Tim Wakefield had one of the most fascinating pitching careers in the modern Major Leagues. He was a phenom with the Pittsburgh Pirates as a rookie in 1992, leading the team to the postseason and becoming a star. But he lost himself in 1993, and after a players’ strike and another disappointing season with the Pirates he was off the team.
But Wakefield rebuilt his career as a knuckleballer, catching on with the Boston Red Sox for 17 seasons in which he pitched the most innings in Red Sox history. He won 200 games, two World Series, and pitched as baseball experienced a steroid era and a statistical revolution. Wake gave up the game-losing home run to Aaron Boone in Game 7 of the 2003 ALCS, only to pitch crucial innings the next season as the Red Sox won their first World Series in 86 years.
Today, Wakefield is the honorary chairman of the Red Sox Foundation. He talked to Uproxx about his career on the mound, the impact winning has on a franchise, and what the future holds for America’s Pastime while working with Subway to rebuild a Little League baseball field in New England.