Automobiles Winter Gambler 500: An Off-Road Adventure with $500 JunkersA fleet of $500 lemons cruise 500 miles while picking up trash and discarding junk along the way.

Words Zach Bowman
Images Jenny Linquist

It’s cold and dark and raining as we drive out of downtown Portland. The sun won’t rise for an hour, but we’ve got a meeting to make at some truck stop along I-5. The O.G. Gamblers are rallying there, filling the fuel tanks in their oddities and shitboxes in preparation for the Winter Gambler 500.

The concept is simple: entrants bring a $500 car to take part in a 500-mile, point-to-point rally that runs through a tangle of forest roads. The event relies entirely on individual honor, self-preservation, and the associated vagaries. There is no central governing body, and no one is interested in checking papers or bills of sale. There is no “first place” or any other prizes to speak of. It’s simply the thinnest excuse you need to go out into the gorgeous Oregon sticks and be an idiot — and to have the kind of fun that isn’t illegal yet, but might be soon.

We’re riding in a 1971 AMC Javelin stitched together by Jake McDonald and the crew at Speedfreak Speed Shop in Grants Pass, Oregon. It’s a wasteland reject, stripped bare of paint, its sheet metal gleaming under the orange street lamps as it snarls down the highway. The engine’s best days are behind it. Of its eight cylinders, maybe five function. It blats and coughs through a pair of rusty, upturned exhaust pipes, which almost drown out the drone of the 30-inch BFGoodrich Mud Terrain tires. The floorboard is littered with tools, parts, and weapons: a fuel pump, a crowbar, and a machete are all within reach. There is no heat and the seat belts are eBay specials with “REPLICA” clearly stamped on the buckles. It is a miserable disaster, and it’s fucking perfect.

(1) Author Zach Bowman riding passenger with driver Jake McDonald of Speedfreak Speed Shop.

He is the portrait of a Gambler, grinning mad astride his dead horse, its front right wheel dragging and flopping with all the grace of a compound fracture.

Other Gamblers are at the truck stop when we arrive. A lifted Mercedes E300 lurks near the front of the convenience store. A towering, diesel Chevrolet Nova on a Blazer frame hunkers on the far side of the pumps. A six-wheel-drive Pinzgauer and Battleship 1978 — a lifted Lincoln limo on one-ton axles — take up an acre in one corner of the parking lot. The Javelin has found its people. Tate Morgan, the Gambler 500’s unofficial mad conductor, has yet to show up in his long-arm Miata. We met him yesterday at Gambler HQ in Portland, the air thick with welder smoke and ozone as he attempted to stitch a wide piece of steel to the nose of a whipped Corolla.

We hadn’t known him five minutes before he flipped up his welding mask and looked our way. “You guys driving tomorrow? You want to? I’ve got a Blazer you can borrow.” The man is a born enabler. Five years ago, he was working a high-profile job in distribution and sales. One night over beers, he and a friend came up with an idea that would become The Gambler. He admits the thing started as a race. The early years were set up like a time-speed-distance rally. “It was me at a bar at the end calculating everyone’s times, but what we noticed was that the people who weren’t racing, who brought the dumbest thing — they were having the most fun. People like me and my buddy Chuck who were peeing in bottles and not slowing down? We were the ones stressed out.”

And stress wasn’t what Morgan needed. A year after the first Gambler, he was diagnosed with testicular cancer. “I couldn’t sleep at night. This was a nice distraction from all that. I just poured my energy into this. Everybody asked if they could come. Sure, you can come, but if you’re in Virginia, why don’t you just start one there? You can get your shithead buddies together and I guarantee you’ll have just as much fun.”

Now Morgan is cancer-free and there are 43 independent Gamblers operating all over the United States. “We said, ‘Here’s the logo, here’s the name. Use it so you can attract the right people, so they know what to expect when they go to a Gambler.’ They’re not lighting the fucking place on fire or leaving cars out in the woods. They’re coming to do this cool thing.”

It’s more than just a horde of knuckle-draggers scraping through the woods. The Gambler makes it clear: you’re there to enjoy your public lands. You’re there to take care of them. Last summer’s rally saw 850 cars dive into the Oregon wilderness. And because the event encourages participants to pick up whatever trash they see, Morgan calls it the largest trail clean-up in the state’s history.

That was this summer. Today, the sun never quite gets to rising; the sky just tilts from black to gray while we raid the gas station for bad coffee and breakfast. When it comes time to leave, trouble sets in. The Javelin has never needed a key to start, but it wants one now. The steering column is locked and the ignition won’t turn.

I haven’t busted a tumbler since I was 15, but some lessons can’t be unlearned. McDonald produces a hammer and a screwdriver from a pile of tools behind the driver’s seat, and I start wailing on the steering column. He looks up a wiring diagram while bits of pot metal clatter to the floor. A crowd of Gamblers hear their call and gather around to watch the lunacy. We have the car running again by the time Morgan pulls into the parking lot, a roof-top tent strapped to his roll cage. He and his co-driver are wrapped in rain slickers, their only protection against the Pacific Northwest winter. Later, I try not to bitch about seeing my breath in the Javelin’s passenger seat or the rain dripping from the holes in the roof.

The caravan to the official start is a miracle parade of the derelict and near dead. Other Gamblers catch us on the road or we catch them. Everyone’s having a blast until we realize our hot-wiring job skipped over necessary accessories — like the windshield wipers. We jump the terminals while rolling down the highway, satisfied by our ability to pry functionality from entropy’s cold grip.

The day goes that way. We sign our waivers and collect our waypoints, the morning passing in a haze of spent hydrocarbons and nicotine. We MacGyver the alternator with a folded business card and pop the hood in traffic to keep the old V8 from melting to slag. No one’s letting this bastard lie down and die.

The weather settles into a thin drip, the air flirting with freezing as the clouds drape themselves along the conifer hills. As we parade out of Cascade Locks and cross into Washington at the Bridge of the Gods, the Columbia River looks small and dark below us. Even with the cold and the wet, we’re wired with the absurdity of what we’re doing, of chasing a Pinzgauer through a small town in an AMC with off-road mudders, a zip-tied CB radio crackling at my knees, a Dale Jr. bobblehead nodding his approval from atop the dashboard.

We face our first obstacle when the route takes us onto a climbing two-track. The road dissolves into deep, muddy ruts. It’s a litmus that splits the train of salvage yard rejects in two. There are those like McDonald who have to drive their machines 200 miles home, whose sense of mechanical sympathy runs wide; and there are those like Morgan, who hit that hill full throttle. The shriek from the Miata’s little four-cylinder fills the sky. As I hike up to watch it struggle, I nearly catch a flying softball-sized rock with my face. The Miata flings stones in a shotgun spray, its tires spinning and smoking, fighting for grip, and losing.

The road gives way under Morgan’s front right wheel, a waist-deep hole opening up and swallowing it.

We turn and follow a string of high-voltage power lines instead, the forest carved bare to make a path for them. Below us, the river shines with a rare, thin thread of sunlight — a perfect place for what’s about to unfold. The road gives way under Morgan’s front right wheel, a waist-deep hole opening up and swallowing it. The unexpected drop snaps the car’s tie rod, and by the time we arrive on the scene, a minor army wielding torches, taps, and J-B Weld have descended upon the car. Morgan’s muddy to his hips and frustrated. And when it inevitably comes to pass that no amount of half-assery is going to reattach that wheel to the steering system, he tells the assembled crowd to go on. He’ll wait by himself for the tow truck.

No one makes a move to leave. When there’s nothing to win, there’s nothing to lose by standing. We’re in a perfect place to crack a beer and bullshit until the tow truck arrives, the crowd laughing and taking the time to pick up whatever trash it can find. Someone hooks the Miata to the back of the Pinz and the six-wheeler hauls it up to the trailhead, Morgan calmly sitting on the car’s fender. He is the portrait of a Gambler, grinning mad astride his dead horse, its front right wheel dragging and flopping with all the grace of a compound fracture.

The tow truck takes its sweet time. We spend the better part of six hours on the side of that mountain watching the other Gamblers come ripping through. The Subaru BRATs and Volkswagen Vanagons, the back-halved Crown Vics and PT Cruisers. It is a perfect spectacle, but it’s nearly dark by the time we point ourselves west and gun for camp. Sunset brings weather: great sheets of rain pour down on Highway 6, the crooked two-lane that ducks its way up and over Tillamook State Forest. The Javelin’s cobbled wipers are woeful. The windshield goes opaque in the face of oncoming traffic, and we spend our time flirting with the guard rail one second and the double-yellows the next.

But we make it. We find ourselves a swampy spot not far from the barbecue and the live band, crack a flask and breathe. We laugh at our good fortune of simply not dying. It’s early, despite the dark, and we wander the long lines of forsaken automobiles. The band echoes through the trees as we marvel at the collection of fools like us who left a warm couch behind to poke Fate in the eye. Fools who prefer a handful of dark and hilarious “maybes” to a certain and safe weekend. Fools who’d rather go down gambling.