When I first met Tate Morgan a few years ago, the founder of the Gambler 500 was munching on some snacks from a Meow Mix bag. “That can’t be actual cat food,” I thought. To this day I’m still not sure what was in that bag, but it was a precursor to the irreverence I would find at the Gambler 500.
What started in 2014 as an actual race with 28 folks vying for dominance in crapcan cars through the backwoods of Oregon has morphed into an international trail cleanup with thousands of participants around the world.
As more people heard about the Gambler 500, Morgan decided to incorporate his passion for land stewardship. “I wanted to gamify it and make it fun, like Mary Poppins,” he says. “Instead of speed, I’m using trash as the winning metric.”
Not that there isn’t any racing at the Gambler 500. With a modicum of safety gear, gamblers can run their cars in the HooptieX series. Think Lemons but for racing cars in worse condition, and in dirt.
For the Gambler, you only have to remember one rule: “Don’t be a d*ck.” The website is intentionally vague but includes waypoints to help guide Gamblers to trash-strewn locations. Pick it up and bring it to Gamblertown during the day, then party at night. Repeat until the weekend is over.
There are small Gambler events all over the country, even reaching into Mexico, Canada, and Iceland. But the one outside Redmond, Oregon, is the OG. This year a ragtag group of 8000 or so people pulled nearly 500,000 pounds of trash out of the woods, including eight boats, 12 campers, and a full-size school bus.
The folks that come out to the Gambler 500 are as varied as the cars they bring. I chatted with a few of them to learn about their builds and find out what keeps them gambling.
Jake McDonald: The Veteran
McDonald’s first Gambler was in 2017, when the event was still a vague, shimmering, unfindable event with a secret-handshake mystique. Word on the street was that you had to buy a specific T-shirt at a specific time in order to join in. McDonald did, only to be told it was a joke and all you had to do was show up.
His first and only Gambler car is a 1972 AMC Javelin. You can find pristine examples of Javs for upward of $30,000, but McDonald’s rig doesn’t have nearly that much juice. After the stock motor and transmission went to that great junkyard in the sky in 2020, McDonald replaced it with a small-block Chevy powerplant he found on Facebook Marketplace for $100.
He mounted the whole engine up high for more ground clearance—the Magnacharger supercharger thrusting up from the hood is just a bonus—and added an MSD ignition. Front disc brakes make the car almost safe, and the Javelin wears 30-inch BFGoodrich all-terrain tires.
McDonald has touched almost every part of the car except for the body, which becomes evident when I see the giant rust holes in the trunk. Still, the car is strong enough to haul a trailer loaded with two mini-bikes and a go-kart on the four-hour drive from his hometown of Grants Pass, Oregon, to Gamblertown, with the patina of rust, mottled paint, and stickers attracting attention the whole way.
C.J. Cromwell: The Visionary
Cromwell showed up to this year’s Gambler 500 without a car. A freelance MacGyver who’s a fabricator and mechanic, he used his trip to deliver finished projects to non-Gambler customers and didn’t have room on the trailer to bring one of his famous builds, like the Trophy Mutt.
You haven’t heard of the Trophy Mutt? It’s a replica of the Mutt Cutts van from Dumb and Dumber, except it’s built on a highly modified Geo Tracker chassis with the ability to sail through the air like a champion frisbee dog. It’s famous. Where have you been?
Okay, but surely you’ve seen the Plybertruck. Cromwell beat Elon Musk to the punch with an Acura MDX skinned with plywood to match the Cybertruck’s futuristic design. It’s not electric but it is running on public roads, so we’re giving him the win.
From a Jet Ski on a motorcycle to a boat on a car chassis, Cromwell is the guy for creative Gambler builds. His showing up without a car is akin to Santa Claus sliding down the chimney with an empty bag. What the heck, Cromwell?
The heck is time, my friends. We can never get enough of it. Cromwell put his mettle to the test with an overnight HooptieX build.
After delivering his customers’ cars on Saturday, he found a Hyundai Accent on Facebook Marketplace for $400. “In the Marketplace photo the car was on its side, so I knew it would be perfect,” he says.
After a baseline loop around the HooptieX course, Cromwell went to work with his easy-breezy 3.0-inch lift courtesy of four grade-eight bolts and some scrap metal. Tennis balls were added to the strut springs for a bit more height, and a set of slightly larger tires were thrown on for good measure. It wasn’t fancy, but come Sunday morning, Cromwell cut 30 seconds off his HooptieX time, teaching us that sometimes the simplest modifications can have the most effect.
Tyler Merrill: The Greenhorn
Merrill tried to buy his Gambler car when he was 14 years old, but the owner refused to part with it. Fast-forward 20 years or so, and Merrill now owns that dream car, a 1958 Plymouth Savoy named Maxine.
Merrill procured the car as payment for helping clear a scrapyard. In perfect Gambler form, the thing was already set up as a dually. The previous owner had installed bull bars in the front and rear and used Maxine to push loads around the scrap yard. Merrill did the obvious and threw the body on a truck chassis, keeping the dual-rear-wheel setup.
Under the hood is a 12-valve Cummins turbo-diesel pushing out about 1000 pound-feet of torque. The Tremec TR4050 five-speed manual transmission can only hold about half that, so Merrill says he’s destroyed quite a few clutches. Fortunately, a six-speed NV 5600 is waiting in his Utah shop for installation.
Merrill drives Maxine—a nod to both Mad Max and the Stephen King horror novel Christine—a few times a week, getting waves, giving out stickers, and thumbing his nose at anyone who’s too uptight to enjoy a monster mashup.
“This was a junkyard dog,” he told me. “I took this old, beat dog and gave it new life.”
Come for the Garbage, Stay for the People
Despite the differences in their cars, all three of these Gamblers have a similar reason for coming out, and it proves Tate Morgan’s point about the importance of making an unpleasant task, like off-road stewardship, into a party.
McDonald likes the type of folks the Gambler attracts, saying, “This event filters in people you want to be around.” He gestures to the camp: “This would not happen in a bar or supermarket or when you go to the gym.”
Cromwell likes how the Gambler format makes camping and off-roading accessible and safe. “This is my sanity. It’s my support team to be able to travel and not do it alone and make it cheaper and easier,” he says.
I have to agree. I arrived at the Gambler 500 by myself and was immediately welcomed into any camp I chose. Beverages, both adult and otherwise, were offered, as was food and mechanical advice. One guy even gave me a T-shirt with the words “Race Car Driver” emblazoned across the front for no reason other than that he thought it would make me smile.
However, it’s Merrill who sums it up best. “I’ve met so many friends that I never would have talked to otherwise. The Gambler attracts true salt-of-the-earth people and it always throws away all the things people tend to argue and fight about. You belong here. Everything is good.”
How to Become a Gambler
If you want to Gamble, check out the Gambler website. If there isn’t an event in your area, Morgan allows anyone to use the moniker as long as garbage is collected and nobody profits from the event.
If you come across large pieces of trash while out exploring that you can’t haul away yourself, you can mark it on the Sons of Smokey app. Conversely, if you’re longing to test the pulling power of your new Hummer EV, check the app to see if there is any garbage nearby that you can haul away.
Finally, back to the Meow Mix. In the early days, Morgan named the company as a fake sponsor of the Gambler 500, and instead of rolling with it, Meow Mix had a less-than-positive reaction. Morgan doubled down with the snark, and that’s why he was eating snacks from a Meow Mix bag.
At least that’s what he says. It might still have been Ocean Explosion. Typical Gambler behavior.
Senior Editor, Features
Like a sleeper agent activated late in the game, Elana Scherr didn’t know her calling at a young age. Like many girls, she planned to be a vet-astronaut-artist, and came closest to that last one by attending UCLA art school. She painted images of cars, but did not own one. Elana reluctantly got a driver’s license at age 21 and discovered that she not only loved cars and wanted to drive them, but that other people loved cars and wanted to read about them, which meant somebody had to write about them. Since receiving activation codes, Elana has written for numerous car magazines and websites, covering classics, car culture, technology, motorsports, and new-car reviews.
