Kansas Gambler 500 Teams
photos by Adam Rogan and Matthew Gogerty

The newest motorsport is here, and it’s covered in mud.

It’s 9 in the morning. A hundred people — mostly men in their 30s and 40s, mostly white, mostly bearded and beer-bellied — are standing on a bridge in Fall River State Park, Kansas. A handful are rocking “Make America Great Again” hats, others wear ratty hoodies and American flag t-shirts. Assortments of beers in koozies and heavily caffeinated beverages complete the shivering crowd’s look, many still hungover from the previous night’s festivities. They ache for the open road, to get covered in mud, for the Gambler 500 Rally to start.

But they can’t leave yet. A Gambler 500 isn’t a race, mind you. They have to get instructions first. The weekend-long “navigational challenge” isn’t a test to see who can go the fastest. It’s who can have the most fun, fun derived from the inventiveness of its competitors — decking out their cars in obscene ways, carving their own paths, drinking the nights away. This is how gearheads spend their weekend.

It’s essentially an off-road party. The Gambler 500 is dumb, fast, drunk and totally impractical—but that’s exactly the point. You can do whatever you want, just follow the path and try not to crash. The intended route takes you on a journey through the neglected landmarks, shallow fords and forgotten towns of eastern Kansas. How you get from checkpoint to checkpoint, however, is up for interpretation.

“It’s pretty much the most redneck thing ever,” an older Gambler-er says.

Doing Something Awesome

The Gambler 500 is distinctly American. It’s the 21st century’s version of manifest destiny — open to anyone willing to take on the challenge.

And it is a challenge. You have to travel a total distance of around 500 miles in two days, stopping at 30ish checkpoints along the way. On top of that, vehicles should be purchased for $500 or less, although that’s based on the honor system and many teams spend at least that much modifying their rides. The more creative the mods, the better. It’s an expensive venture. But, then again, so is golf.

“The people are what make the Gambler what it is,” says Kansas Rally organizer Glen Jeanes. “We just give them a place and a time.”

Tate Morgan, the guy who came up with the idea in 2013, lives in Portland, Oregon. There’s a lot of empty land out there, even if there isn’t always anything paved nearby. You can do pretty much whatever you want on Oregon’s abandoned plains. People who Gamble don’t need roads. Doc Brown would be proud.

There’s a rough framework of rules — have fun, don’t be a d**k, try to obey traffic laws, etc. — but there isn’t much more to it. It’s simple and freeing, a self-governed free-for-all.

The first Gambler had only 14 participants; it was just Morgan and 13 of his buddies looking for something fun to do on a weekend. They gave each other various checkpoints and landmarks to off-road to and from. Videos got posted to Youtube. More people wanted to take part. It’s only grown from there.

Today, there are at least 35 active chapters that have hosted upwards of 50 individual rallies, held as far east as West Virginia and as far north as British Columbia. It’s been Morgan’s full-time job since he was diagnosed with testicular cancer a year-and-a-half ago. Now cancer-free, Morgan still wishes he could devote even more to his creation.

“It’s freaking amazing. It’s not making me any money, but it’s pretty amazing. I look forward to it every day,” Morgan says. “We’ve always kind of let it become what it wants to be. I’ve had people come and try to monetize this and make it like the Spartan Race, making this a big dollar thing.”

“Even the brokest dude in the world can have a piece of s**t car and that automatically qualifies you to come out and do something awesome.”

Similar rallies create exclusion through cost. The Bullrun Rally — a yearly cross-country escapade for exotic cars — costs $20,000 to register. And that’s before the costs of putting together a fancy, clean, finely tuned automobile. The Kansas rally charges just $10 per team. Some Gamblers are free: all you need is a street-legal car and driver’s license.

“That’s what makes us the most approachable motorsport in the world,” Morgan says. “Even the brokest dude in the world can have a piece of s**t car and that automatically qualifies you to come out and do something awesome.”

When the Gambler started, Morgan knew every driver. Now, there might be two thousand people at any given rally. Last year, thanks to sponsorships and memorabilia sales, the Gambler actually made some money. It wasn’t much, but Morgan’s mud derby had somehow become profitable. One of the guys who made Duck Dynastyheard about the Gambler and is trying to turn it into a Discovery Channel TV show. Although he’d love the publicity, TV time and advertisements are the opposite of what Morgan wants for his creation.

“It doesn’t have to be this big organized thing; you can just go do it,” Morgan says. “I want Gambling to be a verb, like going hiking.”

A gallery of the Gambler 500 teams

“The Gambler is the only thing we have in common. We’re all strangers when we get here.”

This is the second-ever Gambler 500 in Kansas. Glen and his wife, Mae Jeanes, handle the preliminary and clerical work: getting people registered, selling apparel and stickers, and mapping the route around eastern Kansas. They aren’t paid and have nothing to gain from facilitating the event — except a good time.

“There’s no drama. There’s no fights,” Mae says. “Plenty of times people have been pulled over, but there have been no tickets, not one arrest … The Gambler is the only thing we have in common. We’re all strangers when we get here.”

“We celebrate the weirdos and the oddball,” Morgan adds.

That’s the part of the Gambler that people talk up the most — the fraternal bond between those who never would have met otherwise. It forms when you follow other teams on the road, party the night away at the midway point, or pull someone you just met a couple hours ago out of a ditch. The Gambler oftentimes requires teams to work together.

Organizers aid the process by trying to make the route as off-road as possible. Some of the bigger Gamblers out in the Ozarks or Oregon have more freedom, thanks to an excess of public land that’s legal to drive on. Others get more inventive, like the one that goes from Southern California to Las Vegas, or the Detroit Gambler that claims to have featured more than a thousand cars.

Regardless of the location, the premise is the same: Teams just have to make it to every checkpoint, taking a selfie at each one as evidence. Nobody has ever gotten seriously hurt at a Gambler. The cars, on the other hand, take a beating.

Checkpoint 1: Switch Back Bridge

Kansas Gambler 500 Teams

Standing on the bridge on Saturday morning, Ironman — whose name is literally Anthony Stark — brags about his ride. It’s a 2005 Ford Crown Victoria that was once a cop car. It’s equipped with skid plates, a custom three-inch-lift, 30-inch tires and straight pipes that make it sound like a hot rod. Oh, and don’t forget the custom bumper that looks like it could topple a building. He’s ready.

As a 26-year-old veteran and truck-driving business owner, Ironman has the means and mechanical knowledge to be a competitive Gambler. Back home in the Ozarks — when he’s not Gamblin’ — Ironman is smashing up cars as a demolition derby driver. Behind the wheel is where he feels the most comfortable. The Gambler 500 is Ironman’s church, it’s what he believes in. The driver’s seat is his pulpit.

The morning of the race is no exception. Ironman is noticeably itching to be behind the wheel. He doesn’t want to hear the friendly reminders that all drivers should act neighborly when they encounter folks on the road. He wants to hear, “go.” The moment he and his partner are handed the list of coordinates they dash to the car. No thank yous, no wishing anyone luck. To him, it’s a race and there’s not a moment to spare.

Ironman’s audacious start ahead of everyone else is meaningless, though. A hundred miles into the first leg of the race, he’s plagued by car trouble. One of his tie rods snaps. Without it, the front-right tire is perpendicular with the wheel well. The car isn’t going anywhere.

Luckily, Ironman packs heavy. On top of the Crown Vic are toolboxes stuffed to the brim with nearly every gadget imaginable to remedy almost any problem. Nearly. Like any good mechanic, he doesn’t have all the tools he needs. But, he’s quick to come up with alternatives.

Kansas Gambler 500 Teams

“I have a s**tload of hose connectors,” Ironman says. “Let’s pop some of them on there and hopefully that can get us out of here.”

Ironman and his co-pilot strap a socket extension to the snapped tie rod, hoping it will be enough to get them 20 miles over to the next town. But, it only goes three or four before it falls apart, forcing them to wait for the onslaught of teams behind them, hoping one will have a welder.

Most people would be freaking out, calling a tow truck, and trying to figure out how to get out of the middle of the Kansas woods. Not Ironman. To him, this is nothing. It’s just part of the ride.

“This is what I do for fun,” Ironman says. “To me, this is a vacation. My friends and coworkers don’t understand it, but this is what I love.”

Checkpoint 8: Another F’n Lake

The 1984 Pontiac Parisienne, a boxy sedan akin to an ‘80s movie cop car, nicknamed “Parmesan,” sits atop a 5-inch-lift. The old steel trap is running a lot smoother than Ironman’s ride. When Parmesan pulls aways from checkpoint eight, Ironman is left behind, still waiting for a welder.

Like most bonafide Gambler vehicles, the Parmesan has had plenty of custom-work done: CB radio, custom spare tire holder welded to the back, etc. It’s finished off by an army-green matte paint job with a black Gambler insignia spray painted on the back fender.

“We painted it this color so we never have to wash it,” says Chris Wolfgram.

He and Dusty Schultz operate the Parmesan. They live on opposite ends of Minnesota and work on the car together in their spare time, splitting the costs two ways. When they aren’t Gamblin’, Wolfgram rehabs old water towers and Schultz manufactures PVC pipe fittings. Together they’ve poured blood, sweat and tears into this ride. Wolfgram’s 13-year-old son has even contributed to rebuilding and fixing it, but his son isn’t invited to the rallies.

“He’s just too young,” Wolfgram says. “Plus, this is kind of my getaway, my time to relax.”

The interior is as vibrant and creative as the outside. Green and black zebra-print felt lines the top, but the bulk of it remains untouched. It’s still as comfy and roomy as the day it rolled off the lot. No doubt, it turns some heads as it chugs along the back Kansas highways on its way to checkpoint nine.

The Parmesan, along with two vans, belong to Team Fargo Fox. Unlike other teams, they don’t haul their cars to the race. Instead, Fargo Fox opts to drive their vehicles to wherever the Gambler is happening, even if it’s halfway across the country.

“In the beginning, we were like, ‘If we’re going to do this, no trailers,’” Wolfgram says.

As of this moment, that might have been a bad choice. The Parmesan is sputtering. The carburetor isn’t regulating the fuel flow properly. The engine could stall if it slows down for even a moment. Coming to a full stop is risky; it may not start again. Unfortunately, there are plenty of potential stops as the Parmesan pulls into Wichita for lunch.

“Oh no, a stoplight in town,” Schultz says. “The ultimate test of the Parmesan.”

Wolfgram offers advice on how to operate their car in its dysfunctional state while the stop light goes through it’s full cycle – twice. “I didn’t want that green light anyway,” someone in the van behind Parmesan jokes over the CB.

Checkpoint 11: Keeper of the Plains

Kansas Gambler 500 Teams

Team Van Hail’n barely made it to lunch. After spending part of their morning spinning donuts in a creek, they start to fall behind for reasons surprisingly unrelated to team captain Logan Adams’ reckless driving.

“We blew a hose. And then we stopped in the Dairy Queen drive-thru, which took another 20 minutes,” he explains.

You can’t dampen Logan Adams’ mood when he’s behind the wheel. When lightning starts to flash in the early afternoon, he gets audibly excited with every crash of thunder.

“This is a good storm,” Adams says with a smile. Small beads of hail fall for a couple minutes early in the afternoon. His excitement doesn’t dwindle. It’s tough to damage the ‘93 Ford Econoline that Team Van Hail’n calls home.

Adams is a four-time Gambler veteran who works as a graphic designer in Kansas City. He rocks ostentatious leggings and a gaudy blonde wig at every rally, as does the rest of his team. It goes with the ‘80s hair metal theme — the van itself is painted like Eddie Van Halen’s famous guitar. They stay in character for 48 hours straight, making them beloved across the Gambler community. The wigs don’t come off until they head home.

It’s almost surprising that Team Van Hail’n’s holdups weren’t the result of something more catastrophic. In the previous rally, the van lost its front grill when Adams drove too closely to another car on a dirt road. On day two of the Kansas Gambler, the Econoline will get stuck in the mud before 9 a.m.

Not everyone at the Gambler is as rambunctious as Van Hail’n. The tamer teams dress up in off-beat costumes, drive innocently designed beaters, and follow the rules of the road more strictly. One couple dresses up as escaped convicts and drive a 1986 Chrysler Lebaron convertible designed to look like a Skittles bag. A team of husbands — The Red Rockets — races their wives — The Pickle Dicks. Two military veterans don baby masks that would give Chuckie nightmares. “We just like weird,” one of them explains.

“Everybody is randomly creative in their own way,” organizer Glen Jeanes says. “But when you put two people who are randomly creative together, they feed off of each other.”

Kansas Gambler 500 Teams
“We just like weird.”

Checkpoint 20: Halfway Camp

As car after car powers through the mud at the end of a dirt strip in a cornfield known as “S**t Road,” a squad car pulls into view. Somebody in a nearby park has apparently called the police. A sheriff walks up, peacocking with his hands clutching his bulletproof vest. He hangs around for a couple minutes, sees that nobody is really creating much of a disturbance and leaves. A minute later, somebody hears the sheriff calling the Gambler 500 competitors “cool” over the police scanner.

Kansas Gambler 500 Teams

About an hour later, everyone’s keys are finally out of the ignition. The 36 cars have racked up around 10,000 miles between them in 10 hours. The afternoon’s thunderstorms have become an outright downpour and it’s sometimes difficult to hear each other talk at the halfway camp: an unoccupied barn at the Winfield Fairgrounds in Winfield, Kansas.

A friend of the Gambler smokes 200 pounds of meat Kansas City-style. Emergency Party Services — a team that prides itself on its volume, both in decibels and quantity of alcohol provided — pulls into the barn, sirens and megaphone blaring. The second binge is about to begin.

There’s one more day of Gambling to be done, but the excitement is more-or-less over. Tonight, everyone parties and drinks and eats smoked bologna with Gate’s BBQ sauce. Tomorrow, everyone is hungover, tired and looking forward to their own beds. Everyone is spent; you can only burn a match once. The drive back to the starting point will be smooth. Everyone has a Monday. That is, until the next Gambler.

As they close in on camp, Team Van Hail’n discusses their needs for the evening. “Do we need more beer for tonight?” Adams asks.

His teammate responds in line with Gambler expectations: “Not sure. I don’t know how much we drank last night.”

Kansas Gambler 500 Teams

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