The first thing you notice about the mug shot of Samuel R. Caldwell is that the man is wearing overalls. The balding, middle-aged Caldwell’s brow is furrowed, his lips tightly pursed. “Colo State Pen 18699” hangs around his neck, snug to the top of his tightly cinched denim shoulder straps. His eyes stare defiantly into the prison photographer’s lens, just shy of seething. A few years after the photo was taken, the serially incarcerated Caldwell would be picked up by police at a Denver flophouse and sent to federal prison in Leavenworth, Kansas. There he served four years for an act that had become a federal crime just a few days before his arrest on October 5, 1937: selling marijuana.
In the decades since, Caldwell has become an unlikely poster child for cannabis legalization advocates. His mug shot adorns t-shirts, posters, and coffee cups canonizing Caldwell as “The First Pot POW.” Although Caldwell was undeniably early collateral damage in America’s war on drugs, his story isn’t a straightforward march to marijuana sainthood. In fact, it’s quite messy.
A laborer with an 8th grade education and a lengthy rap sheet, Caldwell was hardly the innocent farmer that his overalls might suggest. He was, in the words of one of his prison evaluations, a “career criminal” and former bootlegger who owned more than just the four pounds of cannabis found in his Lothrop Hotel room on Denver’s Laurence Street. Caldwell also possessed a comically bad sense of timing. According to one of his friends, the 57-year-old Caldwell had only begun selling marijuana a few months before the new federal law kicked in. It was a pure financial play—he never smoked the stuff. Four years earlier, in January 1933, federal agents arrested Caldwell for selling a gallon of contraband whiskey for $5—less than a year before the 21stAmendment overturned Prohibition. Caldwell’s first tour in Leavenworth was for peddling white lightning, not Panama Red.
This much is true: Sam Caldwell was one of the earliest targets of the 1937 Marihuana Stamp Act. But in point of fact, he was not the first.