Urged by a Sadistic Editor, a "New Times" Reporter Skates 26.2 Miles for Ten Grand

Paul Kent looks like a madman. It's 7:30 a.m. on a Saturday, and the world's number-one longboarder is dressed like a cross between a crack-addled aerobics instructor and the Unabomber: shirtless, tiny red shorts, black leggings, futuristic running shoes, shaggy brown hair under a black helmet, sunglasses, and — the coup de grace — a bizarre mustache made up of three triangles drawn with permanent marker. I introduce myself.

"What's up, man," Kent ventures, warming up by swinging his leg back and forth like a scythe through the chilly morning air. "You look like you're in pretty good shape. You'll finish." And with that, he takes off sprinting through the parking lot. He must be in the zone, I tell myself.

Welcome to the Adrenalina Skateboard Marathon: 26.2 miles around the entirely unremarkable suburban streets of Hallandale Beach for a $10,000 check. Kent is one of the favorites to win. Last year, he skated more than 250 miles in 24 hours. That's the distance from Miami to Orlando. On a skateboard. In one day.

As for me, I spent the previous day trying to stay on my friend Victor's longboard. It's been ten years since I was on a skate deck, and I've never ridden a longboard before. When I do, I weave back and forth like a drunk before crashing onto the pavement.

I'll be lucky to finish, but Kent has some serious competition. The prize — roughly $9,000 more than any skate marathon has ever offered — has drawn 125 racers from around the world to the fancy Village at Gulfstream Park mall. But it's about more than the money. The race is also the athletic equivalent of longboarding's quinceañera. After more than 50 years as the stoner's preferred mode of transportation, longboarding as a sport is coming out of its haze. The internet has reinvented the lonely longboard, transforming it from solitary pastime into a cult movement. On a handful of websites, longboarders share videos of flash-mob marathons, cross-country skate trips, and gnarly, high-velocity wipeouts.

"We Will Rock You" blares from loudspeakers as racers strap on skate helmets and kneepads. A purple helicopter buzzes overhead. In my borrowed bicycle helmet and an old soccer jersey, I am clearly not prepared. This is not going to be as easy as I thought.

Mile 0: We line up like cattle between two metal gates. There are 18-year-old Matt Elver, a watery-eyed Brit university student who holds the world record in the marathon at 1:43; and Rudford Hamon, a Miami perfume entrepreneur and tae kwon do champion who's been training for six months for the marathon in the hopes of putting the ten grand toward his upcoming honeymoon. And there's a boisterous group of New Yorkers in dreadlocks, tattoos, and skinny jeans that drove 20 hours in a minivan to get here. Among them is Jeff Vyain, a former college cross-country star.

Just before the start, I take stock of my position in the pack. I am sandwiched between a septuagenarian with a pole to help him push and a 12-year-old whose father will not stop taking photos. I change my goal from simply finishing the race to kicking this duo's ass.

By the time I get to the Gulfstream parking lot, Kent, Elver, and the New Yorkers are already disappearing ahead of me. I can barely make out Hamon, who in his yellow helmet with a camera looks like a Teletubby, pushing heartily against the wind.

Mile 2: The people of Hallandale stumble like zombies onto their front lawns, clenching mugs of coffee or newspapers. Most pause when they see the parade of testosterone skating by. "What the hell," one woman mutters. Police officers stop traffic for us at every intersection.

So far, so good. My legs feel strong, and I quickly reach a comfortable 10 mph. I have left the 12-year-old behind and settle at the heels of a stocky teenager with blond curls, a bandanna, and purple shoes. The rest of the long procession fades from view, and Bandanna Boy quickly becomes the bane of my existence. When I move left, he moves left. When I move right, he moves right. And when I try to pass him going up a hill, my shoe catches my wheel. I screech to a stop in my sneakers as my board shoots off the road. I hear Bandanna Boy snicker in the distance.

Mile 6: After one lap around utterly vanilla Hallandale, we ride back to Gulfstream. Our wheels click over the faux-cobbled streets. The race leaders begin streaming past us, already on their second lap. Kent, Vyain, and Elver are all up there. Hamon is laboring, five minutes behind.

By my second lap, I have learned to switch my pushing foot every couple of minutes: This revelation is like discovering the internal combustion engine. Soon I scoot past Bandanna Boy. Despite my four hours of sleep and inexperience at skateboarding, I'm feeling great.

But the warning signs are everywhere. The streets of Hallandale run purple with Vitamin Water-enriched puke. I've passed a dozen skaters who've dropped out due to cramps, pulled muscles, or sickness. The atmosphere is more NASCAR than SoCal. And when a skater blows a bearing in front of me, men on scooters zip over and whisk him back to the starting line for repairs.

Mile 15: Consider the longboard: a thin, three-foot-long plank of wood attached to four wheels. But its simplicity is beguiling. The angle at which your foot hits the ground is unnatural and, over a long distance, dangerous. By the end of Kent's 250-mile, 24-hour ultraskate, he had wrecked the bones in his left foot. "The race really became about just enduring excruciating pain," he says. "You grit your teeth and bear it, but it lasted for another five hours." Kent's time in the Canadian Army taught him how to endure pain and discomfort, even when "your mind is questioning everything, trying to get you to stop."

I didn't even know there was a Canadian Army, and the extent of my mental training is withstanding my editor's endless abuse. So when I'm halfway through my third lap and my calves feel like they are pulling away from my tibias, I begin to wonder, Why the fuck am I doing this?

Mile 18: "Hey... dude... This your... third lap?" I wheeze to the six-foot-four skater next to me.

Andrew Lightfoot looks like I feel: sick. He's one of the few racers from the West Coast to fly all the way here. He skated 500 miles down the Cali coast this summer, but today he's been throwing up at least once per lap. The fact that he's anywhere near me is not a good sign for the veteran skater. Then he pushes on ahead, leaving me alone again.

Mile 20: By my fourth and final lap, each push sends streaks of lightning up my legs. But as I'm about to leave Gulfstream and head back onto the streets of Hallandale, a volunteer in a bright orange vest shouts, "If this is your last lap, stay left!"

Twenty miles on a skateboard in the South Florida sun will do strange things to your brain. I gleefully follow the volunteer's advice, only to find myself back at the starting line. Trying not to stop, I ask several other volunteers how many laps we're supposed to do, but they just shrug. Somehow, on a closed circuit, I am lost.

The announcer shouts that Vyain is about to cross the finish line, so I do another lap around the starting area to watch the finish. He cruises in at 1:40:58, a new world record. "Now I can get LASIK surgery," he pants.

"Yeah, you're blind as fuck," his friend Billy Cole adds with a high-five.

Elver finishes six minutes later, in seventh place. Kent rounds out the top ten. When I find Hamon, he looks like he's aged 30 years — sweat is caked on his skin. "Those guys are monsters," he says, stunned.

The day after: Sunday morning, I step out of bed to make coffee, but my calves — balled into knots — do not cooperate. I slump to the bedroom floor. So this is what it feels like to be old. I slowly crawl to my computer to confirm the inevitable: I have been disqualified from the marathon.

Then again, so were 54 of my fellow racers. At 44 percent, that's a lot worse than the 2 percent who drop out of the New York Marathon. Ah, sweet schadenfreude. Finally comfortable with my abject failure at longboarding, I take some ibuprofen and go back to bed.

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Michael E. Miller