The Phillies have promoted assistant GM Ruben Amaro to their GM spot, replacing Pat Gillick. I'm not sure whether taking over a team that just won the World Series would be a great job or a horrible one. Director of scouting and player development Mike Arbuckle, who had been the other main candidate for the job, then informed the Phillies he was quitting.
I'm considering having a Best GM tournament--the inverse of the Worst GM tourney we did back in April--and one factor that has kept me from doing it is indecisiveness about whether Gillick should be included. Yes, he's retired now, but he would otherwise deserve consideration.
His career is remarkable--he worked for Houston back when they were still called the Colt '45s. After several years working in scouting and development, he hooked up with the expansion Toronto Blue Jays as an assistant GM, and was promoted to GM in 1978, one year after they took the field. He grabbed Willie Upshaw in the Rule 5 draft almost immediately (literally four days, if the estimation on Baseball America's Executive Database is right) after being hired, then got Lloyd Moseby and Dave Stieb in his first draft. (Upshaw, by the way, was plucked from the Yankees, for whom Gillick had worked as director of scouting in 1975 and 1976; Upshaw was Gillick's best draft pick for New York.)
He then took five years to build Toronto's first winning team, led by Stieb and a good offense featuring Moseby, Upshaw, the inherited Jesse Barfield and Ernie Whitt, and a pair of hitters in Rance Mullinks and Cliff Johnson who Gillick picked up in shrewd trades. After that, Toronto reeled off eleven consecutive winning seasons, all on Gillick's watch, including five division titles and two World Series titles.
Gillick retired after 1994, then took the Orioles' GM job after the 1995 season. Gillick's three seasons with Baltimore were not his finest. The Orioles won under Gillick, but that was mostly the result of a strong core of players he inherited, and he acquired several players just as their careers were about to go belly-up (Doug Drabek, Geronimo Berroa, Norm Charlton). The '97 Orioles were notable for their lack of obvious weaknesses, which is one mark of a well-built team, but the '98 O's were mediocre. Gillick retired after the season, and the Orioles haven't had a winning record since. Most of that has to do with terrible mismanagement since he left, but his trio of weak drafts for Baltimore didn't help.
Gillick took over the Mariners in 2000. By this point, he'd established a pattern of great timing, if nothing else--he'd left the Jays and Orioles just as the winning was about to stop--and his timing with Seattle was great, too. He inherited a fantastic core of talent, and the Mariners won 91 or more games during all of Gillick's four seasons in charge. They also won a spectacular 116 games in 2001. Gillick deserves part of the credit for that--he signed Bret Boone before the season and got a mega-breakout from him, and Ichiro Suzuki, bought from Orix in Japan before the season, really was the sparkplug that most fans imagine their speedy outfielders to be.
Gillick's two seasons spent as "special consultant" to Bill Bavasi after Gillick stepped down as GM were terrible, in that, yet again, Gillick got away just before the explosion (the Mariners were awful in 2004 and 2005), and in that it was never completely clear who was making the dubious trades and signings that contributed to the Mariners' decline.
Gillick took the Phillies' GM job after the 2005 season and immediately resolved a first base logjam that had flummoxed his hapless predecessor Ed Wade, trading Jim Thome to the White Sox. Ryan Howard promptly rewarded the Phillies by hitting 58 homers in 2006. Gillick yet again inherited a good core of talent (Wade and his underlings actually weren't bad at acquiring talent, they just had no idea what to do with it) and his time with the Phillies had its share of frustrations (like the parade of bad third basemen and the team's refusal to recognize that Brett Myers would be most helpful to them as a starter), but it's hard to argue with a World Series title.
Gillick wasn't a perfect GM. His best skill really was his timing. His drafting record wasn't very good, that first year with the Jays aside, and he would probably have been a very bad GM for a small-payroll team. He also frustrated fans in Seattle by refusing to acquire players at the trade deadline who would've helped the Mariners win a World Series. But he ended up winning three titles in the course of his career anyway, and his performance with the Jays was hard to argue with.