Failing To Win A Race Where Nobody Wins: The Gambler 500 Story

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The crew from Speedfreak Speed Shop showed up at the airport in Medford, Oregon, with the Harpoonigan—a 1972 AMC Javelin plucked from the Northern California weeds and off-road prepped for the 2017 Gambler 500. The Gambler is a race in about the same way the Harpoonigan was prepped for racing. You’ll understand in a minute. The car announced itself with a volley of misfires from a beleaguered 304, the exhaust huffing through rusty zoomies. The racket echoed off of the arrivals gate. With no hood, half its bodywork stripped to bare steel, and riding on meaty BFGoodrich KM2 mud terrains, it looked like a barely muzzled jackal. The Camrys and Caravans milling through the terminal gave it a wide berth.

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Just making it the 30 miles from Speedfreak HQ to the Medford airport had been something of an accomplishment, the car’s first real run after its resurrection. It was also the first time I’d met the crew from the shop, and everyone was grinning like they’d gotten away with something. Jake McDonald jumped out behind the wheel while Casey Calia took refuge from the heat and hydrocarbons in fellow Speedfreak Cody Dykeman’s Mustang. I opened the passenger door and found no seat. The floorboard looked like a Harbor Freight had vomited in there, the bare and rusting sheetmetal barely visible under a thick layer of cheap jack stands, disposable hand tools, and shop rags. A battered piston sat in the busted center console. I climbed over the tools and into the back seat. A Dale Jr. bobblehead looked on with worried eyes as Jake pointed the AMC back toward the shop. It takes a lot to scare an Earnhardt, even a plastic one. I gave a quick thought to my life insurance policy—did I have one? Dale shook his oversized noggin and looked sad.

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The Gambler rally has exploded since its inception four years ago when a bunch of like-minded friends got together, bought a passel of $500 crap cans, and went hauling off through the Oregon wilderness. Videos from past rallies show a pull-apart parade blasting through the underbrush, salvage cars of every ilk resurrected and wandering the hills on a mechanical Day of the Dead. Last year saw 31 cars descend on the mountains outside of Portland, Oregon. Tate Morgan, an original gambler and “organizer” for this year’s event says the rally sticks to a simple ethos: Have fun in your crappy car on your public land. We aimed to be a part of the mayhem with the Harpoonigan.

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Jake had spent the last three weeks getting the Javelin ready for the Gambler, usually after his normal nine-to-five. He was running on a few blinks of sleep as we scrambled to cross the remaining items off the punch list. We spent a night and the better half of a day mounting seats, running wires, and addressing the fuel system, but by 4:00 p.m. the day before the Gambler 500 was set to leave from Portland, we loaded up and left Grants Pass behind us.

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There were a few problems. That old 304 had 150 horsepower in 1972, but most of those ponies had long since gone to the glue factory. The Harpoonigan struggled to keep speed up the brutal southern Oregon climbs, backfiring and stuttering as it went. With the hood reinstalled, the temperature needle danced past 215. Whatever bushings were present from the factory had long since returned to the earth. The car bucked and swayed as it rattled up the interstate. Some 45 years of decay and oxidation went airborne with glee over traveling at interstate speed once again, and all those happy particles went shooting for our eyeballs.

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But the car was running, lapping up miles like a good mongrel for a while. Then, shortly after passing Myrtle Creek, the revs shot north, and we lost forward momentum. Jake looked down, and concern wrinkled his brow. We’d lost the transmission less than 50 miles from where we’d set off.

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The guys had overspent their budget putting the Javelin together, and now the car was a heap of slag. It was a long, demoralizing ride back to the shop, a rollback’s amber lights dappling the AMC’s baremetal hips, morale dripping from the holes in the quarter panels. Everyone loves the thought of an adventure, but a drive without adversity is just a commute. It’s how you respond to the inevitable challenge that defines the thing. You can accept the licking or pick yourself up off the floor with a grin. The Speedfreak guys are nothing if not grinning fools.

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Everyone tossed their pockets and pulled up couch cushions. We checked the drier and sweet-talked the piggy bank. Among the four of us, we had close to $500. We piled in Casey’s Subaru the next morning and thrashed north, hoping we’d find something along the way. We didn’t just get lucky. We won the jackpot, stumbling onto a 1977 Mercedes-Benz 230C just outside of Eugene.

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The car was gorgeous. Not perfect, but close. A pair of cupped hands could hold oil better than the front main, but it was otherwise straight and true. After some negotiation and a visit to yet another ATM, we shook hands and passed our $475 hardly earned dollars to the former owner. All that was left was a fun conversation with my wife about how I now owned a majority share in a s**tbox Mercedes 2,800 miles from home.

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We were gambling again, this time in an ancient German car with 272,000 miles. The previous owner waved us off, counting our hundreds as we headed to a Home Depot for masking paper, tape, and six cans of matte black Krylon. Jake sprayed the hood in the parking lot, ripped the three-point star off the grille, and dropped the Convoy duck off the Harpoonigan in its place. At least part of the original car would make it to the start line.

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The drive to Hoodoo Ski Area was sublime. Summer in the Pacific Northwest is a gift, an eternal spring when the temperature stays cool and the sky stays clear. Everything is green, the air dark and sweet with the smell of cut hay and living rivers. The Mercedes was glad to be off its heels, the little four-cylinder humming along out ahead of us. Everything worked. Every light, every gauge. The horn. The heat. We didn’t know what to do with such luxury, so Casey entertained himself by brandishing a cavalry sword at traffic from the rear window.

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We were a day late by the time we made the official Gambler camp, and although there are no real rules, organizers generally encourage participants to make the start. We had no registration, no GPS waypoints, and no clue about where we were supposed to be or when we should be there. The main parking area was full to the brim with gamblers, and those who’d wandered in late lined both sides of the road leading to and from the lodge. It was like catching a glimpse of the first days following civilization’s collapse, or the complete physical manifestation of the libertarian ideal. The only tech inspection at the Gambler 500 is your own thin sense of self-preservation, and it shows. Forget seat belts, most gamblers see doors as optional equipment.

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The party was already in full swing by the time we arrived. Small fires gleamed off of pitted chrome. The clink of beer bottles punctuated bouts of laughter echoing through the darkness. Someone was setting of firework mortars, and the blooming displays lit the rows of parked gamblers like crooked and broken teeth. We found some sympathetic souls to let us take a photo of their waypoint list before the beer curtain fully descended on all of us.

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It was hard to fathom the number of cars piled in and around Hoodoo. Tate Morgan said that 749 vehicles preregistered, but there were more than 850 in attendance, including a full-size city bendy bus with no glass but a functional hot tub. Another bus served as a mobile tattoo parlor, $60 minimum. Cannonball Casey was in full effect, wandering the crowd with a bag of sangria like the Saint Nick of intoxication. There was a man getting a nipple tattoo on the bus, clamoring for a drink. Casey banged on the window until it slid open.

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“Oblige him,” he said in his best Aldo Raine and thrust the swollen sack of regret through the window. The man suckled at it with gusto. We roamed the rows of rusting hulks before retiring to our villa for the night. I can say with some confidence that a ’77 Mercedes will sleep four adults with minimal contact and relative comfort.

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In the morning, I found Casey’s sack of sangria splattered on the pavement in front of a lifted, four-wheel-drive ’78 Lincoln Continental limo on 35s. I couldn’t sum up the Gambler 500 any better if I tried.

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Judging from our blurry cell phone camera waypoints, organizers gave gamblers three route options: easy, medium, and broken metal. When the medium route proved to be little more than windy back roads, we aimed the Convoy duck toward the hard stuff. Even laden with four guys and a trunk full of tools, the 230C took it all in stride. Later, I found out that Mercedes sent a 280C on the London-to-Sydney rally in the late ‘70s. It didn’t just finish. It won the thing.

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There are no winners at the Gambler 500. Or maybe everyone’s a winner. It’s hard to tell. Our day devolved into the sort of antics usually left for high schoolers with a fresh driving permit and no concept of mechanical sympathy. We bounced down gravel roads, stones plinking off the car’s underside as we motored. We bounded through potholes as deep and wide as the car, the muffler and spare tire well flattening as we went. We blitzed through the underbrush for an hour or more only to exit into a clearing to find a waypoint packed with madness, lifted Toyota MR-2s parked alongside Lincoln Continentals on Mud Terrains and back-halved Crown Vics. Mount Hood’s snow-capped peak was shining in the distance. Everyone took turns behind the wheel, cracking each other up and slowly falling in love with the little German that could.

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We caught other gamblers or they’d catch us, everyone waving and laughing at everyone else’s merry stupidity. There wasn’t one of the vehicles in attendance that wouldn’t raise an officer’s ire under normal circumstances. We were swimming in the deep and wonderful waters of gray legality, a school of vermin thriving on hive theory. Not one cop could catch us all.

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We followed our waypoints out of the mountains, bumbling toward Portland and the Gambler charity car show, following the convoys of other crusher escapees. A cynical eye would say we had no business being there. We’d missed half the rally, after all. But the Speedfreak crew hadn’t let up when their chips vanished and their plan went up in smoke. They’d doubled down, flipped off the house, and gone all in. They stayed gambling, and it was worth it.

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There’s something blissful about that rally. Maybe it’s the lack of pretension, competition, or organization, or the simple joy of giving in to your high school self, grabbing some goons and whatever car you can get your hands on and going for broke in every conceivable meaning of the phrase. As we aimed the Mercedes south again, we found ourselves eying every oddball car on the road and thinking, “Yeah, I’d gamble that.” A street sweeper? Why not? A mid-80s conversion van? Absolutely.

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The Speedfreek guys already have an ace in the Harpoonigan. It would take the crew less than a week to get the thing off its haunches and back on the road. There’s a winter Gambler to attend, and Jake and the guys are busy shaking the thing down and making certain it’ll handle more than 50 miles.

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I dropped the guys off at Cody’s house in Eugene, turned the Mercedes right around, and drove straight on to Salem. I couldn’t believe how willing the car was or how it was such a genuine joy to drive. I couldn’t let it go. After ambling all the way to Seattle, I bought out the rest of the guys and aimed the car east. All the way to Virginia, the rally’s mantra was on my lips over every mile as I wandered out of Washington, across Idaho, and into Montana: Always Be Gamblin.

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NOTE: Fred from Dirt Every Day did it too! See that on Motor Trend on Demand.

Roadkill Fall 2016 Cover