He has previously served as general manager for the Minnesota Twins and Chicago Cubs, and as president for the Baltimore Orioles and Philadelphia Phillies.

[4] MacPhail demoted Larry Himes, the Cubs' general manager,[1] and hired Ed Lynch to fill the role.

[7] Peter Angelos, the owner of the Baltimore Orioles, hired MacPhail as the team's president of baseball operations on June 20, 2007.

[3] Before the 2008 season, MacPhail traded Érik Bédard for a package that included Adam Jones and Chris Tillman.

[6] On June 29, 2015, the Philadelphia Phillies hired MacPhail as a special assistant to Pat Gillick, the team's president.

[11] MacPhail graduated with a degree in American studies from Dickinson College in Carlisle, Pennsylvania, in 1977,[2] where he was a member of Kappa Sigma fraternity.