This 'Apprentice' Contestant Loved Trump Until He Actually Became President
Chris Russo in his office. All photos by Jason Bergman


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This 'Apprentice' Contestant Loved Trump Until He Actually Became President

How doubts have begun to creep in for one Trump voter on Long Island.

Chris Russo can boast what most Donald Trump supporters can’t: He’s actually heard the words “you’re fired” in person. For several weeks in 2004, he was a contestant on The Apprentice, at a time when Trump’s power was limited to control over Russo and his competitors in that tense boardroom.

Russo—who made it to the final seven on the show after earning a reputation for his brash, un-PC style—was enamored by Trump’s presence from the beginning. “He would come into a room and everyone’s swarming over him like, ‘Mr. Trump, Mr. Trump, Mr. Trump, Mr. Trump!’” Russo tells me in his sharp Long Island accent.


The 42-year-old pauses his story. The resulting silence feels like a rarity at the office of the investment company he owns and leads in Westbury, New York. For a second, he stares into memory. Then his fast-paced voice rolls on with its normal thunderous excitement. “And he’d have his jacket or something, he’d take his suit jacket and just throw it like, ‘Get the fuck outta here… Someone else pick it up.’

“If he couldn’t find a place to hang his jacket or his coat, he just throws it over to the side, you know? Everyone’s like ‘Ohhh, wow!’ He’s just, he’s a professional, man," Russo goes on. "He’s a professional sales guy. In all aspects, in everything that he does. Always keeps people on their toes. I generally don’t like cocky people. But there’s one thing about Trump that I’ve always liked is that he’s cocky… He’s earned it. He’s earned the opportunity to be a prick.”

But once Trump entered the White House, it became more complicated for Russo to support him. Yes there have been some highs—the economy is one of them, from Russo’s perspective, along with Trump’s “ballsy” stand on tariffs. Then there are those low points—Charlottesville, insane tweets, and the Putin summit—that keep Russo shaking his head and arguing with the Trump supporters he knows.

New York is a blue state but it has strong pockets of red outside Manhattan in its suburbs that often defy the stereotype of “Trump country” as being rural, economically disadvantaged regions. Russo grew up in a basement apartment in West Hempstead, New York, and he now lives in an upper-middle class neighborhood of posh homes in nearby Garden City. “Nearly every single person I know is a Trump supporter,” he says. “Guys that are lawyers, doctors, nearly all my clients. The only ones that probably aren’t for Trump are my black clients, usually Obama guys, and they dislike Trump substantially. Even from West Hempstead everyone I know is a Trump supporter. Guys that are union workers, guys that are pizza guys, all Trump, all Trump. Many are scared to say so publicly because they feel that people will assume they are stupid and racist. I myself wouldn’t walk around with a MAGA hat.”


The suburbs look to be a key battleground in this year’s upcoming midterms, and Russo represents the kind of voter Democrats could theoretically win—fond of Trump, but registered as an independent and with a history of voting for local Democrats. (He says a vote for Hillary Clinton would have been a vote for the mother you do not want.)

These “soft” Trump voters aren’t absolute loyalists. Earlier this month, a CBS News poll found that 68 percent of Republicans approved of Trump's handling of the summit with Russian President Vladimir Putin, while only 29 percent of independents approved. “I was very disappointed by it—extremely disappointed,” Russo tells me of Trump’s press conference with Putin. He now thinks that it’s possible the president was mixed up financially with shady Russians. “I wouldn't be surprised if there's something," he says. "Trump burned all the bridges with the banks in the US in the 90s by either not paying them, burning them, whatever. And I think that he used Russian money from either oligarchs, or their banks, or through LLCs… I’m assuming. I hope not.”

A couple of days after the news conference, Russo showed up at a Starbucks in Westbury where he regularly sits at a table of men who love Trump, a rarity among the patrons. (They were scolded by the manager the day after the 2016 election when one of them bought in a Trump poster and put it on the table, Russo says.) Unlike Russo, his tablemates didn’t much care about the press conference.


"I said, ‘Guys, come on man, come on, you see that thing? Oh, what a fucking disgrace.’ And everyone's like, ‘I don't care, he can do whatever he wants.’ I’m serious. They did not care," he tells me. "They said, ‘They're all fucking criminals, Chris—the left, the right, they're all fucking criminals. He's coming in as a wrecking ball and he's fucking the elites and they just can't stand it.' They're like, 'I support him blind—I don't give a fuck what he does with Putin or with any of this shit. I'm just happy what he does over here—he's got the middle class working again.'”

A newspaper clipping from Russo's office.

I met Russo a few minutes after the market’s opening at his office, where all the televisions are turned to CNBC. Russo spent his first year in the business in the notoriously scrappy scene of Long Island boiler rooms. He quickly exited and spent seven years as a broker before starting his own firm in 2003.

Today, a life-size portrait of Trump stands next to Russo’s desk. There is a Haitian flag pinned on the cardboard lapel, a joking reference to Brian Midi, a Haitian broker who used to work for Russo’s firm and remains one of his best friends. He used to have a picture of the broker next to the flag. “I took a picture and snapped it to him after Trump made the comment about 'shitty little country.' But then I turned (Trump) around so the street could see him. I didn’t wanna see his face no more.”

The conversations Midi and Russo have about race are an intense mixture of shouts of outrage and the occasional locker room joke. “Brian texts me and says, ‘My dream would convert you to be something smarter… like a liberal or something," he says. "And I wrote back to him, 'My dream is to fuck Halle Berry.'”


Russo bursts into laughter. “He says this to me the other day: 'You’re an honorary black man. You and I grew up the same. White people can’t handle adversity. You’re the only white guy I know that can handle adversity.'”

The cutout of Trump in Russo's office

You can’t talk about Trump without considering Barack Obama. And when the conversation goes there, Russo has an unnerving straightforwardness about his rationale for voting against Obama, which makes me check my recorder to make sure it was rolling. “I did not vote for Obama because he was black,” says Russo. “I was not comfortable having a black president… Think about it, all the presidents I ever knew were white. Also, I think my black friends voted for Obama because he’s black. What’s the difference in them wanting the black guy to win and my position. I tell them that too.”

The sentiment was not truly surprising, but his honesty stunned me.

“I’ll say this, as time went on. Obama earned my respect," he adds. "I eventually thought, who am I? Like, who am I that he had to earn my respect? He’s the fuckin’ president. I’m a citizen, right? I guess also more debating with friends and hearing their sides of the story—y’know, what it is to be black or what it is to be from the islands—changed my perspective.”

His perspective on Trump continues to change, depending on the day. “I love the guy. I love the fact that he’s got balls… I hate the shit that he lies about the fact that you’re never going to really know what’s happening with North Korea," he says. "He'll never take a loss and be honest about it. He’d rather lie to try to get the win so that people will believe him. You understand. There’s certain things that I absolutely love and there’s certain things that I don’t. That’s it. I’m divided. I’m divided on the guy.”

Correction: An earlirer version of this piece misstated where Russo was born and how long he worked in "boiler rooms" on Long Island, as well as the year he started his business.

David J. Dent, an author and associate professor at New York University, holds a joint appointment at the Arthur Carter Journalism Institute and in the Department of Social and Cultural Analysis. He is editor of the blog and the author of In Search of Black America . Follow him on Twitter.