Campaigners waving signs in Altamonte Springs, Florida, including Burma Davis Posey (far right)
Campaigners waving signs in Altamonte Springs, Florida, including Burma Davis Posey (far right) © Michelle Bruzzese

It is late September, the morning after the first presidential debate, and the reviews for Donald Trump’s performance are grim. The betting markets, pollsters and most pundits have pronounced Hillary Clinton the winner. “Trump choked”, declares William Kristol, editor of the conservative Weekly Standard.

Yet Randy Ross is a man in high spirits as he bounds into the Trump campaign’s downtown Orlando office. He watched the debate with other supporters, sipping white wine at a local bar. Despite the negative reaction elsewhere, Ross deems Trump’s performance “amazing”. “Hey! We’ve got the same shirt on!” he calls to a fellow volunteer, pointing at their matching Trump-Pence white T-shirts. “Yes we do, yes we do!” he sings.

In his previous lives Ross has worked at nearby Disney World, produced exercise videos for children, and run unsuccessfully for office (school board, city council and mayor). Now he has found himself as Trump’s campaign chairman for Orange County, the fifth-largest county in Florida and one of the few swaths of the country that decides presidential elections.

Today, he is on his way to meet Trump at a Florida fundraiser, and is late to our meeting because he’s been busy getting a spray tan, so as not to be out-oranged by Trump in the event photographs. By noon, he has already downed something called a Monster drink, the beverage he relies on to get him through long days ferrying Trump yard signs and papers between the campaign’s various field offices. “I need Botox right now,” he groans. “The stress, you know?”

Ross, is not a typical Republican campaign chairman. For one, he is an ex-Democrat; for another he is gay. In his pre-Trump days, he donated money to Hillary Clinton’s 2008 primary campaign and went on to support Barack Obama after Clinton dropped out. But by 2012, he found himself drifting away from Obama. He was frustrated that the Democrats seemed to spend all their time talking about social issues, and not enough time fixing what he believed were the country’s real problems: a stagnant economy, misguided foreign policy and rampant illegal immigration.

Randy Ross, Trump’s campaign chairman for Orange County
Randy Ross, Trump’s campaign chairman for Orange County © Michelle Bruzzese

The moment he realised he was a Trump supporter, he says, was the night of the first Republican primary debate, in August 2015. There were 17 Republican primary candidates in the field, and already Trump appeared to be swallowing all the oxygen in the room, something Ross found more than a little appealing. “You know, I want someone who’s going to make me stand up and clap. And I remember actually clapping for him. I was like: ‘Oh my God!’”

He began making phone calls, trying to get on board the campaign. For weeks, they went unanswered. Then he discovered why. Five months into Trump’s presidential bid, the candidate had no campaign operation in this important city. After weeks of pestering Ross was anointed chairman for Orange County.

Trump supporters at Trump / Pence rally, Ocala, Florida, October 12, 2016 credit Michelle Bruzzeze
Trump supporters at Trump-Pence rally, Ocala, Florida in October © Michelle Bruzzeze

His star has risen dramatically. By August, he was one of those introducing Trump at a Florida rally of more than 8,000 people. “Here’s my message,” an elated Ross told the crowd. “I’m a 50-year-old man who is a Republican that happens to be gay, who is an American. And I will not go back in the closet because I am supporting Donald J Trump for president!” he roared to cheers. “It’s about time we have a president that inspires us and reminds us what it feels like to win!”

Ross says the campaign asked to see a copy of his speech beforehand. “They didn’t change one thing,” he beams.

During the past 15 months, a variety of theories have been advanced to explain Trump’s rise: the economic decline of white, working-class families; a desire to shake-up a dysfunctional system; a racist backlash against eight years of a black president.

Yet in some corners, support for Trump confounds traditional identity politics and has more to do with an emotional attraction to his candidacy. For these supporters, even his gaffes are seen as strengths and further proof that Trump is closer to the average American than he is to the country’s political establishment. The latest controversies — a string of allegations from women who allege that Trump forcibly groped them, in one case “like an octopus” — have only added to the prevailing wisdom among his diehard supporters that the political and media elite is doing everything in its power to prevent a Trump presidency.

What do they like about Trump? All the things they believe the mainstream politicians and media does not. Trump, like them, has made mistakes. Trump, like them, has had financial difficulties, but managed to overcome them, making his fortune back and cleverly exploiting the loopholes of the American tax code in the process. They like his celebrity.

Beverly Burgess pictured at home in Pine Hills, Orlando © Michelle Bruzzese

It is Trump’s failures, his riches-to-rags-to-riches story, that holds particular appeal in Orlando, America’s Disneyfied ode to make-believe. For those still reeling from the 2008 housing crash, or just trying to get back to brighter days. Trump offers hope, even now. That, with fewer than three weeks to go until election day, he will pull it all off again, defying the naysayers who stopped believing in him.

As Ross puts it. “We all like a comeback. Second chances, third chances. I don’t care how many chances. I think in the end we all want another chance.”

While the field offices of Clinton’s Florida campaign tend to be staffed by digital-savvy millennials who have descended into the swing state armed with briefings from Clinton HQ in Brooklyn, Trump’s volunteers here are of a different stripe. There is a former New York City Rockette who mans the phones, and a one-time Miss America contestant provides the musical entertainment. Their ranks are rounded out by a woman who pulled herself out of homelessness to become a high-flying Florida real estate agent and two high-school students, including one of British origin who likes Trump because he reminds him of Margaret Thatcher.

Carolyn Bourland, a volunteer at the Trump call centre in Orlando © Michelle Bruzzese

On one of my early visits in mid-September Ross, who likes to adorn the drab HQ with decorative flourishes he calls “Randy bombs”, had been to a craft store, where he’d bought gold spray paint and a bejewelled American flag with which to bedazzle one of the black office phones — a prize, he explained, for the Orlando office that managed to make the most weekly phone calls.

At a phone-banking party a few weeks later, though, the mood is pandemonium. On TV, Fox News anchors are discussing whether Trump still has a shot at the presidency following sexual assault allegations. Inside the room, more than two-dozen volunteers have sat down in three neat rows to make calls, but Ross can’t get the phones to work despite many attempts to reboot the system. The only thing working in the room is a call bell on one of the desks, which one volunteer is repeatedly hitting with gusto.

“Oh God, make the phones work,” Ross pleads. He turns to one of the group’s more religious volunteers. “Are you going to pray some more for the phones?” he begs. “Please?”

Ross grew up in an evangelical, Republican household in Indiana. He moved to Orlando to work at Disney World, 30 years ago, and a few years later returned for good. There were setbacks: the failed runs for office; a failed audition for Trump’s reality TV show, The Apprentice. (“I didn’t make it out of the room.”) In 2015, Ross pleaded guilty to insurance fraud for falsely claiming that $35,000 worth of lawn furniture had been stolen from his Orlando home, an incident he prefers not to talk about. But he is not the only campaigner in the office who believes Trump can bring them a second chance. At one of the weekly phone-bank parties, I meet Beverly Burgess, a 53-year-old African-American who, after 34 years voting Democrat, has recently come around to supporting Trump, much to the delight of his other supporters.

A volunteer at the Trump call centre in Orlando © Michelle Bruzzese

“At first I wasn’t too supportive of what Donald Trump was saying,” Burgess starts to say.

“That’s because you didn’t really know what he was saying,” a white Trump supporter interjects.

Burgess pauses, then continues: “The more Trump spoke the more he made sense. From a business standpoint he’s had it; lost it; had it; lost it; and had it again. And, to me, in America we have to get back to taking care of America first, taking care of the small business owners like me first that provide jobs.”

Her new plan is to start her own barbecue restaurant, using a family recipe, but she doesn’t have enough savings. Her disillusionment with the Democratic party, she says, came on the heels of losing her job as a grant writer for the Florida governor’s office 12 years ago.

“Listen, I didn’t leave my job, I lost it. You know what that makes a person feel like?” The barbecue business, she says, is one of the only ways for her to pull herself up. “All I need is someone to take a chance on me.”

Burgess says her support for Trump has alienated her from other members of the black community. Not that she minds. “I’m like Janet Jackson: ‘What have you done for me lately?’ The Democratic party: ‘What have you done for me lately?’ ” she huffs. “I said: ‘You’ve lied, you haven’t kept any promises . . . Now here comes this little man named Trump who wants to make America great again and y’all have got a problem.’ So when my little Democrat friends come at me and say I’ve been hanging around too many white people, I say, ‘You can kiss my black ass.’ ”

The Trump call centre offices in Orange County, Orlando © Michelle Bruzzese

Her friend Burma Davis Posey’s path to supporting Trump has been more straightforward. Davis Posey, 69, is a former Miss Georgia. In the 1968 Miss America pageant, she sang “This Is My Country” and unveiled her painting on stage of a “nine-foot American flag bursting through a thunderhead with an eagle flying up to the flag”.

In her twenties, she became a professional evangelical opera singer, and married a dashing Orlando dentist. “When we walked out the door we were Barbie and Ken,” she says. In reality, he abused her. After 13 years she divorced him and remarried. But in the past few years, there have been a new set of problems. Her second husband’s business dried up during the financial crash. Now they are battling piled-up medical bills and have moved in with Posey’s adult daughter to cut costs.

Posey sympathises with the women who have come forward to accuse former President Bill Clinton of sexual assault. But those feelings do not extend to the women who in recent days have accused Trump of groping, something she believes is a conspiracy to try and take the election away from him. As for the comments Trump made on that video, she says: “Those were his pre-Christian days.”

In the wake of the latest scandal, the us-against-them mentality is only growing. Groups of women that campaign for Trump have been staging sign-waving events at prime Orlando intersections, such as the parking lot for a tropical-themed restaurant called Bahama Breeze. On one recent afternoon, a dozen of them were met with a few disparaging insults, but also honks of approval. One passer-by, a Vietnamese immigrant to the US named Kimberly, comes up to them to ask how she can get involved. “I don’t vote down here,” she says, pointing below her waist. “I vote up here.” She taps her head.

Ross says his support for Trump has meant losing friends, particularly within the gay community. “They don’t understand it. To them, I’m totally strange and odd,” he says.

Toni Campbell, one of the Trump campaign volunteers, tells me her support for Trump has hurt her real estate business and frayed personal ties. “My own dad called me a racist,” she says. Others share stories of Trump signs being stolen from their yards, and cars adorned with Trump bumper stickers being keyed.

Despite it all, spirits remain high. My last meeting with Ross is the night of an Orlando fundraiser. At the start of the day, a fifth woman had come forward to accuse Trump of groping her. A few hours later, oblivious to the looming clouds, 200 Orlando Trump supporters descend on the property of Chris Comins, a local businessman. In the foyer, a life-sized cut-out of Trump stands ready for photos with the guests who have donated a minimum of $250 to attend the event.

Around 8pm, the entertainment portion of the evening begins. Posey sings the “Star-Spangled Banner”From the crowd come chants of “U-S-A! U-S-A!” and “Lock her up!” — a reference to Clinton. Ross hands the microphone to David Siegel, Orlando’s richest man, who has staged his own financial comeback after throwing his money into a 90,000 sq ft Florida replica of the Palace of Versailles. Siegel laughs off Trump’s groping comments. “There are some beautiful women here. I’d like to pat them,” he leers. Besides, he jokes, the recent controversy has at least had one silver lining: the American public can now be sure that Trump is not gay!

A Trump sign outside the Trump-Pence rally, Ocala, Florida © Michelle Bruzzese

Standing next to Siegel on stage, Ross makes a point of laughing. When I ask him about the events of the past week, he lets out a sigh. But he insists that there is nothing Trump could do to lose his support. “Absolutely not. Never. No, no. Nothing.” A video of Trump in a lewd act? A video of Trump using a racial epithet? “I would wonder if we all had some things in our life that we said that we regret,” Ross shoots back.

“I’m confident that on November 8 at 7pm or whenever polls close, we will have done everything we could have done to get this man elected,” Ross says. “And if he doesn’t win, guess what? Four years from now, we try something else.”

Courtney Weaver is the FT’s US political correspondent

Photographs: Michelle Bruzzese

Copyright The Financial Times Limited 2023. All rights reserved.
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