Front Office Career
Gillick retired from playing and began a front-office career in 1963, when he became the assistant farm director with the Houston Astros. He would eventually work his way up to the position of Director of Scouting before moving to the New York Yankees system in 1974, as a Coordinator of Player Development. In 1976, he moved again, this time to the expansion Toronto Blue Jays, becoming their Vice President of Player Personnel, and in 1977, their Vice President of Baseball Operations and General Manager. In 1984, he was named Executive Vice President of Baseball Operations.
As Toronto's general manager, Gillick won five division titles (1985, 1989, 1991, 1992 and 1993) and led the club to their first World Series championships in 1992 and 1993. Shortly after Gillick left, the Blue Jays went into decline, not finishing higher than third place until the 2006 season.
In 1995, Gillick was named the general manager of the Baltimore Orioles to replace Roland Hemond, who had resigned. He cited the fact that they were close to winning a championship as a factor to his decision to come out of retirement. He guided the Orioles to the playoffs in 1996 and 1997. He resigned at the conclusion of his three-year contract in 1998. The Orioles struggled shortly after his departure, failing to achieve a winning season until 2012.
Gillick then became the general manager of the Seattle Mariners, who had parlayed their incredible 1995 playoff run into a new ballpark and the financial resources to become a perennial contender. Upon his hiring, the responsibility fell on Gillick to trade Ken Griffey, Jr. to Cincinnati after Griffey played out his final season in Seattle. The Mariners made back-to-back playoff appearances for the only time in franchise history in 2000 and 2001, and the 2001 team, with a 116–46 record, tied the 1906 Chicago Cubs for the all-time Major League Baseball record for most wins in a single season. However, the Mariners failed to make it past the American League Championship Series in either year, and did not make the playoffs for the rest of Gillick's tenure as GM and advisor.
Like the Blue Jays, the Mariners have also not reached the playoffs since his departure as GM.
Gillick was inducted into the Toronto Blue Jays "Level of Excellence" on August 8, 2002.
On November 2, 2005, Gillick was named the Philadelphia Phillies' general manager. Gillick's first big move in Philadelphia was to trade Jim Thome and cash to the Chicago White Sox for Aaron Rowand and prospects Gio Gonzalez and Daniel Haigwood.
In June 2006, Gillick faced criticism from members of the media and women's groups for allowing pitcher Brett Myers to make his scheduled start against the Boston Red Sox on June 24, 2006, just one day after being arrested for assaulting his wife on a Boston street. Gillick was quoted by The New York Times as saying "I think it's in the best interest of the club; he's our best pitcher".
Gillick had permanent residence in Toronto with his wife Doris, but they have since re-located to Seattle after he became the Phillies GM. He became a Canadian citizen in 2004.
Gillick retired as a GM after leading the Phillies to a World Series championship in 2008. Assistant general manager Rubén Amaro, Jr. was named his successor. Although he retired from all general manager duties, Gillick remains in the organization as a senior advisor to Amaro and Phillies president David Montgomery.
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