The first owner of the Santurce Crabbers, Pedrin Zorrilla, was a visionary, with many Negro League and big league contacts (he signed up Josh Gibson, Satchel Paige, Roy Campanella, Ray Dandridge and Leon Day in the first decade). Santurce was the most successful winter league team of the 1950s, with three Caribbean Series titles. Roberto Clemente, Ruben Gomez, Willie Mays, Willard Brown and Bob Thurman played for the Crabbers. Tom Lasorda used to pitch for them.

Santurce set up working agreements with the Giants, Orioles, Dodgers and Astros, among other teams. Earl Weaver and Frank Robinson were team managers; several Hall of Famers were early-career Crabbers. Orlando Cepeda and Tony (Tany) Perez played their entire winter league careers with Santurce.