The middle son of a stony, workaholic father with whom he had an “almost businesslike” relationship, Trump is a double divorcee, a boss with a professed distaste for having partners or shareholders, a television-tethered, hamburger-eating homebody and a germaphobe who has described shaking hands as “terrible,” “barbaric” and “one of the curses of American society.” He’s been a loner most of his life. At New York Military Academy, everybody knew him but few of his fellow cadets knew him well. In college, he made no friends he kept. After he moved to Manhattan, he lived in a sealed-off triplex penthouse, relied on a small, family-first cadre of loyalists and mainly made more enemies than allies (the mayor was a “moron,” elite “so-called social scene” types were “extremely unattractive people,” and on and on). At his casinos in Atlantic City, he was adamant about not mingling with the gambling masses. Now, in Washington, he’s a two-scoops cable-watcher inside the White House when he’s not weekending at his clutch of protective, name-branded bubbles. Trump, forever, has collected an array of acquaintances, fellow celebrities and photo-op props, while friendships mostly have been interchangeable, temporary and transactional.
“He was and is a lonely man,” Jack O’Donnell, a former Trump casino executive, told me.
“One of the loneliest people I’ve ever met,” biographer Tim O’Brien said in an interview. “He lacks the emotional and sort of psychological architecture a person needs to build deep relationships with other people.”