On this day‬ in 1931 one of the early crime bosses, Carmelo Fresina, died at the age of 38. He was found with two shots to the head, near a river at Edwardsville, Illinois.

Fresina reigned over the St. Louis, Missouri area with his gang, known to the police as the Pillow Gang. The name came about when a ‘sit-down’ went wrong, two of his associates were killed whilst Fresina took a few shots to the buttocks. He would then attend future sit-downs with a pillow that he would sit on.

On this day, 7th May 1931, one of the American Midwest's most colourful early crime bosses met a violent end. Carmelo Fresina, aged just 38, was discovered near a river in Edwardsville, Illinois, with two bullets in his head. His death was swift and professional — the unmistakable signature of a mob execution — and it brought a dramatic close to the career of a man who had carved out a fearsome reputation across the St. Louis, Missouri underworld during some of the most turbulent years in American organised crime history.

Fresina had established himself as a dominant force in the St. Louis criminal landscape during the Prohibition era, a period that transformed ambitious street-level gangsters into powerful crime lords almost overnight. The illicit liquor trade provided enormous wealth for those bold enough to seize it, and Fresina was certainly that. He controlled rackets across the region through his crew, known to local law enforcement as the Pillow Gang — a nickname that carried with it one of the more darkly comic stories of mob folklore.

The origins of the Pillow Gang's unusual name lay in a botched sit-down meeting, the kind of negotiation that gangsters routinely used to settle territorial disputes and internal grievances. On this occasion, the gathering turned catastrophic. Two of Fresina's associates were killed in the violence that erupted, while Fresina himself was shot in the buttocks. Rather than retreating from the rackets or showing any sign of weakness, he reportedly responded to the embarrassing injury with characteristic swagger — attending all future sit-down meetings armed with a cushion to ease his discomfort. His men followed his lead, and the legend of the Pillow Gang was born.

The St. Louis underworld in this period was not isolated from the broader national picture. This was the same era in which Al Capone was consolidating iron-fisted control over Chicago, and the groundwork was being laid for the national crime syndicate that figures such as Lucky Luciano would formalise later that same year at the infamous Castellammarese War's conclusion. Regional bosses like Fresina operated within this shifting landscape, balancing local ambitions against the ever-growing reach of more powerful interests.

Who ordered Fresina's killing and precisely why has never been definitively established, though the riverside execution spoke clearly to the ruthless consolidation of power occurring across American organised crime at the time. He remains a fascinating footnote in Midwest mob history — a man whose bravado and dark humour outlasted him in the telling, even if his reign did not.