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?