He might be forgiven if he can orchestrate a similar feat in Philadelphia. To that end, the veteran baseball executive became the third to interview for the vacant general manager's job. He followed assistant GM Mike Arbuckle and former Houston GM Gerry Hunsicker, who met with team president David Montgomery on Wednesday and Thursday, respectively.
"It's a very good situation to be in," said Gillick. "I've known [Montgomery] for years, socially, although we never sat down and talked baseball. I know Dallas Green and Mike Arbuckle and Ruben Amaro Jr. I know most of the players through being in the American League or scouting."
Gillick also knows that he wants to be a GM for the fourth time, though this would be his first National League post. He's had success at every stop, as his teams in Toronto, Baltimore and Seattle have a 2010-1773 record, seven division titles and two World Series championships.
"I still have the passion and want the competitve edge," he said. "As long as I still feel that way, I would like to get back at that level and the Phillies is a good opportunity. There is a great foundation."
"He's accomplished a great deal as a GM in three different situations," said Montgomery, breaking a two-week silence to update reporters. "Clearly, he's had enormous success in Toronto, then, although it was a brief period in Baltimore, he was in the postseason and he was able to do that again in Seattle."
Montgomery also raved about Hunsicker, who assembled five playoff teams during his 10 seasons as general manager. He served in an advisory role last season, and the Astros advanced to their first World Series.
In his state-of-the-GM-search address, Montgomery said more than 40 candidates have either been contacted or expressed an interest in the job, directly or indirectly. From that list, Montgomery and top advisors Green and John Vukovich selected candidates, who have met or will meet with Montgomery for one-on-one interviews.
Amaro Jr. gets his chance over the weekend. He and Arbuckle are the only in-house candidates being considered, though both appear to be longshots. Others will meet next week, though Montgomery declined to name them until after the interview. He set no timetable on a final decision.
"I fully expect this process to continue through the weekend and next week with the hope of identifying our next GM as soon as possible," Montgomery said.
If no one is named by Nov. 11, when the annual general manager's meetings start in Indian Wells, Calif., Montgomery will go with Amaro, Arbuckle and Major League scout Gordon Lakey. Other matters, such as negotiations with Billy Wagner and potential trades, will continue to be handled by Amaro.
"I'd like to get the right person as soon as possible," Montgomery said. "I'm trying to get away from a rigid timetable. I'm aware that GM meetings are coming up. There are, probably, desired intervals along the way. At that same time, the most important thing is to make the best possible decision."
Montgomery added that second interviews won't be required in all cases. Timing might also become an issue when it comes to Hunsicker, who has met twice with the Devil Rays.
But finding the right GM is paramount.
"The goal is to find one person to be in charge of our entire baseball operations," Montgomery said. "That's where our focus has been. What I've tried to do in reviewing people is to see if I couldn't identify a list of people who are somewhat varied in background, and perhaps the process itself would help us identify not only the specific candidate but also the best candidate who would fit our situation."