Image via Sam Woolley

Racing is full of wealthy weirdos, but a good many of them are well-pedigreed offspring out to blow the last of their family’s money in an attempt to stave off boredom. That wasn’t Preston Henn, who used his self-made fortune to win the 24 Hours of Daytona—twice. Henn died Sunday at 86, and leaves behind one of American racing’s more interesting legacies.

Henn was probably racing’s most successful “Florida Man.” The eccentric businessman turned a drive-in theater/flea market into a multimillion-dollar fortune, which in turn funded a racing program.

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While it’s not uncommon to see racers’ own businesses on cars, Henn’s Swap Shop was of a different breed than the usual fare you’d see at a race. His Porsche advertised his own Florida chain of flea markets alongside luxury brands like Rolex and Martini—just in case you needed to find a knock-off Rolex after the race.

Henn reportedly died of natural causes. It’s unlikely modern racing—clean, manufactured and brand-friendly as it is—will produce another racer quite like him.

The Disneyland Of Flea Markets

Henn’s empire started with a drive-in theater in Franklin, North Carolina, taht Henn leased with a $4,000 loan from his father. It was the only evening entertainment for miles, and became successful enough that Henn started buying other drive-ins.

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Henn opened the original Thunderbird Swap Shop in Fort Lauderdale in 1963 as a drive-in movie theater, but quickly decided that its nine acres of land was the ideal place to hold a flea market.

Kevin Jeannette, who was the crew chief for Henn’s 1983 Daytona-winning team, explained to Racer that Henn got the idea to hold a flea market during the day at the Thunderbird drive-in from a trip to California:

He was on the freeway in Compton, saw a drive-in movie theater that had a sign that read “swap meet Saturday and Sunday,” and he stopped in and couldn’t believe what he saw. [...] He liked the idea that they could make money during the day on this big drive-in property by charging people to come in and sell their stuff, and then they cleared out and he showed drive-in movies at night.

By 1985, the Thunderbird Swap Shop had grown to over thirty acres, with more expansion on the way, in no small part thanks to Henn’s penchant for self-promotion.

“This one makes more money than all the others combined,” Henn told the South Florida Sun Sentinel in 1985. “My goal is to make it the Disney World of flea markets.”

To wit:

If Preston Henn thought a garish advertisement on his necktie would bring just one more person to his Thunderbird Swap Shop in Fort Lauderdale he would:

1) begin wearing a necktie immediately and

2) advertise on it.

What better hobby for Henn to take up than motor racing, then? Not only does Florida embrace the sport like nowhere else, but the vehicles themselves are rolling billboards.

Cars on display in the Swap Shop. Screencap via Sun Sentinel.

Billboards With Engines

Henn started racing boats just like his father, winning the Bacardi Trophy Offshore Powerboat Race twice. He moved into cars after a bad offshore racing crash left him stranded in the late 1970s.

Jeannette described the incident to Racer:

In one race off the coast, he crashed and the only thing that saved him was a helicopter came by and saw him bobbing up and down in the water. After that, he said enough with the water; I’m racing on land.

According to Ultimate Racing History, Preston Henn first dipped his toes into the world of professional auto racing with Spirit Racing’s Porsche 914-6 at Sebring in 1977, only to follow it up with a Swap Shop sponsored entry at the Daytona Finale 250 Miles in a Ferrari 365 GTB/4. From there, Henn started racing in the IMSA GT championship and Trans Am, both in his own cars as well as on other teams.

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Race cars also fit Henn’s need to sell, sell, sell. To a man who often wore t-shirts urging people to visit his Swap Shop, cars were far more visible. Henn even put his collection of exotic and race cars on display in the middle of the Swap Shop to bring in more traffic.

Like many endurance racers in the late 1970s, merely finishing was a feat that eluded Henn for several years. Henn even enlisted the co-driving abilities of Brumos Porsche owner and Trans-Am star Peter Gregg and legendary Porsche racer Hurley Haywood for the 1979 12 Hours of Sebring only to have engine woes drop them down to a 26th place finish, according to Racing Sports Cars.

Henn’s first finish as a driver wasn’t until April 8, 1979, in a Thunderbird Swap Shop Porsche 935 at Road Atlanta, racing in the IMSA GT Championship. He finished nineteenth in the relatively short 100-mile race, but it was a start.

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Henn also took his first trip to the 24 Hours of Le Mans in 1979 with the famous North American Racing Team in a Ferrari 512 BB/LM, but the Ferrari crashed out on lap 54.

Photo credit: AP Images

From there, Henn took the Swap Shop Racing team worldwide, competing in more FIA World Sports Car Championship events in 1980. The WSCC, which is essentially the granddaddy of the World Endurance Championship we know today, took Henn to the Nürburgring, Silverstone, and of course, back to Le Mans. It was then that he added a cowboy hat to his personal look.

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“It was my symbol overseas. They called me Le Cowboy Preston,” Henn told the Sun Sentinel. “It makes it easy for people to recognize me. […] If you don’t get recognized, you’re nowhere.”

“Who The Hell Is A.J. Foyt?”

Of all the legendary names Henn raced with, Henn may be best known for racing with A.J. “Super Tex” Foyt. Foyt became the only driver to win the Indianapolis 500, the 24 Hours of Daytona, the Daytona 500 and the 24 Hours of Le Mans, and Foyt got his first 24 Hours of Daytona win because of Henn.

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In 1983, Henn asked Foyt to codrive a Porsche 935L with himself, Bob Wollek and Claude Ballot-Léna. Foyt, who had originally signed up to race a different car that had broken at the race, wasn’t exactly familiar with the 935L when he was asked to drive it. Kevin Jeannette recounted Foyt’s first experience with Henn’s T-Bird Swap Shop 935L to Daytona International Speedway:

Just prior to getting in, Foyt asked me about the car. I told him it drove just like a Porsche, only faster. A.J. asked me about the shift pattern and I told him it was an H pattern, just like a Volkswagen. He looked at me and said, “You think I’ve driven a Volkswagen before?” We had a laugh and I told him the pattern.

Frenchman Wollek wasn’t as familiar with Foyt’s racing cred as the rest of the team. When he came up at 5 a.m. to see the rest of his team standing in the pits, they told him told Foyt was driving. “Who the hell is A.J. Foyt?” he asked.

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When Foyt returned after a four-hour, ten-minute stint, Foyt had laid down the fastest lap of the race and had increased the team’s lead from one to two laps. Now impressed, Wollek finished off the race for the win.

Photo credit: AP Images

Porsche After Porsche

Henn continued to campaign the mighty Porsche 935 through the mid-1980s, but the new hotness was soon the Porsche 956, a Group C car truly worthy of the World Sports Car Championship. The Porsche 956 gave Henn his only finish at the 24 Hours of Le Mans in 1983, finishing tenth overall.

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When Porsche came out with the 962, Henn started racing one too, per Racing Sports Cars. While ignition problems struck Henn’s 962 in its 1984 debut at Le Mans, it went on to win the 24 Hours of Daytona outright in 1985.

Henn’s 962, driven by A.J. Foyt, Bob Wollek, Al Unser Sr. and Thierry Boutsen, beat the almost-factory Lowenbrau Porsche 962 to win Daytona in the last hour, despite the fact that Wollek and Foyt were both sick with the flu. (Racer’s account of this insane, sniffle-ridden win is a solid read in its own right.)

Foyt and Wollek, who had now become friends, took Henn’s 962 to win the 1985 12 Hours of Sebring, per IMSA.

Photo credit: AP Images

The Wrath Of Henn

While Henn’s teams were successful, you didn’t want to encounter his angry side. “People think A.J. [Foyt] has a temper, but he never threw a helmet at me ... but Preston did!” Jeanette told Racer.

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When a spat between 1986 Grand Prix of Miami race promoter Ralph Sanchez and Henn almost prevented reigning Indianapolis 500 winner Danny Sullivan from racing with the Henn team, Sanchez got the full brunt of Henn’s wrath, according to the Sun Sentinel.

“Believe me, nobody has ever treated me like that,” Sanchez told the Sun Sentinel of the conversation he had with Henn in the race pits. He repeatedly was cursing at me. We had a deal already set. I was very angry after that.”

While he certainly had a temper if you crossed him the wrong way, those who knew him described him as an exceedingly caring man—so long as he trusted you.

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“If he knew you were there for the right reasons, and many weren’t, he was the most generous person in the world,” Jeannette told Racer. “He became like a second father to me.”

Easing Into Old, Stubborn Age

Henn’s Swap Shop Porsche 962 raced once more at the 12 Hours of Sebring, but he inexplicably ceased all racing activities shortly afterwards. All of that, mind you—the triumphant Porsches, the drives in Ferraris and top-level talent—was funded largely by Henn’s humble flea market empire.

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Meanwhile, the Swap Shop flea market continued to grow, as did his car collection housed there.

Henn even received permission to keep his Ferrari FXX—most of the 30 in existence are kept by Ferrari—with the rest of his collection, complete with “Swap Shops” decals on the side. The collection is valued at upwards of $100 million, per the Miami Herald. (And of course, while he loved Ferrari, he was also famous for suing them. Henn filed a lawsuit against the automaker last summer because it refused to sell him a LaFerrari Aperta, a suit he later dropped.)

Despite seeking international notoriety for the Swap Shop, the only Florida Man stories you’ll hear are from the Swap Shop and his racing team, not his expansive home. Henn explained his desire to keep his personal life personal to the Sun Sentinel:

I come up here [to my home] and lock myself up. Up here people can’t find me. I can go through the office with phone calls. I am happy by myself and enjoy my quiet periods here. Betty and I don’t entertain — we don`t enjoy formal parties. And, we don’t know our neighbors. We don’t really know anyone in the area. I don’t have many friends. A lot of people call me a recluse but I am not. It`s that when I come home I don’t come here to socialize. I come here to pursue what I am currently interested in. There are so many things I know I will never be able to get to in my lifetime.

Just because he wanted to stay out of the public eye didn’t mean he was successful. According to local news reports in the Sun Sentinel, he spun animal rights protests over the Swap Shop’s on-site circus as free publicity and painted entrance signs fluorescent orange to annoy local aesthetic tastes and delay annexation of the Swap Shop’s former Delray location, among other things. (The Hanneford Family Circus at the Swap Shop was fired by Swap Shop and replaced by more space for Henn’s car collection in 2005.)

And in proof that you can’t take the Florida out of the Man, Henn was arrested in 2005 and charged with two counts of battery of a law enforcement officer, simple battery and criminal mischief over a fight he got into with a Broward County sheriff’s deputy. Henn was trying to evict a longtime vendor when sheriffs were called to mediate the dispute, per the Sun Sentinel. Then Henn locked himself in his office, reportedly pushed someone when he finally came out.

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The sheriff’s deputy ultimately subdued Henn with a taser before taking Henn into custody for a psychiatric evaluation. According to The Neil Rogers Show, Henn not only threatened lawsuits after the arrest, but he also challenged Broward Sheriff Ken Jenne to “an old-fashioned fist fight.”

The misdemeanor battery charge was later dropped, and Henn even apologized to the Sheriff’s Office over the incident, reports the Sun Sentinel.

However, he mocked the ordeal in a series of ads for the Swap Shop, proclaiming that deputies “tasered me because I was wild about the prices.”

Still Flashing That Cash Into His Final Years

Henn never retired from the Swap Shop, as he still liked to don a cowboy hat and patrol the grounds in a golf cart—nor did he tone down his flashy tastes.

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He described a 2013 $5.5 million settlement with Coach over counterfeit bags at the Swap Shop as “pocket change” to the Sun Sentinel and had just become the first buyer for the Gulfstream G650, a $71.5 million jet that was capable of speeds just below the speed of sound.

You can’t keep an old racing driver from going fast. Despite being through with racing, he also still liked to take his Ferraris and other exotics out on track.

“He wanted to go 180 [miles an hour] on the straightway on his eightieth birthday,” Henn’s lawyer Bob Scherer told the Sun Sentinel of one outing in a half-million dollar Ferrari. “The straightway isn’t that long. And damned if he didn’t do it.”

Photo credit: AP Images

Should you want to follow in his eccentric steps, Henn offered this advice to young entrepreneurs in 1985, as quoted in the Sun Sentinel:

Keep mentally active. So many people have good brains but they don’t try. It all boils down to how you apply yourself. Acquiring real estate is still the big secret of all of it. That and advertising. Remember that even though you are starting in your 20s or 30s, you don’t have all that much time to do what you want to do. For many years your work will take all your time and all money made must be put back into the business.

This is hard to take but must be faced. I was in my 40s before I was able to spend my money.

Of course. Advertise, advertise, advertise. It worked for Preston Henn.