Babe Triscaro persuaded Teamsters President Jimmy Hoffa to use a portion of the Central States Teamsters Pension Fund to finance a deal to sell surplus military aircraft to Cuba in 1959. Each of the Globemaster planes was loaded with armaments and were destined for delivery in the Dominican Republic. Triscaro and his associates made numerous trips from Miami to Havana to get the deal done.
Salvatore Red Italiano headed a Italian mafia outfit that centered around Bolita, a Cuban lottery game played with 100 balls. It became a lucrative racket for Tampa organized crime. Italiano's men worked with a corrupt Hillsborough County sheriff who enriched himself and distributed the large profits among city, county and state agents. The crisis was exposed in 1951 by a U.S. Senate inquiry.