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This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post. Pat Gillick served as a general manager for four different teams. At his first stop, in Toronto, he built an expansion team into one of the best organizations in the game (winning 86 or more games for 11 straight seasons), culminating in five division titles and two world championships. In Baltimore, he worked for an impatient owner who wanted his team to compete right away — Gillick delivered two consecutive ALCS appearances, the Orioles only post-seasons between 1983 and 2012. In Seattle, he was tasked with trading one of the game’s best players, and then watching another superstar leave as a free agent a year later. Despite this, his Mariner teams won over 90 games all four of his years at the helm and an all-time record win total 2001. At his final stop, in Philadelphia, he took over a good team that had not been able to get over the hump and into the playoffs. Gillick made the post-season in his second year and then won the World Series in 2008, the team’s first in 28 years. A few days later, he retired. By succeeding at four distinct challenges without fail and showing a unique ability and keenness for finding talent others might have overlooked, Gillick earned a place among the very best GMs in history. Gillick’s approach was to first make sure he had great scouts and then to widen his talent search to non-traditional avenues. As Gillick put it: “One needs to fish in many waters.” In Toronto Gillick and his longtime friend Epy Guerrero were at the forefront of creating an identifiable presence in the Dominican Republic. He also looked for underappreciated opportunities with multi-sport athletes. His success in the mostly ignored Rule 5 draft of veteran minor leaguers was legendary; no one else even came close to his success and he forced teams to be much smarter about protecting their assets from this draft. Moreover, Gillick used free agency to perfection in Baltimore and Seattle—in both places he quickly reloaded franchises with little talent left in their minor league systems. With the latter organization, he also signed the first hitter from Japan to star in the major leagues, Ichiro Suzuki, along with a first-rate reliever, Kaz Sasaki. Toronto’s head of baseball operations Peter Bavasi brought Gillick—who had been gaining a reputation as a front office savant with the Yankees –over to help build the expansion Blue Jays for their inaugural 1977 season. The next year Bavasi moved up to team president, and Gillick took over as GM. With the Blue Jays he immediately set about building a top-notch scouting staff. Two of his most important hires were Al LaMacchia, a longtime scout for the Phillies and Braves, and Bobby Mattick, who had already signed Frank Robinson, Vada Pinson, Curt Flood, and Gary Carter by the time he joined the Blue Jays. Both became important voices within the organization. He joined a minority of teams that shunned the new centralized Major League Scouting Bureau. Gillick was going to assemble his own organization. Along with slowly building up talent throughout the draft, Gillick looked for other avenues to find players. In the fall of 1977 Gillick began to exploit a little-used “river” when he selected first baseman Willie Upshaw, whom he and Guerrero knew from the Yankees organization, in the Rule 5 draft. This draft allows teams to claim veteran minor leaguers not protected on their club’s 40-man roster, but with the qualification that the selecting team had to keep the player on its major league roster for the entire upcoming season. Over the years Gillick mastered the Rule 5 draft to uncover a number of other valuable contributors, including George Bell, Manny Lee, Jim Gott, and Kelly Gruber. Gillick was also willing to take risks with multi-sport athletes, accommodating them in ways other teams might not have. In 1977 Gillick drafted multi-sport prep star Danny Ainge in the fifteenth round. Two years later he drafted prep quarterback and baseball catcher Jay Schroeder in the first round, paying a $100,000 bonus and allowing him to play college football at UCLA. In the end, neither panned out but testified to Gillick’s never ending quest for an edge in talent acquisition. Gillick had known Epy Guerrero, destined to become the Dominican Republic’s greatest scout, at least since 1967 when Gillick was a scout for the Astros and the two signed Cesar Cedeno. In 1977 Guerrero created a rudimentary baseball school for youngsters. Several years later the Blue Jays began to fund the operation, expand it, and run it year round, establishing a prominent presence in the country, one that provided the team an advantage for a decade or more. In 1983 the Blue Jays finally passed .500, winning 89 games. Two years later they won 99, but lost a heartbreaking ALCS to the Royals. The team continued to win as Gillick integrated a number of young stars–Bell, Tony Fernandez, Tom Henke, Fred McGriff, Duane Ward, John Olerud, David Wells, and Pat Borders—and dealt for Robbie Alomar and Devon White but could not quite capture the pennant. But Gillick still had one more river to fish in. With the opening of Skydome and the associated increase in revenues, he could focus on high-level free agents to augment the club. It would take him one more year, but Pat Gillick would prove a master of this strategy. Gillick also self-imposed a three-year contract limit to prevent getting stuck with aging stars in a long decline phase. In the 1991-92 offseason Gillick signed 37-year-old Twins pitcher Jack Morris and aging Angels’ slugger Dave Winfield, and the Blue Jays won the World Series. After the 1992 season, Gillick was faced with seven key Blue Jays becoming free agents: Henke, Winfield, Jimmy Key, David Cone, Joe Carter, Manny Lee, and Candy Maldonado. Of the seven, Gillick re-signed only Carter, but added veterans Dave Stewart to bolster the pitching staff and Paul Molitor to replace Winfield at DH. Once again, Toronto won the World Series. After the strike-shortened 1994 season Gillick stepped aside due to some health concerns and simply tiring out after so many years in one place. A year later he jumped back in as Baltimore’s GM. The team had dropped below .500 in 1995, and owner Peter Angelos wanted to reach the postseason. Gillick went to work. He diagnosed the Orioles biggest deficiencies at second and third base and the bullpen, and the farm system did not offer much immediate help. Gillick filled these holes quickly and effectively, while still holding to the three-year contract limit he had used in Toronto. He signed free agents Robbie Alomar, his old Toronto standout, to play second, and B.J. Surhoff to play third. To shore up the bullpen, he signed Randy Myers and Roger McDowell. Finally, to make up for the loss of departing free agent hurler Kevin Brown, Gillick traded young outfielder Curtis Goodwin for David Wells, another ex-Blue Jay. The team won the wild card and made it to the ALCS. In 1997 Baltimore won the East with the AL’s best record and again made it to the ALCS before falling to the Indians in a heartbreaking series. Gillick left Baltimore after the 1998 season (his friend and manager Davey Johnson had left a year earlier). Once again Gillick returned to the game after a year off, this time with the Seattle Mariners. With the opening of their new stadium a year earlier, Seattle’s ownership wanted a championship-quality ball club. Coming off of two sub-.500 seasons, however, a drained farm system and with two of baseball’s biggest stars—Alex Rodriguez and Ken Griffey Jr—scheduled to become free agents one year later, Gillick had his work cut out for him. That they could keep neither (though Gillick did get Mike Cameron included with a package of players in trade for Griffey) meant Gillick needed find players outside the system. Gillick succeeded spectacularly and quickly, transforming the 79-win 1999 team into one that went to the ALCS in 2000 and won an AL record 116 games in 2001. He turned over nearly the entire squad, masterfully using free agency. Among the key players, John Olerud, Bret Boone, Mark McLemore, Stan Javier, Aaron Sele, Jeff Nelson, Arthur Rhodes, Kazuhiro Sasaki, and Ichiro Suzuki were all signed as free agents in just two off-seasons. Moreover, the final two players in the list came from Japan, a new river for Gillick to fish in, and Ichiro became the first Japanese non-pitcher to excel in the U.S. major leagues. Though Gillick had wanted to restock the farm system during his years in Seattle, that goal was secondary to delivering a title. He was hampered by the loss of draft choices from all his free agent signings, another pitfall of relying heavily on a free agency. In fact, the Mariners had only one first round draft choice during his four years at the helm and failed to sign him (John Mayberry Jr.). Gillick’s scouts, however, remained active internationally, and the team signed four impact players for the minor league system during Gillick’s tenure: Shin-Soo Choo, Jose Lopez, Felix Hernandez and Asdrubal Cabrera. After a couple of years out of baseball, Gillick, now 68, took over as the GM in Philadelphia. In contrast to his three previous stops, the Phillies team he took over was filled with young talent, including Ryan Howard, Jimmy Rollins, Chase Utley, Brett Myers, and Cole Hamels. Over the next couple of years Gillick bolstered his young nucleus with a couple of veteran hurlers, including former Mariner Jamie Moyer, an excellent bullpen, and Jayson Werth. Moreover, he managed to do this without surrendering any of his key players–the core he inherited in 2005 was all on hand to celebrate the World Series victory in 2008. With his three-year contract up and his third world championship earned, Gillick decided it was time to retire. He was 71 years old and had succeeded with a fourth organization, a remarkable feat unmatched by any other GM, fully validating his credentials as a master team builder. Gillick’s obsessive search for the best players, wherever they may have been, allowed him to thrive in the face of diverse challenges. To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.