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The CBWS was the brainchild of the Venezuelans Oscar "El Negro" Prieto and Pablo Morales, who devised the idea after the seeing the success of the Serie Interamericana (Inter-American Series) in 1946, which featured the Sultanes de Monterrey from Mexico; the All Cubans from Cuba; the Brooklyn Bushwicks from the United States; and Cervecería Caracas from Venezuela. The Bushwicks won each year from 1946 to 1949, but Cervecería Caracas won the final Serie Interamericana in 1950.
Inspired by the Serie Interamericana, Prieto and Morales presented their idea for a CBWS to a Confederación de Béisbol del Caribe (CBC, Baseball Confederation of the Caribbean in English) conference in Miami in late 1948. Cuba agreed to host the first series, which would feature the top team from each of the CBC member nations — Cuba, Panama, Puerto Rico, and Venezuela — in a six-day series of doubleheader games to determine the winner.
The series ran annually from 1949 to 1960, with Cuba winning seven times. However, the CBWS was cancelled after Fidel Castro dissolved all professional baseball in Cuba in 1961, replacing the professional teams with a state-run amateur system. It wouldn't be until 1970 that the CBWS was revived.
The Series, which is usually played over six days, typically features up to six games per team, although some series have had games cut from or added to the schedule. The winner of the series is the team with the most wins after each team plays six games.