3. Mike Boddicker for Brady Anderson and Curt Schilling

In a 1988 deadline deal, the Orioles sent Boddicker, a solid starting pitcher who was a Cy Young candidate in 1984, to the Red Sox for Anderson and Schilling. Anderson became a mainstay in center field at Camden Yards and hit a franchise-record 50 homers in 1996. This trade could have been the Orioles' best had they not traded Schilling, one of the most clutch pitchers in playoff history, in the 1991 deal for Glenn Davis.

( Baltimore Sun )

In a 1988 deadline deal, the Orioles sent Boddicker, a solid starting pitcher who was a Cy Young candidate in 1984, to the Red Sox for Anderson and Schilling. Anderson became a mainstay in center field at Camden Yards and hit a franchise-record 50 homers in 1996. This trade could have been the Orioles' best had they not traded Schilling, one of the most clutch pitchers in playoff history, in the 1991 deal for Glenn Davis.

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