Plumeri became a member of the crime family of Gaetano Reina in the 1920s and was first arrested in 1923 on various charges. In the 1940s, he was promoted to the rank of capo. Plumeri was an associate of Louis Buchalter and Lepke's partner Jacob Shapiro, who were affectionately known as "The Gorilla Boys" and the uncle of notorious gangster Johnny Dio. Doyle and Dio started a garment workers trucking association, whereby the truckers working in the Garment Center were forced to join the trucker's union headed by them and of course, the "union dues" never made it into the union's coffers (it went straight into Dio and Doyle's pockets instead), and phony books were established to satisfy whomever decided to inquire about the trucker's union's financial solvency.