This post is part of a series in which we count down the 25 best GMs in history. For an explanation, please see this post.

Andy MacPhail had big shoes to fill. Both his father Lee and his grandfather Larry are in the Hall of Fame as baseball executives. When the Minnesota Twins promoted the 33-year-old MacPhail to run the club, they surely took his pedigree into account. He lived up to his surname, and his surprisingly quick success cemented a wave of extremely young GMs, a couple with similar front office bloodlines.

Coming out of college in 1976 MacPhail knew he wanted a career in a baseball front office and thought he had lined up a position with the Montreal Expos. Unfortunately, when the American League awarded an expansion franchise to Toronto that spring, creating a second major league team in Canada, the Expos were so dismayed with American League president Lee MacPhail that they rescinded the employment offer to Lee’s son. Andy quickly rebounded, taking a positon with the Cubs in park operations and player development. In early 1982, just 28, he joined Houston as assistant to general manager Al Rosen.

New Minnesota Twins owner Carl Pohlad brought in MacPhail as vice president of player personnel in 1985 and one year later made him general manager, at 33 the youngest GM in baseball. The Twins had been mired in mediocrity or worse for the previous decade and a half; nevertheless the squad MacPhail took over had a number of talented young homegrown players, including Kirby Puckett, Kent Hrbek, Gary Gaetti, and Frank Viola.

MacPhail made several moves to bolster his nucleus with veteran talent, trading for left fielder Dan Gladden and closer Jeff Reardon and signing reliever Juan Berenguer. The 1987 Twins crept up to 85 wins, but it was enough to win a weak AL West and beat the Tigers in the ALCS. When the Twins defeated the Cardinals in the 1987 World Series, everyone associated with the team became a regional hero, perhaps because other than the Minneapolis Lakers in the late 1940s and early 1950s (before the NBA was popularly established as a national league), no Minnesota professional team had won a championship in any of the four major sports. MacPhail was hailed as “Boy Wonder.”

Despite his quick success, MacPhail recognized that lower revenue teams could only compete cyclically and that a team needed a solid crop of low-salaried youngsters and under-appreciated veterans who could ripen concurrently, leaving some payroll available to plug holes with free agents. Sensing the team was not ready to compete for a title, in 1989 MacPhail traded Viola, the previous year’s Cy Young Award Winner, for several players, most notably pitchers Rick Aguilera and Kevin Tapani. The Twins fell to last place in 1990, but MacPhail felt his restructured team had enough talent and some payroll flexibility.

Before the 1991 season he signed free agents Mike Pagliarulo, Jack Morris, and Chili Davis, while farm products Chuck Knoblauch and Scott Erickson came through with star-quality seasons. The team won 95 games, going from last to first in their division, and again prevailed in a seven game World Series. More than two decades later, these two Twins World Series victories remain Minnesota’s only substantive men’s professional sports championships. During his stint in Minnesota MacPhail was brilliant at managing his payroll, recognizing when he had a team close to contention, and using his payroll capacity to acquire in the right veterans.

MacPhail’s success helped usher in a new era of very young GMs. Oakland had hired Sandy Alderson in 1983, and Texas had brought in Tom Grieve a year later—both just 35—but after MacPhail the minimum age fell even further. Dave Dombrowski and Jim Bowden were only 31 and Randy Smith just 29 when hired. Smith and Bill Bavasi, just 36 when he became a GM, were like MacPhail scions of successful front office executives. Somewhat surprisingly, other than by Alderson, the analytic revolution that was slowly seeping into baseball before Moneyball was not really embraced by this generation of young GMs.

The Twins remained competitive in 1992, but fell off quickly thereafter as several players left as free agents, the pitching deteriorated, and several younger players performed below expectations. With rapidly increasing salaries throughout baseball after an arbitrator ruled the owners had been colluding to keep salaries down, MacPhail was becoming increasingly pessimistic on the future of small market clubs. “I can’t make it work anymore,” MacPhail said regarding even his successful cyclic approach to building a competitive team.

After a players strike shut down the final phase of the 1994 baseball season, the Tribune Company hired MacPhail to be president and CEO of the Cubs, one of baseball’s most venerable but long-suffering teams. As his title implied, MacPhail was responsible for the entire franchise and named Ed Lynch his general manager. MacPhail intended to build a “development-based” organization while at the same time bringing in veterans to keep Chicago competitive in a weak division.

In mid-2000, after just one playoff appearance in five years, MacPhail jettisoned Lynch and assumed the GM duties himself. He got the club up to 88 wins in 2001, but the next July MacPhail named Jim Hendry the GM. In 2003 the Cubs won 88 games and qualified for the playoffs, where the team advanced to the NLCS, before losing a heartbreaking seven game series to the Marlins. The Cubs would not make the post season again under MacPhail’s reign, and he resigned after a disappointing 66-96 record in 2006. Certainly the Cubs suffered some bad luck—phenom pitchers Kerry Wood and Mark Prior pitched 200 or more innings only three times between them due to injuries–but the farm system did not deliver as expected and several prospects were traded away with little substantive return. In contrast, MacPhail was highly successful in the off-field part of his job, as attendance and revenues surged during his 12 years at the helm.

MacPhail was not unemployed for long; in mid-2007 Orioles owner Peter Angelos brought him aboard as president of baseball operations, acting as a general manager with considerable authority. Baltimore had fallen on hard times since consecutive ALCS trips in the late 1990s, winning fewer than 80 games every year from 1998 to 2007, but MacPhail again hoped to create a “top echelon scouting and development franchise.” When the farm system appeared to be more efficient at developing pitching, MacPhail’s strategy evolved to “buy the bats and grow the arms.”

Unfortunately, many of the young hurlers never progressed as hoped, and the Orioles lost over 90 games every season through 2011, after which MacPhail resigned. The next year Baltimore was baseball’s surprise team; they won 93 games and made the playoffs, mostly with a team built by MacPhail. Although he wasn’t around to enjoy it, MacPhail’s farm system and savvy trades for the likes of Adam Jones, Mark Reynolds, J.J. Hardy, and Chris Davis left the Orioles with a solid talent base.

— Dan

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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.