Always Be Gambling

A 500 mile Oregon off-road r̶a̶c̶e̶ navigation challenge

When your buddy tells you 3 days before the Gambler 500 that we’re going to buy a car for $400, register it, plan, pack, and drive that p.o.s. 500 miles through some of the most rugged Oregon terrain to collect waypoints and camp out, the only appropriate response is…“Cool, I’ll Venmo you.”

Above is Sheila, the most important member of Team Real Loose, a band of misfit road warriors destined for Gambler fame. Sheila is a 1992 Subaru Loyale, and judging by how well it took the ass-beating we gave it, probably the most well built vehicle of the H. W. Bush era.

The Gambler 500 is Burning Man meets Thunderdome. They can’t legally call it a race, but nor should they, because it is not about being the quickest team to hit all waypoints. It’s about gambling — with your money, your sanity, and your life.

But the Gambler is more about adventure, camaraderie, and exploration of wilderness, than a road challenge. I regularly gamble as a hobby, so this event was awesome. Thanks to David and Drew for pioneering, going to pick up Sheila, and painting it like a 90’s hair metal icon.

Even before the event started I was changing a flat tire. Can you tell which tire was the “good one”? Me either. What could go wrong?

The Oregon challenge took off from Portland Meadows, where over 700 cars gathered to head off across the state. The previous year they had 31 vehicles. So, I think in terms of events, the Gambler has hit upon a nerve. I assume next year they will tap that nerve and milk its for all it is $worth.

The rules were vague and almost non-existent on purpose, which is just how I like my rules. We were given options of three levels of waypoint routes (Long/Lat coordinates) to choose from. We chose the most difficult — called “Devil’s Butthole”, presumably because after driving into the Devil’s butthole it would be difficult to get out.

After a long wait while they spaced out staggered starts, we were released into the wild, only after we cut the line — We were gambling, after all.

Once on the road, we unanimously gave ourselves a 95% chance of not even making it out of Portland. For one thing, to drive in a straight line our steering wheel had to be turned and held exactly 20 degrees to the right. We were riding on cartoonishly small tires, had no power steering, about 4 inches of clearance, and the engine would not allow us to go over 55mph on the highway — which was fine because we were swerving all over the road like a fish out of water from a total lack of alignment.

The front passenger side window did not go down, and it was hot. So, we ripped apart the door and manually cranked it down.

These were mere minor setbacks in the early innings. We forged on and made it to Mt. Hood! If we were forced to go home then, we’d have flown our mission accomplished banner at Govt. Camp and headed home heads high. But we were just getting started. We gambled off to find our first waypoint on the East side of Mt. Hood National Forest. The route we took was down the Barlow Road. I was familiar with this trail, so I did not hesitate to put Sheila on the offensive. With Steel Panther blaring on the 1992 dolby system, we force fed Sheila some dirt and made haste.

We made it in one piece, with newly emboldened confidence in Sheila’s ability to take an absolutely brutal verbal and physical beat down.

We celebrated with “some” beer, and quickly gambled on to the next waypoint in Maupin. All along the trails there were beautiful sights and lots of other gamblers to ride with.

We were almost to the mid-point camp area at Hoodoo, where all the gamblers were gathering to camp. Instead of camping with everyone in a predestined spot, and in keeping with the true spirit of the event, we threw down some more chips and gambled on finding our own spot. With the sun going down we hustled to Santiam pass to search for a nice clearing.

Though no water, we did find a spot with a wide clearing for maximum Milky Way viewing.

We spent the night listening to Yani, and watching “the David show” — which basically consists of one hilarious joke that lasts continuously for 6 hours, or until he passes out.

Woke up the next morning, made some eggs and bacon, and packed up, ready to do some more gambling.

With the first day behind us as an incontrovertible success, we entered day 2 determined to break Sheila.

We were beginning to think she was the Bruce Willis of cars. Aside from us totally shattering her shocks, and changing tires 4 times, she was purring like a Hyena in heat.

Turns out, not only was Sheila unbreakable, she was actually rescuing other gamblers who were stuck in the mud. The Gambler crew gave out awards, but we definitely think they missed an important category of “100% stock” vehicles. We were pulling “non-stocks” out of thick mud!

With two more waypoints under our hood we headed for home, and rode our beastly chariot victoriously onto the Portland Meadows lawn.

Overall the event and Sheila far surpassed our expectations. We actually ended up giving Sheila back to the owner we purchased from for free, which felt awesome. What upstanding citizen hasn’t wanted to absolutely beat the shit out of a rental car before returning it?

We’re definitely doing the Winter Gambler, and I’m already thinking about what vehicle to mod for next year.

We learned a lot about ourselves on this epic journey. Just kidding, we didn’t learn a thing.

Life’s a gamble. Always call its bluff.