MacPhail began his career as a baseball executive with the
Chicago Cubs'
Rookie-level Minor League Baseball affiliate in 1976. After a year in the role, he became an assistant in the Cubs' parks operations department, and was promoted to assistant director of player development. He joined the front office of the
Houston Astros of
Major League Baseball as their assistant director of scouting in 1981, and then was promoted to assistant to the
general manager in 1982. He was hired as the
Minnesota Twins' vice president of player development in 1984, Under MacPhail, the Twins won the
1987 World Series and
1991 World Series championships. The 1991 Twins rebounded from a last place finish after MacPhail signed
Jack Morris in the offseason. MacPhail demoted
Larry Himes, the Cubs' general manager, and hired
Ed Lynch to fill the role. The Cubs reached the playoffs when they won the
National League wild card spot in 1998. They won the
National League Central division in 2003.
Peter Angelos, the owner of the
Baltimore Orioles, hired MacPhail as the team's
president of baseball operations on June 20, 2007. Before the 2008 season, MacPhail traded
Érik Bédard for a package that included
Adam Jones and
Chris Tillman. He acquired
J. J. Hardy after the 2010 season and
Chris Davis and
Tommy Hunter at the trade deadline in 2011. He also hired
Buck Showalter as manager during the 2010 season. Many of the players acquired by MacPhail, as well as Showalter, helped the Orioles reach the postseason after MacPhail's departure. On June 29, 2015, the
Philadelphia Phillies hired MacPhail as a special assistant to
Pat Gillick, the team's president. MacPhail succeeded Gillick as president at the end of the 2015 season. On December 11, 2020, he was succeeded by
David Dombrowski. ==Personal==