See Donald Trump Morph From Man to Cartoon

In the 2004 series premiere of The Apprentice, the reality competition show that laundered Donald Trump’s reputation as a tacky sleazebag and launched his presidential aspirations, the billionaire real estate mogul reintroduces himself to America with a glossy, vague little anecdote about overcoming financial adversity. In a preamble to the show, he narrates over sweeping aerial shots of New York City — “my city,” he calls it — and footage of him flying over his own shiny buildings in his Trump-branded helicopter. “It wasn’t always so easy,” he says. “About 13 years ago, I was seriously in trouble. I was billions of dollars in debt. But I fought back and I won, bigly. I used my brain, I used my negotiating skills, and it worked it all out.” 

In reality, Trump had climbed out of that $3-plus billion debt in the early 1990s reportedly by taking out loans from his wealthy father and siblings and evading federal taxes. But he doesn’t get into those details; instead, he moves right into introducing the 16 twentysomething Ivy League grads and entrepreneurs who will be competing each week for a chance to “work for the Donald” and potentially, maybe, become a billionaire themselves.

Cut to the first morning of competition. The gaggle of young, conventionally attractive contestants gathers in the New York Stock Exchange and gazes up adoringly at Trump, who addresses them from a high royal balcony. He’s 20 years younger than we see him now — his hair darker and fuller, his makeup less cartoonishly orange, his demeanor more reasonable and even charming. “This is really and truly the center of the world for big business,” he bellows down at his apprentices like some kind of benevolent finance deity. And then he separates the men from the women and shoos them out into the streets of Manhattan to compete at selling lemonade. 

WHEN TRUMP FIRST THREW his hat into the Republican presidential primary in 2015, I was a young politics reporter at the Huffington Post. And I remember us all thinking at first that his candidacy was some kind of joke or reality TV bit — to such an extent that our editorial director and Washington bureau chief issued a joint statement in July of that year announcing that we had decided to cover Trump’s campaign in our Entertainment section, rather than in Politics with the other candidates. “Our reason is simple,” they wrote. “Trump’s campaign is a sideshow. We won’t take the bait. If you are interested in what The Donald has to say, you’ll find it next to our stories on the Kardashians and The Bachelorette.” 

We took a lot of flack for that decision, obviously, and came to regret it as it became clearer by the week that a whole lot of voters were dead serious about electing Trump. Five months later, Arianna Huffington announced in a new statement headlined “We Are No Longer Entertained” that we would be covering him as a politician going forward. What we had failed to appreciate at the time was the extent to which Trump’s hit reality show and the “business genius” persona it created had essentially propagandized tens of millions of viewers into believing he was the only man strong and savvy enough to solve the nation’s problems and deliver them the American dream. Producer Bill Pruitt later admitted that this was by design — that show creators “played fast and loose with the facts” and “conned” us all about our future president. “By carefully misleading viewers about Trump — his wealth, his stature, his character, and his intent — the competition reality show set about an American fraud that would balloon beyond its creators’ wildest imaginations,” Pruitt wrote for Slate last year.

“Our job was to make him look legitimate, to make it look like there was something behind it, even though we pretty much all knew that there wasn’t,” producer Jonathon Braun, who’d also worked on Survivor, told The New York Times a few months later. And it worked: While the most recent Gallup poll before The Apprentice aired found that 58 percent of people had an unfavorable opinion of Trump, half of Americans had a favorable view of him in the same survey 18 months later. 

That fraud has ballooned now, of course, into a second presidential term for Trump. In a full-circle moment, tech billionaires are now openly competing and humiliating themselves for Trump’s favor the way his 25-year-old Apprentice cast members did in his fake boardroom in the mid-aughts. Amazon owner Jeff Bezos, to that end, bought The Washington Post and turned its opinion pages into a conservative echo chamber. And Amazon Prime Video announced earlier this month that it would be streaming the first seven seasons of The Apprentice for the first time, kicking royalties back to Trump, who not only starred in but was a producer of the show. (Amazon has also paid $40 million for a vanity documentary about Trump’s wife Melania that no one asked for.) 

For someone such as myself who had never watched The Apprentice during its original run (and even for some who had), its arrival to streaming presented a terrible but useful opportunity: to examine at close range the cultural moment that made Trump a viable public leader, and the person he showed himself to be. I lasted through the first three seasons.

WHAT’S MOST JARRING, straight away, is how utterly different Trump is as a man on this show from the villainous buffoon we now see in the news. He comes off as savvy, fair, and even empathetic. In Episode Seven, he pulls one of the contestants aside after a board meeting to ask her about her ailing mother’s health and offer what appears to be genuine support and concern. “I felt like I was talking to a friend as opposed to talking to this mogul billionaire,” she gushes after the conversation. 

He has genuinely funny banter with the contestants, and they actually seem to enjoy being around him, even when he’s deciding which one of them to fire. In one such boardroom meeting at the end of Episode Six, Trump asks Omarosa Manigault, who’s framed as the villain of the season, how she thinks her teammate Heidi did in that day’s challenge. “Heidi was fantastic!” Omarosa responds with a big smile. “And I will tell you that I haven’t always been the biggest fan of Heidi. I haven’t always thought that she was professional, nor does she have much class or finesse…” 

“That was very nice,” Trump interjects sarcastically, making the whole room laugh, including Heidi and Omarosa and his two advisors. “This is one of the worst compliments I’ve ever heard.” 

In Season Two, a cast member named Ivana has Trump making ex-wife jokes throughout the first few episodes. “Ivana, ay-yi-yi,” he intones upon hearing her mentioned in the boardroom in Episode Two, getting big laughs again. “Every time I hear that name.” 

Trump also makes some unexpected decisions about whom to fire each episode that do make him seem pretty sharp and insightful, zigging when you think he’s going to zag. When the whole team gangs up on one person to try to get them fired, as with eccentric Sam in Season One and restaurateur Stacie in Season Two, Trump sees right through the plot and shuts it down. In Stacie’s case, every person in the boardroom, including one of Trump’s henchmen-advisers, recommended that she be fired after an ice cream challenge in which she stood on the wrong block the whole time. The second obvious option to be fired was Ivana, the team leader who everyone agreed was indecisive and disorganized. In a shock decision, Trump went his own way and fired Bradford, the best performing member of the team, because Trump said he’d made a “stupid, impulsive, life-threatening decision” by waiving the immunity he’d won in the previous challenge in a show of self-confidence. Bradford thought Trump would respect his self-confidence; Trump instead was just mind-blown by a man putting his job on the line for no reason. (Producers later admitted that some of Trump’s decisions came so out of left field — sometimes presumably being the only cast member’s name Trump could remember in a particular moment — that they had to go back and comb through the footage to make whomever he fired look bad in the episode.) 

OF COURSE, GLIMPSES of the Trump we know shine through in little ways. He makes a show of loathing interpersonal “disloyalty” and “weakness” among the candidates more than anything having to do with business acumen. After the exchange he has with Heidi and Omarosa in Episode Six, for instance, he lights into Jessie, another teammate that Omarosa had insulted in the boardroom, for failing to punch back. “I hated the way you took so much crap from Omarosa,” he tells Jessie, adding that he found it “repulsive” how she let herself be treated “like a dog…To me that was a form of weakness.” He fires Jessie instead of Omarosa for that reason, despite Omarosa being a rude bully right in front of him, the leader of the losing team, and the obvious choice to send home. 

Trump also uses the show — whose opening theme song is “Money” by the O’Jays — to cast himself as both the embodiment and the arbiter of the American dream, convincing these wide-eyed hopefuls that his billionaire “lifestyle” is actually within reach for them and for anyone who masters negotiating like he did. (At the same time, he tells them in the first season that negotiating “is not really learned. It’s in the genes. A negotiator is born.” He’s half-right, if “in the genes” means starting out with a half-a-billion-dollar inheritance from your dad.)

He brings them to the Wollman Ice Skating Rink in the middle of Central Park midway through Season One, in one of these displays of prowess, and claims that his business genius is the only reason it’s there. “It’s one of the things that frankly I’m the most proud of,” he says. “The city spent seven years and 21 million dollars and couldn’t get an ice skating rink built. I got tired of watching and went to the mayor and said, ‘I wanna build the rink.’ I got it built in three months for less than 20 million dollars.” In reality, Trump convinced a construction company to do the job at cost in return for the promise of massive publicity, and then he refused to mention them at all after they finished it.

And after flexing his big dealmaking muscles for the contestants each episode, he sends the winning team either to drool (or pretend to drool) over one of his personal properties or experience a taste of his obscenely wealthy lifestyle. The first group of winners, the all-women team who made more money than the men peddling lemonade (by recognizing that “sex sells,” Trump observes), are rewarded with a private tour of Trump’s Manhattan penthouse — a gaudy marble and gold eyesore that looks like the entrance to a Russian oligarch’s private spa. “This is like…..rich,” one cast member tells the camera of Trump’s apartment, apparently coming up empty on other adjectives. 

The Episode Two reward is a private jet trip to Boston, which a young blonde named Kristi describes as a “teaching tool.” “You have to want those things and aspire to those things if you wanna be like Trump,” she explains. 

Later in the season, Trump sends the winning team to Seven Springs, his opulent, 230-acre private estate that span three towns in tony Westchester County, for “the best picnic you’ve ever had” in “the most beautiful house in New York State.” It’s certainly not; the place has zero character and comes off as cold and severe. But the players have to sit on a blanket on this comically large, flowerless lawn and pretend like this awkward picnic is some kind of orgasmic bacchanalian feast.

That, if anything, is the throughline in The Apprentice — every single cast member, including two of Trump’s real-life advisors, Carolyn Kepcher and George Ross, kissing his ass and treating him like royalty. In Season Two, Trump enters rooms to literal fanfare. The women on the show, in particular, always seem to gaze at him with little hearts for pupils. 

It’s no wonder that after 14 seasons of The Apprentice Trump expected to be treated like a king when he entered the Oval Office. But the stakes are so much higher now. There are still sycophants and acolytes, but no savvy producers to make his head-scratching moves appear to make sense. Instead of fake-firing fake employees from a fake boardroom, he is firing thousands of real government workers. Instead of making arbitrary decisions about the futures of a handful of fame-thirsty reality stars, he’s making them about immigrant families who came to America for a better life. Instead of blustering about his business savvy from a soundstage, he’s doing it from the presidential podium, using tactics that nearly every economist has warned against to move the United States into an economic “Golden Age” that’s shaping up to look more like a recession.

None of this should be a surprise, really. After all, just two seasons into The Apprentice, Trump no longer felt the need to introduce himself to America with an anecdote about personal struggle. “My name is Donald Trump,” he says in the Trump helicopter over Manhattan in the Season Three premiere. “You know everything about me.”