Leatherman Takes on the Gambler 500
Leatherman Takes on the Gambler 500

Leatherman van in the Oregon forest.

During the last weekend in June, I had the opportunity to lead Leatherman’s Gambler 500 team. The Gambler 500 is an off-road event that takes place in Central Oregon every year. The event is centered around buying vehicles for $500 or less and driving them across Oregon’s trails and forest roads. The event is also a competitive trail clean-up, gathering of gearheads and misfits, and it culminates in a giant post-apocalyptic campout/party in the desert near Chemult, OR.

Leatherman engineers working on van.

About halfway through the project I was given the title “Van Dad." I suppose this comes with the territory because I was responsible not only for organizing the rebuild of the world’s saddest, rustiest van, but I was also responsible for a small family of “Gamblers." It turns out when you become the Van Dad, you get to source car parts, memorize junkyard inventories, organize schedules, handle last minute crises, plan for meals and lodging, think about safety, and most of all try to have fun while juggling all these responsibilities.

Leatherman van has a lot of rust.

Our journey started in Scappoose, OR after a very generous donation from our CEO, Ben Rivera. Ben gave the team $500 and we purchased a very tired Chevy Astro with 300,000 miles from a kilt-wearing gentleman. We were excited because we wanted a vehicle that could carry the whole team and we felt like we were embracing the Gambler spirit due to the vehicle’s price and condition. It turns out that we may have overpaid… The van needed a ridiculously long list of repairs including engine seals, an entirely new brake system, a new transmission, a suspension rebuild, and an exhaustive list of other repairs. The crusty icing on the cake was that the van lived its long life in Illinois and was absolutely caked with rust. Even a junkyard van from the Pacific Northwest might have been a better choice.

Leatherman engineer fixing the transmission on the van.

While the van turned out to be far more of a project than any of us had anticipated, it also turned out to be more fun and more rewarding than we expected. We gave ourselves roughly 90 days to build the van, but it took until the last week before our efforts truly paid off. In the final week before the Gambler, the team mounted lights, built a plywood skid plate, painted the van in Leatherman livery, replaced the transmission with a last-minute miracle (thanks to our CEO, Ben!) and covered it with custom vinyl made by Leatherman’s artists. The results of our efforts were impressive. The Astro transformed from a sad, worn out passenger hauler into a lifted, armored off-road behemoth… The Leathervan.

The Leatherman van covered in mud.

Despite the last-minute nature of our success, it turned out that the Leathervan was surprisingly capable off-road and a ton of fun to drive. Throughout the weekend, it ran through mud puddles in the Mt. Hood National forest, drove over jeep tracks in Ripplebrook, and flew down the gravel and sandy roads of Bend and Central Oregon. Over three days of adventure the only casualty to the van was a front axle and an exhaust hanger. Quick thinking by our team’s gearheads, a wire clothes hanger, and a Leatherman Free P2 fixed our exhaust system and we were back on the road. The van was our trusty steed for three days and handled anything that we threw at it. On top of being a great off-roader, it became clear that they designed those vans to be comfortable too. During our excursion it was almost hard to remember that we were supposed to be roughing it as we rode the van’s “couches" down the road. Even when we began to load the van up with trash during the trail clean-up, the van had plenty of space for the team to ride in style.

The Leatherman Gambler 500 team picking up trash.

During our trip to central Oregon we stopped at Portland’s World of Speed, dropped off trash at Deschutes Brewery in Bend, and searched for a variety of Gambler “waypoints." At each of these stops we met other Gamblers, admired their rigs, compared trash piles and traded stories about our trips. At every stop we met Leatherman fans and handed out Leatherman swag and Brewzers. We even met one Gambler that had converted his trusty Leatherman Sidekick into a key for his ride. The Leatherman spirit was alive and well amongst the Gamblers. To be a Gambler you must embrace a do-it-yourself attitude and learn to plan for the unexpected. When you take a broken-down vehicle on a thousand mile road trip, the unexpected is almost inevitable. I am sure we were not the only team of the weekend that salvaged their trip by using a Leatherman to save the day.

The Leatherman team makes it to Gambler Town.

When we finally arrived at Gambler Town, we realized the true insanity that is the Gambler 500. There were mechanical Frankensteins as far as the eye could see. Cars missing body panels and hoods, lifted sedans, hearses on 50-inch tires, and even a monster truck limousine (“The Compensator"). Gambler Town is a place that can only be understood by someone who has been there. If Mad Max, Burning Man, a Jeep commercial, and Earth Day had a child that listened to heavy metal…. It would be Gambler Town. We met some of the coolest, weirdest, and most interesting people during the night we spent there. Everyone approached Gambler Town with an open mind, a helping hand, and a special interest for cleaning up the wonderful parts of Oregon that allowed the event to happen. It is truly the strange mix of wild off-road machines, car nerds, and environmental consciousness that make Gambler Town hard to describe.

The Leatherman Gambler team standing on top of the van.

While the team made many great memories during the weekend of the event, my favorite part of the entire project was watching the team and the van come together during the final two weeks of the build. Every member of our team embodied the Leatherman spirit as the clock began to run out. Without the knowhow, dedication, and ingenuity of our team the van would not have been half of the awesome vehicle that rolled into Gambler Town. Our success during the weekend was even sweeter with the knowledge that we barely pulled it off. Watching the team react to unexpected obstacles, finish the final repairs, and dress the van up into a wannabe rally car was something to behold. As a result, everyone felt like they were truly a part of the creation of the Leathervan and walked away from the weekend excited for next year and thrilled about our accomplishment. I walked away with many great memories, a few new friends, and as the proud Van Dad of a family of Gamblers.


Check out the video from our trip!