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A few weeks into the Trump administration, I overheard a friend who works in publishing remark, “Possibly the only good thing that will ever come of this is a bunch of tell-all memoirs that will be a lot juicier than the typical White House book.” That prediction, rather like a Trump campaign promise, has yet to be fulfilled. Exposés of the dysfunctional inner workings of the Trump White House have reaped plenty of cash for the book business, but the best dish has mostly come from outsiders, journalists like Michael Wolff (2018’s Fire and Fury), Bob Woodward (2018’s Fear), and Washington Post reporters Carol D. Leonnig and Philip Rucker (this year’s A Very Stable Genius). Books by former Trump staffers—of which John Bolton’s headline-making The Room Where It Happened is the most recent—tend to be stunted, partial accounts, twisted like bonsai trees by the authors’ needs to make excuses, cover their tracks, and justify choices that in retrospect look poor indeed.
But taken all together, these staffer memoirs offer a sense of something that no outsider can ever completely understand: what it’s like to live in Trump World. That’s what its denizens call the alternate reality surrounding our petty, distractible, praise-hungry president. Under its spell, people strive to gain and hold onto their perches in what has to be one of the worst workplaces in the history of the ruling classes, short of Caligula’s Rome. The Room Where It Happened contains its share of outraging scoops, thoroughly covered elsewhere, and is as replete with pontification, chickenhawk saber rattling, and numbing notebook dumps as its initial reviewers have attested. But it also provides the public with yet another facet of the mad tea party that is Trump World.
Bolton replaced H.R. McMaster, who had been forced out as Donald Trump’s national security adviser, and whose own memoir is due in September. According to A Very Stable Genius, by the end of McMaster’s tenure, Trump had taken to imitating McMaster behind his back by puffing up his chest and barking in a “fake shout like a boot camp drill sergeant.” Bolton claims that he went in with “no illusions” about his ability to change Trump, perhaps believing that his frequent quoting of Eisenhower, Cato the Younger, and Thucydides would at least succeed in shaping policy. In this, he firmly belongs to the White House contingent he names “the axis of adults,” officials with experience in governing who sought to direct Trump’s wayward impulses and uninformed notions into some kind of consistent leadership. But Bolton insists that these people (a group that presumably includes such figures as former Secretary of Defense James Mattis, former Secretary of State Rex Tillerson, and McMaster) failed because they “didn’t do nearly enough to establish order, and what they did do was so transparently self-serving and publicly dismissive of many of Trump’s very clear goals (whether worthy or unworthy)” that Trump became mistrustful of his advisers and “saw conspiracies behind rocks.” Bolton did succeed in ticking off a few items on his to-do list, most notably the U.S. withdrawal from the Iran nuclear deal—an obsession of his, as is everything Iranian—but eventually he got on everyone’s nerves and was fired in September.
The Trump White House has to be one of the worst workplaces in the history of the ruling classes, short of Caligula’s Rome.
In opposition to the “adult” staffers who deluded themselves that they could manage Trump are the believers, who have published their own set of memoirs. These include staffers like former press secretary Sean Spicer, communications aide Cliff Sims, and Trump satellite Chris Christie. Of these three, Spicer voices the fewest reservations about Trump’s management style. At times, in his 2018 memoir, The Briefing, his obeisance verges on Stockholm syndrome. After only six months in the White House, Spicer was effectively pushed to resign when Trump hired Anthony Scaramucci over him as communications director, the position Spicer had been seeking since the campaign. “This is the change you need and deserve,” he said to the president when handing over his resignation letter. “OK, if that’s what you think,” was Trump’s reply, prompting Spicer to rhapsodize about having seen a side of the president that is “caring, kind, and gracious.” (Scaramucci lasted only 11 days but got his own book out of it anyway—one that was so slim that, as with Omarosa’s, even I could not be bothered to read it.)
Christie grovels a bit less, having known Trump since the days when his political aspirations looked like nothing more than a publicity stunt. After the Bridgegate scandal scuttled Christie’s own presidential ambitions, he became an early Trump endorser, claiming, in his 2019 memoir, Let Me Finish, that he recognized that Trump “was everything I was, but on jet fuel.” Trump commandeers Christie’s memoir, with Christie’s own career taking a back seat to his herculean efforts to come up with the campaign’s 30-volume transition plan, only to see it dumped in a trash can by Steve Bannon. Let Me Finish could just as easily be titled I Told You So, so often does Christie return to the plan as rosy phantom of what might have been. Trump strung Christie along for months with promises that he might be made vice president or attorney general, before snatching away the prizes and offering instead such lesser roles as secretary of labor and ambassador to Vatican City.
Dangling and withdrawing goodies is a classic Trump move, one he used repeatedly on Bolton. He relishes a drawn-out interviewing process that requires petitioning luminaries to come through various Trump HQs like contestants in one of his beauty contests as the media breathlessly speculates on every visitor. Another Trump standby is keeping officials at postings in an “acting” capacity so that they must constantly court his favor instead of telling him facts he doesn’t want to hear.
While it is in many respects a vile object, Cliff Sims’ Team of Vipers, a 2019 account of Sims’ 500 days in a relatively minor White House job, probably offers the clearest picture of Trump’s management style. “This is my Wilbur,” Sims observed Trump saying as he introduced Secretary of Commerce Wilbur Ross to Egyptian President Abdel Fattah el-Sisi. Sims, who generally takes a positive view of Trump despite having been burned by him, notes that the first-person possessive is a term the president reserves for those with whom he feels a “special connection.” More accurately, it reflects the fact that, in Trump’s mind, he doesn’t so much hire staff as obtain them like trophies for display.
Trump went on to boast to Sisi that Ross is “so famous on Wall Street, all you have to say is ‘Wilbur,’ and everyone knows who you’re talking about.” Despite what his supporters often praise as a maverick independence from “elites,” Trump could not be a more slavish credentialist. He betrays his credulous investment in conventional opinion every time he rattles on about what “people” or “everyone” is “saying,” and the class that dispenses prestige and Ivy League degrees, or talks about “Wilbur,” is the same class his base adores him for appalling. Similarly, the term “central casting” comes up a lot in the accounts of Trump staffers. “You’ve got to understand, Chris,” Trump told Christie when he picked Mike Pence as his running mate. “He’s out of Central Casting.” Sims describes the two words as Trump’s “favorite phrase,” because for the president, “looking the part was every bit as important as doing a good job.”
Like many a terrible boss, Trump is fundamentally a coward.
Meanwhile, Trump is forever asking his staff for impromptu performance reviews, particularly negative ones, of other staffers. “He couldn’t even complete a sentence today without stuttering,” Trump once told Sims of Spicer. “What do you think about Sarah Sanders? Would she be better?” Most Trump World memoirs feature several conversations like these. This passive-aggressive move is manifestly designed to make everyone feel as insecure and paranoid as he does, but believers like Sims, Christie, and Spicer seem oblivious to Trump’s intent, persuading themselves that scheming colleagues alone were responsible for the misery of their workplace. It’s not until Sims decides to fink on a co-worker he suspects of leaking unflattering information to the press and Trump calls for a pen and paper so that he can start taking down names for what Sims calls an “enemies list” that the aide gets an inkling that this fish may be rotting from the head.
Like many a terrible boss, Trump is fundamentally a coward. In direct contrast to the image he cultivated on The Apprentice, he rarely has the nerve to fire anyone to their face. More often than not, he uses belittling treatment and other indirect means (such as hiring Scaramucci over Spicer) to force them to quit. Or he simply announces their replacement on Twitter, as he did to Tillerson. Trump may lose his temper and berate his underlings, but exercising calm, considered, and deliberate authority is another matter.
This insecurity lies at the root of Trump’s fascination with autocrats like Vladimir Putin and North Korea’s Kim Jong-un. He envies not just their totalitarian powers but the ease with which they wield them. According to Sims, one Trump biography claims that Trump’s father, Fred, used to intone to his sons, “You are a killer. … You are a king. … You are a killer. … You are a king.” As a result, “killer” became “the single highest compliment” in Trump’s pantheon. He praised his Wilbur as a “killer” and Kim, as well. In Kim’s case, it is the literal truth. “He was like 26 or 25 when his father died,” Trump is quoted saying in A Warning, the 2019 book by an anonymous senior official, “and all of a sudden … he goes in, he takes over, and he’s the boss.” By Bolton’s account, Trump’s infatuation with Kim took on the bizarre quality of a teenage crush. The president proclaimed that the two had “fallen in love” and fussed for months about delivering a gift to the despot: a Trump-autographed Elton John CD.
That this strange courtship followed closely on the heels of a nerve-wracking incident in which Trump threatened North Korea on Twitter with “fire and fury like the world has never seen” underscores just how capricious this presidency has been. In an interview with ABC News’ Martha Raddatz, Bolton said that he could discern “no coherent basis, no strategy, no philosophy” in the White House. “Decisions are made in a very scattershot fashion.” This is partly because, as Sims puts it, Trump believes himself to function comfortably in chaotic conditions that leave his adversaries at a disadvantage. But in what sense can the president’s own staff be considered his adversaries? Who makes an enemies list of the people working for him? Is Trump really so threatened by “his” prized pet generals and assorted “killers” that he needs to keep them in what Bolton describes, with a hilariously gratuitous display of Latin, as a “Hobbesian bellum omnium contra omnes (war of all against all)”?
Yes, probably, but these memoirs also suggest that Trump doesn’t trust some members of his administration because he simply doesn’t understand them. Their behavior springs from a commitment to principles he not only doesn’t possess but can’t. Some of these principles have to do with morality, which Trump lacks, but others require a long-term or big-picture perspective of which he also seems incapable. According to Bolton, Trump “believed he could run the Executive Branch and establish national-security policies on instinct, relying on personal relationships with foreign leaders.” Everything is personal and therefore ephemeral. Even without the shit-stirring that Trump regularly engaged in with his staff, his fundamental rudderlessness can only have left them to their own devices and at cross-purposes with one another.
This blind spot also put Trump on a collision course with not one but two G-men, James Comey and Andrew McCabe, authors of the two most readable books about working under Trump. In their notorious discussion during which Trump asked, improperly, for Comey’s “loyalty,” the FBI director’s hedging counteroffer of “honesty” led Trump to jump to the conclusion that they’d reached a deal: Comey would provide him with “honest loyalty.” As Comey sees it, his primary commitment is to the truth—the title of his 2018 memoir, A Higher Loyalty, refers to this—but such abstractions mean nothing to Trump. He blows past them as so much meaningless babble. Loyalty, however, is personal, and that he gets.
Both FBI directors are ideally positioned to compare Trump to a mob boss—but, really, isn’t this an insult to mob bosses?
McCabe, who succeeded Comey to become acting director of the FBI, is less philosophically inclined than Comey, but he was fiercely devoted to the FBI, where he had worked for more than 20 years. Both Comey’s book and McCabe’s—The Threat, published in 2019—feature dramatic backstories about investigating organized crime and terrorism, which are a lot more entertaining than tales from Spicer’s early work on political campaigns or Christie’s time running for the board of freeholders in Morris County. Comey in particular has a fine eye for revealing character traits, noting that, while Presidents George W. Bush and Barack Obama always met with him while sitting in armchairs by the fireplace in the Oval Office, Trump made a point of sitting behind the famous Resolute desk, as if girding himself with an authority he felt unable to assume without it.
For his part, McCabe witnessed some of the president’s most flagrantly vindictive pettiness. Trump insisted that the FBI’s investigation of Hillary Clinton’s emails was tainted because of donations McCabe’s wife received for an unsuccessful political campaign in Virginia. During a telephone call, Trump told McCabe to ask his wife “what it was like to lose. It must be tough to be a loser.” Later, after taunting McCabe on Twitter for “racing the clock to retire with full benefits,” Trump had Attorney General Jeff Sessions fire McCabe less than two days before his pension was fully vested.
Both Comey and McCabe have backgrounds that ideally position them to compare Trump to a mob boss—but, really, isn’t this an insult to mob bosses? Running an extensive and ongoing criminal enterprise requires a consistency and an accountability to one’s underlings that Trump has never exhibited. And as Sims ruefully puts it at the end of Team of Vipers, “He hadn’t lifted a finger for countless loyal aides before me, and I’m sure he wouldn’t for countless loyal aides to come. It was well known that in Trump World, loyalty was mostly a one-way street.” Mafiosi may impose primitive honor codes, but as Comey observes with no small fascination, these are nevertheless codes that apply to everyone. How long could a mob boss as capricious and untrustworthy as Trump last before his lieutenants revolted and replaced him with someone more competent?
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