The Gambler Last Man Standing provides every runner with the same 2-mile loop at Oak Mountain State Park in Pelham, Alabama, continuing until only one participant remains. This lap-style trail endurance race, typically held in February, follows a straightforward rule: finish each lap within the allotted time or be eliminated. For the initial 50 laps, participants have 40 minutes per lap, covering 100 miles before the time limit changes. Subsequently, the limit decreases by 2 minutes each lap, poker chips are no longer awarded, cash-out opportunities cease, and pacers depart the course.
The loop consists mainly of trails, incorporating brief road sections and a stretch alongside the lake. Each lap accumulates 183 feet of elevation gain. Runners receive a poker chip for each completed lap up to 50, then decide at specific mileage intervals whether to redeem their chips or add them to the Last Man Standing Bucket. Support crews and personal aid stations are situated at the start/finish area, with no assistance permitted on the course itself. Pacers are allowed only between miles 20 and 100, with one pacer per runner at any given time. The event is cup-free, requiring runners to carry their own hydration vessels, and the final prize bucket is awarded to the runner who completes the last lap solo.