Gillick has spent nearly 50 years in the Major Leagues, including time with six different organizations. When it was time to reflect on his much celebrated career, though, it was the city of Toronto that was mentioned time and time again.
His favorite season in the Majors? 1985, when the Blue Jays made the playoffs for the first time in franchise history. His favorite trade? Acquiring Joe Carter and Roberto Alomar from the San Diego Padres for Fred McGriff and Tony Fernandez. Gillick even said the low point of his career happened in Toronto when the Blue Jays blew a 3 1/2-game lead in the final week of the 1987 season to miss the playoffs.
That's not the year Blue Jays fans will remember the most, though. Instead, they'll fondly look back on Gillick for building an organization from the ground up and creating what is still remembered as the glory days of baseball in the city.
Gillick joined the organization in 1976 and was tasked with building the club through the Expansion Draft. All of his hard work culminated nine years later, when the club made the playoffs for the first time.
"People asked how you felt -- it felt like you got to the top of the hill," Gillick said of the Blue Jays' playoff run. "You were climbing the whole time, and finally, you got there. I think probably that was the most satisfying season. Just the fact that we worked so hard from '77 in the Expansion Draft.  was the one where you kind of said, 'Wow we kind of made it to the top.'"
Gillick becomes the 32nd executive to gain entry into the Hall of Fame and just the fourth to be elected almost solely on his work in the front office -- joining Ed Barrow, Branch Rickey and George Weiss.
The native of California helped put the Blue Jays on the map by focusing on player development in Latin America. He teamed up with scout Epy Guerrero to sign the likes of Damaso Garcia and Tony Fernandez. He targeted other Dominican players such as former American League MVP George Bell through the Rule 5 Draft.
Gillick said it was all part of a strategy to make baseball in Toronto relevant.
"We felt the only way we were going to become competitive, especially [when] we weren't very attractive to free agents going to Canada, that we were going to have to develop the players ourselves," Gillick said.
"That was part of our game plan, to develop those players in Latin America and add to the players we were trying to develop at the same time from the United States."
For awhile, Gillick's patience earned him the nickname of "Stand Pat" in Toronto for his reluctance to make big moves. He shed that title on Dec. 5, 1990 -- exactly 20 years before the Hall of Fame vote was conducted -- when he traded cornerstones McGriff and Fernandez to San Diego for Carter and Alomar.
The deal would prove to be one of the final pieces required for what would turn into back-to-back World Series titles in Toronto during 1992-93.
"That was a good trade for both clubs," Gillick said. "We needed a right-handed hitter, and they wanted to make a move and get a left-handed hitter for first base in McGriff.
"But looking back, that was one of the best trades from the standpoint that everybody came out a winner. It was a winning trade for both of us, but probably more so for the Blue Jays, because Joe and Robbie contributed so much in '92-93."
Gillick now has the possibility of being honored alongside Alomar at the Hall of Fame induction weekend July 22-25. Alomar is considered a front-runner to be elected into the Hall during the Baseball Writers' Association of America voting on Jan. 5, 2011.
"I think it would be tremendous," Gillick said of Alomar joining him in the Hall. "I think he is well deserving -- he's the best second baseman I've seen all around, both defensively and offensively, probably in the last 20 years. It would be a thrill if he did make it and we could both go in at the same time."
In fact, Cooperstown could be overrun that weekend by people associated with Toronto. In addition to Alomar, Toronto Sun baseball columnist Bob Elliott is a finalist for the Spink Award for writing and the late Tom Cheek is a finalist for the Frick Award for broadcasting.