What Trump Really Fears

After decades of giving his top aides autonomy and encouraging them to compete, the president faces an open-ended investigation that may uncover their excesses.

Christian Hartmann / Reuters

As the blast radius of the Russia investigation continues to expand, Donald Trump is facing an unnerving new reality: The fate of his presidency may now hinge on the motley, freewheeling crew of lieutenants and loyalists who have long populated his entourage.

Last week, a subpoena for Trump’s personal attorney, Michael Cohen, was approved as part of the House Intelligence Committee’s investigation into Russia’s interference with the presidential election. With that, Cohen was added to a range of Trump allies who are reportedly entangled in the investigation—from outer-orbit figures like Roger Stone and Carter Page, to more visible senior advisers like Michael Flynn and Boris Epshteyn.

Sources close to the president say there is growing concern in the White House about what skeletons may emerge as investigators comb through a coterie of aides, past and present, who would have done virtually anything to win favor with Trump.

“My fear is that a bunch of people were freelancing—doing things not thinking about the repercussions, but thinking Trump would be so impressed by it,” said one person close to the president. He said that with all the resources the government is putting toward the investigation, “they’re going to want a return.” And in a climate like that, any misguided meeting, bluntly worded email, or undisclosed contact with a Russian official—whether or not Trump himself knew about it—could surface as an incriminating bombshell.

Given the characters this president likes to surround himself with, it’s easy to see why he might be worried.

Long before he entered politics, Trump established a managerial M.O. that came to govern his universe of aides, allies, and hangers-on. Essentially, he populated his team with a cast of scrappy, hard-charging mini-Trumps—people who idolized their boss, and sought to emulate him in every way—and then infused them all with an eat-what-you-kill ethos. Employees are rarely paid impressive salaries at first, but nor are they micromanaged. Instead, they are encouraged to hustle their way up the food chain, competing ferociously with each other to win Trump’s respect, and always seeking out new ways to prove their value.

“He likes to pit advisers against each other,” said one former campaign aide. “He likes the infighting … It’s definitely an environment where you might feel pressured to go the free-range-kid model and say, ‘Hey, let’s see what I can drum up to impress him with.’”

The aide added, “Someone could easily take it a step too far trying to gain something that no one else could gain.”

Chris Ruddy, CEO of the conservative media company NewsMax and a close friend of Trump’s, offered a similar—albeit more laudatory—characterization of Trump’s management style. “He tends to hire strong people … and gives them a lot of authority,” Ruddy told me. That kind of autonomy can produce excellence, he said, but it also comes with risks. “A lot of political campaigns attract real characters and some rogue operators, and I’m sure there were a few running around.”

In many ways, Cohen is emblematic of the Trump theory of management. Fiercely loyal and theatrically thuggish, Cohen embraces his oft-advertised role as Trump’s “pit bull”—routinely issuing outlandish threats against his boss’s critics and enemies. But even as he spent years working out of Trump Tower, people close to him say he never commanded the kind of lavish compensation and cushy perks one might expect for a billionaire’s top attorney. Instead, two sources told me, he made much of his money with a hodgepodge assortment of miscellaneous business ventures—including taxi medallions and real-estate deals—while also dabbling in Trump’s various political and entertainment ventures. He could be cutthroat about maintaining his standing in the inner-circle, and he rarely shied away from an opportunity to protect his turf by bludgeoning his fellow Trumpites. (Cohen did not respond to my request for an interview.)

People who have worked closely with Trump told me it’s not hard to imagine how this environment would lend itself to the kind of unsavory behavior by his aides that investigators are now looking for. Between his sprawling business empire and his chaotic campaign operation, Trump spent 2016 running what was essentially Uber, but for the presidency—overseeing a vast fleet of independent operators for whom the only currency that mattered was gaining an edge for the boss. Who knows how far some of them might have gone to get ahead?

Of course, even if it turns out that Trump was ignorant of his aides’ Russia-related machinations, it wouldn’t automatically absolve him of wrongdoing. Later this week, former FBI Director James Comey is expected to testify that the president sought to influence the bureau’s investigation into the Russia affair—an explosive allegation that, if proven true, would be much more damning than his employees’ misdeeds.

But to those who believe he can weather the coming Comey assault, the biggest remaining X-factor in the Russia scandal is the recklessness and ineptitude that exists in certain segments of Trump’s orbit.

That pattern of behavior doesn’t just provide ammunition to his critics, it also unnerves the president’s allies. One Republican operative with extensive foreign-policy experience pointed to the reports of undisclosed contact between Trump’s aides and the Russians, and wondered if there might be more revelations to come. “If they’re stupid enough to be doing stuff like that, they’re also probably too stupid to realize that there are various [foreign] intelligence agencies … that have the goods on them,” he said. “They’re probably sitting on tapes—what if they get motive to release them?”

Meanwhile, the former campaign staffer went so far as to suggest Trump’s aides could have colluded with Russia without knowing it was illegal. “Is it possible that [Trump] was surrounded with people who didn’t even realize what they were doing was inappropriate? You’d have to be pretty stupid. But there are some pretty stupid people in the Trump camp.”

“You have to remember,” the staffer added, “these people were just kind of in the right place at the right time, and fell into running the country … I would almost compare it to the Keystone Kops. Just silly, maybe well-intentioned people who got lucky—or maybe unlucky depending on how things work out.”