One of the earliest Italian gangs was the Pillow Gang that began operating in the city around 1910. The gang’s name came from its leader Carmelo Fresina, who carried a pillow with him to sit on after he had been shot in the rear end. Years later Senator Estes Kefauver would sum up Fresina’s career, “Eventually Fresina, an extortionist and bootlegger, was dispatched with two bullets in the head and no longer needed his pillow.”

According to historian Walter M. Fontane, between 1910 and 1914 there was an ongoing battle between Italian factions in the city that left 10 dead and several survivors deported. “Freelancing became the way of the Mafia” until new leadership came in the name of Dominic Giambrioni in the late teens. After the arrival of the Giannolas, Giambrioni was forced out in 1924. He returned 10 years later and was murdered. In 1922, Fresina arrived and joined the faction headed by Pasquale Santino. After Santino was murdered in 1927, Fresina took over the gang, which became allied with a maverick splinter group of the Green Ones led by Tony Russo. Together they waged a battle with the Green Ones.

In January 1929, after the Giannolas had been eliminated, Fresina and two members of his gang attended a meeting at the home of a Russo faction member. It was rumored that Fresina had made peace with remaining members of the Green Ones and the Russo faction felt they had been betrayed. In a wild shooting Fresina was wounded in the buttocks and his two associates killed. The Russo Gang, already depleted due to the deportation of three Russo brothers in 1928, continued to do battle with Fresina and the Green Ones until their faction “disintegrated” around 1932. Pillow gang members then turned and fought the Green Ones again after they blamed them for the death of Fresina, who was killed near Edwardsville, Illinois in 1931.