after a spill. What else am I supposed to do? they would ask me. (I would proceed to make a series of suggestions that were rebuffed.)

The Compartmentalizers were the Inerts’ more anxiety-riddled peers. As the onetime Compartmentalizer-in-Chief, I can grok these folks’ motives the most clearly. Many of them agonized over sticking around. They would tuck bad Trump thoughts in a box in the corner of their brain somewhere and go on with their duties, clocking in and clocking out as required. Work that had once enlivened them had become a miserable chore, with sporadic bouts of gratification. They cut back on news consumption, trying to mentally check out as much as possible. Some picked up new passions away from work; for others the new passion was an alarming increase in their intake of wine, an old passion. Anything to keep the moral quandary of providing aid, however indirectly, to Trump from emerging from their hippocampus. Every other month or so the bad thoughts would spring from the dark recesses of their brain. “Very fine people on both sides.” Bang. “Helsinki.” Bang. “Send them back.” Bang. And each time their self-loathing would eke out for a day or a week before it got sent back to the lockbox, and they reverted to their old habits.

Finally, I would be remiss to ignore the most common and obvious motivator for this or any ethically dubious endeavor: money. One big misconception about Washington is that money is the straw that stirs the drink. Activist types always demand we look to the money! Sometimes they are right, but the driving motivator for most during the Trump era was not a desire for riches. This town is not filled with Gordon Gekkos. More often, it’s the other, more egocentric motivators that drive nefarious actions in D.C. Raising money remains important, but fundraising is really about status and power. Yet there were a handful of entrepreneurial Republicans whom most people have never heard of who did enrich themselves beyond their wildest imaginations during the Trump years. These Cartel Cashers now spend time designing their beach compounds, the spoils of their sacrifice.

Just look at the cartel-cashing couple, Mike Shields and Katie Walsh. Shields advocated for pushing the Republican Party toward the center after Romney’s defeat in 2012, and friends of mine tell me Walsh cried when Trump won on election night in 2016. But that didn’t stop them from riding the Trump train to fortune. With Shields running a super PAC focused on electing Republican House candidates and Walsh serving as Reince Priebus’ chief-of-staff they managed to thrive in Trumpworld, walking the MAGA/establishment tight-rope, utilizing leverage and relationships and powered by pride in the work that had gotten them there.

As I called around to their friends and former friends trying to understand why they did it, the answer kept coming back to the quid. A fellow consultant who knows the game explained the motivation rather simply.

“Shields had never been in a job that made more than two hundred and fifty thousand dollars a year in his life,” he told me without irony. “This was his opportunity.”

Only a quarter-million bones? Where is Friar Tuck when you need him, this might require alms for the poor!

Most people don’t fit neatly into a single category. Some had a little from column A and a little from column C. There was a jumble of rationalization blended in with their best intentions and their shadow wants. But you know a type when you see it.

Consider Chris Christie: a Little Mix and Team Player and Junior Messiah all wrapped up in Costco Club packaging. Christie is a Churchill in his own mind but was turned by Trump into a sniveling church mouse.

For years Trump demeaned and diminished Christie at every turn. He threw away the transition plan he wrote after the election, passed him over for jobs, and made him into the family’s personal gimp, to be summoned from his shackles on command.

You might think that someone with Christie’s ego would eventually have walked away from this type of torment. But no. Ever the glutton for being in the mix, he kept coming back for more.

Toward the end of the 2020 campaign, at the height of the COVID-19 pandemic, Trump unshackled him one more time, demanding he play the role of Biden in the president’s debate prep. Months later it was revealed that the president had tested positive for COVID before these sessions began, but kept it a secret, holding Christie captive in close quarters for days, brazenly spittling diseased airborne droplets all over him.

Soon after, the sub contracted his dom’s virus and spent a few harrowing days in the intensive care unit, where he genuinely feared he might die. When Trump called Christie in the hospital, as he lay on death’s door, Trump’s only concern was whether the little mouse would have the courage to publicly blame the sickness on him before election day or would keep running cover for his master.

The depraved indifference! The collaring! How does a man accept such despicable treatment and maintain even a modicum of self-respect?

Unlike the millions of others who were not so lucky, Christie managed to come out the other side. But that doesn’t change the fact that Donald Trump nearly killed him with the same abject, megalomaniacal recklessness he had subjected upon the entire country with his management of the pandemic. The president was so hell-bent on minimizing the threat of COVID-19 — and demonstrating his imagined ubermensch virility — that he put Christie and the hundreds of others he encountered while contagious at risk.

And yet when Christie returned from the hospital, rather than stand up for himself, rather than get angry, he waddled right back into the clutches of his patient zero, supporting his reelection campaign.

At the time of this writing he continues to maintain that he has not ruled out going back into the breach for Trump one more time should the latter be the Republican nominee for president again in 2024.

That shows you how powerful the complexes that afflict these enablers are. They persist even in the face of a near-miss visit to St. Peter at the Pearly Gates.

Christie’s particular motivations, and those of my other former colleagues who knew better, might be somewhat different, but all roads led to the same Trumpian hell.

Adapted from Why We Did It: A Travelogue from the Republican Road to Hell, by Tim Miller. Copyright © 2022 by HarperCollins Publishers.