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Trump’s Court Jesters

Meet the worst political team ever assembled—an inner circle of outcasts, opportunists, and extremists with nowhere else to go.

Illustrations by Michael Witte

From the start of Donald Trump’s erratic, improbable campaign, political observers of all stripes have been waiting for him to “pivot.” Surely, the thinking went, Trump would eventually set aside the bombast and insults and strive to reassure voters that he could be presidential. “Very shortly,” opponent-turned-supporter Ben Carson said back in March, “I think you’re probably going to see him pivoting more in the direction of everybody, rather than just those who are angry.”

But such thinking always misconstrued Trump’s nature. It’s not just that he approaches politics as a reality-TV series in need of a ratings boost, or that his entire brand is based on an attention-grabbing blend of provocation and hyperbole. It’s that Trump has never been oriented to the idea of a Trump administration. The word, with its implications of organization and stability and control, is the antithesis of what has made Trump a success. As a boss, Trump does not look for established thinkers or veteran insiders to provide him with wise counsel or even a diverse range of opinions. He surrounds himself with peoplemostly white, mostly men, often wealthywho look and sound and think just like him. He is, for all practical purposes, a party of one.

With his showman’s flair, Trump has assured anyone who will listen that he will compensate for his political inexperience and policy indifference by surrounding himself with the “best people.” They’ll be the “smartest.” Not to mention the “greatest.” Unfortunately for Trump, no one with those qualifications wants to work for him. When his campaign approached hundreds of aides to the 16 losing GOP candidatesincluding more than 150 who worked for Ted Cruzthe vast majority passed on the opportunity. When Trump tried to scare up endorsements in Congress, he ended up with a handful of backbench extremists. When he cobbled together a foreign policy team, he couldn’t even find a respectable ex-general from CNN, much less a credible think-tank wonk. When he put together an economic advisory team, he found exactly one willing economist.

So Trump has been forced, for reasons of his own making, to assemble what could well be the worst political team in presidential history: a rogues’ gallery of outcasts and opportunists, has-beens and never-weres, conspiracy-mongers and crackpots. Few of the advisers in his inner circle possess any real qualifications for the positions they hold. Some have been ousted from their previous jobs for incompetence, corruption, or outright craziness. Many, exiled to the political fringes, see the campaign as a way to get back into the game. Most of them, sad to say, have sunk so low that Trump looks like a big step up.

The survey of Trump’s closest advisers presented here does much to explain why his campaign went off the rails in such a spectacular fashion over the summer. Rather than compensate for his own shortcomings, both political and temperamental, Trump has surrounded himself with people who reflect and exaggerate them. It is the mark of a man who feels deeply insecure about his own worth. “Always be around unsuccessful people,” Trump advised his supporters at a rally in Wisconsin, “because everybody will respect you.” But one thing is certain: Whether or not Trump wins in November, there will not becan never bea Trump administration in any meaningful sense of the word. There is, in the end, only Trump. As the candidate himself boasts, “I’m speaking with myself, number one, because I have a very good brain. My primary consultant is myself.”

Correction: The original version of this article said that Schmitz belongs to the Sovereign Military Order of Malta. In fact, he resigned from the Order in 2012.