Chester 'Checkers' Spears was an ex-Army veteran who formed the party of mercenary and helped orchestrate a coordinated attack on the Dutton Family.
In 2006, Checkers was dishonorably discharged from the United States Army for conduct unbecoming. Now he's just does freelance work around Montana and is connected with the Montana Free Militia.
While he was gambling away the money he was paid at the Painted Horse Casino, he was rambling to the card dealer about how he was involved in the hitjob. Mo and the rest of Thomas's security quickly picked up on that and dragged him into the wilderness. Mo held him prisoner in his tool shel for a few days until they relinquished him over to John Dutton, who personally drove him out to the Train Station and gave Checkers a fighting chance. Unfortunately, Checkers was killed by John and fell dead into the canyon.