The Gambler 500 began as little more than a way to kill a weekend. Over beers in a local tavern, founder Tate Morgan and a couple of friends laid out the guidelines for an off-road navigational challenge. The catch? Each challenger's car had to have a purchase price of no more than $500. Soon enough, word started to spread, and the guys began to receive inquiries about participation from people all over the country. By 2022, the "OG Gambler" held every summer in Central Oregon was attracting thousands of participants from all over North America. Regional events sprang up in every corner of the U.S. Along the way, Gamblers have removed over one million pounds of garbage from America's public lands. More than anything, however, the aggressively tolerant alternative to traditional car culture has become a sort of surrogate family to all manner of people. Builders, rugged explorers, and more than a few lunatics all have carved out a place for themselves in the Gambler community. Collected within these pages are just a few of their stories.