Early on, Trump had greater self-control than he had as a candidate, but he couldn’t quite crack the likability factor—and, maybe, he didn’t want to. Long before Tony Soprano launched the anti-hero drama, Trump was that guy. He was a handsome go-getter, but also an arrogant self-promoter, proud of his toughness, a flirt with a fat wallet. On “60 Minutes,” he complains about media coverage. “I believe they like to make me out as somebody a little more sinister than I really am,” he tells Mike Wallace. “I don’t look at myself, necessarily, as being sinister.”
In 1990, Trump appeared on a game show called “Trump Card,” set at Trump’s Castle, in Atlantic City. As his life became unstable, rocked by divorces and bankruptcies, his TV persona stayed flush. He made cameos on sitcoms: on a 1994 episode of “The Fresh Prince of Bel Air” (Carlton faints in admiration); on a 1996 episode of “The Nanny” (he dates Fran). In 1999, he ruined a perfectly good episode of “Sex and the City.” In these incarnations, Trump is a Manhattan fixture. And yet it feels as though he’s shrunk to a fun-size Trump: red tie, yellow hair, “the Donald.” He’s less an icon than he is a retro cartoon.
By the turn of this century, in the eyes of New Yorkers, all that remained of the once powerful developer was his logo. This was when he began to reinvent himself as a star in new genres: reality television, pro wrestling, and cable news, particularly Fox News. These combative art forms suited his style—flamboyant and vaudevillian. When Trump first entered TV, the entire medium had been dismissed as junk. Now, even as critics were swooning over the artistry of cable drama, Trump swerved deeper, into stranger regions, straight into the types of television that nobody took seriously, the ones dismissed as guilty pleasures.
When Burnett pitched Trump to NBC, it was as the host of only the first season of “The Apprentice”; after him, new tycoons, including Mark Cuban and Martha Stewart, were supposed to step in. According to the book “Trump Revealed” (2016), by Michael Kranish and Marc Fisher, the plan quickly changed. Trump’s comfort on camera, his ability to improvise—including the “You’re fired!” tagline—cemented his value, as did the strong first-season ratings. Burnett conceived of the show as “Survivor” in the “urban jungle,” and it became NBC’s flagship. Trump’s relationship with viewers was transformed: “He was a hero, and he had not been one before,” Jim Dowd, then NBC’s publicity director, told Kranish and Fisher.