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The Pittsburgh Pirates were founded in 1881 as a member of the American Association, a rival league to the National League. The team quickly established itself as a force to be reckoned with, winning three straight pennants from 1901 to 1903.

In 1903, the Pirates faced the Boston Americans (now the Red Sox) in the first modern World Series. The series was a best-of-nine format, and the Pirates won it in eight games. The Pirates' victory made them the first team to win a modern World Series, and it established them as one of the premier franchises in baseball.

The Pirates continued to be competitive in the early 1900s, thanks in large part to the contributions of legendary players like Honus Wagner and Fred Clarke. In 1909, the team won another World Series, defeating the Detroit Tigers in seven games. The Pirates' victory in 1909 is often cited as one of the greatest upsets in baseball history, as the Tigers were heavily favored to win the series.

The Pirates remained competitive throughout the 1910s and 1920s, but they did not win another pennant until 1925. That year, the team won the National League pennant and faced the Washington Senators in the World Series. The series was a classic, with both teams winning two games apiece before the Pirates won Game 7 by a score of 9-7. The victory gave the Pirates their third World Series championship.

The Pirates continued to be a competitive team throughout the 1930s and 1940s, thanks to the contributions of players like Arky Vaughan, Paul Waner, and Lloyd Waner. In 1946, the team won the National League pennant and faced the Boston Red Sox in the World Series. The series was notable for the debut of Jackie Robinson, who played for the Brooklyn Dodgers in Game 2 at Forbes Field in Pittsburgh. The Pirates lost the series to the Red Sox in seven games.

The Pirates struggled in the 1950s and early 1960s, but they rebounded in 1960 with one of the most memorable seasons in baseball history. The team won the National League pennant and faced the New York Yankees in the World Series. The series was a classic, with both teams winning three games apiece before Game 7 at Forbes Field in Pittsburgh. In the bottom of the ninth inning of Game 7, Bill Mazeroski hit a walk-off home run to give the Pirates a 10-9 victory and their fourth World Series championship.

The Pirates remained competitive throughout the 1960s and 1970s, thanks in large part to the contributions of players like Roberto Clemente, Willie Stargell, and Dave Parker. In 1971, the team won another World Series, defeating the Baltimore Orioles in seven games. The Pirates' victory in 1971 was notable for the performance of pitcher Steve Blass, who won two games in the series and was named the series MVP.

The Pirates continued to be a competitive team throughout the 1980s, thanks to the contributions of players like Barry Bonds, Bobby Bonilla, and Andy Van Slyke. In 1990, the team won the National League East division and faced the Cincinnati Reds in the National League Championship Series. The Pirates lost the series to the Reds in six games, but the team's success in 1990 marked the beginning of a new era of competitiveness for the franchise.