Arizona Diamondbacks — Max Scherzer
Trade Details: Max Scherzer and Daniel Schlereth to Detroit for Edwin Jackson and Ian Kennedy in three-team deal
The Diamondbacks have made a handful of head-scratching trades since entering the league in 1998. Following the 2003 season — just two years removed from winning the World Series — Arizona shipped Curt Schilling to Boston. In his first year with the Red Sox, Schilling went 21-6, finished second for the Cy Young, and led Boston to a World Series triumph.
Six years after trading Schilling, Arizona gave up on Max Scherzer and shipped the flamethrower to Detroit. While Ian Kennedy went on to go 21-4 in 2011, he never approached Scherzer’s level. Mad Max won his first Cy Young in ’13, won back-to-back CY’s in ’16 and ’17, and is regarded as one of the two-best pitchers of his generation (alongside Clayton Kershaw).