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.

Not many GMs have had a career arc like Dan Duquette. Despite undeniable success in Montreal and Boston, he spent what would ordinarily be the prime of his career (ages 43-53) unemployed, or at least not employed by a Major League team. The Orioles gave him another shot after at least one other candidate had turned them down, but it should have surprised no one when he had success right away in Baltimore.

Duquette played baseball at Amherst before getting hired by fellow alum Harry Dalton as a Milwaukee scout in 1981. By 1987 he was the player personnel director for the Expos, and during his tenure the club drafted or signed Vladimir Guerrero, Javier Vazquez, Orlando Cabrera, Delino DeShields, Marquis Grissom, Cliff Floyd and Rondell White. After the 1991 season Montreal GM Dave Dombrowski left to run the expansion Marlins, and the 33-year-old Duquette took over the Expos, a last place team filled with young talent, mainly players he had helped bring into the organization.

It did not take Duquette long to make his mark. Within three years he had traded for pitchers Ken Hill, John Wetteland, and Pedro Martinez. Just a few weeks into the 1992 season he replaced embattled manager Tim Runnels with Felipe Alou, 57-years-old and languishing in the system. Alou was perfect for the young team — which now included all of the aforementioned youngsters plus Moises Alou (Felipe’s son) and Larry Walker. The team won 87 games in 1992, then 94 in 1993, just three games behind the Phillies.

In January 1994 Duquette was lured away to run the Boston Red Sox. (The team Duquette left behind in Montreal would have the game’s best record in 1994 when a player strike ended the season in August.) As a Massachusetts native, Boston was Duquette’s dream job, and the club also gave him a bigger budget and a higher salary. The Red Sox had finished seventh and fifth the previous two years.

As an early adopter of using advanced statistics to identify players, he was known for acquiring undervalued players and getting production from them — Troy O’Leary, Brian Daubach, Jeff Frye, Tim Wakefield. He also tended to look for offense-valued players while tolerating their sub-par defense — Jose Canseco, Will Cordero, Kevin Mitchell, Jose Offerman, Carl Everett — with mixed results. His 1995 team included a few stars he inherited (Roger Clemens, Mo Vaughn, John Valentin) and a lot of his own shrewd pickups. The Red Sox won the division by seven games.

Both Clemens and Vaughn left as free agents, but more stars soon took their place. Nomar Garciaparra joined the lineup in 1997, and later that year Duquette made two of the greatest trades in team history. In July he dealt mediocre reliever Heathcliff Slocumb to the Mariners for pitcher Derek Lowe and catcher Jason Varitek. After the season he dealt two minor league pitchers for a 26-year-old Pedro Martinez. Lowe and Varitek would have long careers with occasional stardom, while Martinez and Garciappara would be among the game’s best players for the next several years.

Beginning in 1998, the Red Sox finished second (always to the Yankees) for eight straight seasons. They captured the wild card in 1998 and 1999, losing the ALCS to New York in the latter season. At this point in his tenure team ownership clearly instructed Duquette to spend the money and go for the brass ring. After falling back in 2000, Duquette signed Manny Ramirez, the biggest free agent on his resume. A year later he signed Johnny Damon, giving the Red Sox (with Trot Nixon) one of the game’s best outfields.

In early 2002 a group headed by John Henry purchased the Red Sox, and Duquette was fired soon after. Despite his track record, his reputation with the press and fans had soured. He was blamed for losing Clemens, whose late career resurgence was a constant reminder, and Vaughn. He hired a statistical consultant whose bizarre behavior and public comments did the analytical revolution no good. He was accused of making rapid-fire deals like a Rotisserie League GM, without regard for clubhouse harmony or stability. And his 2001 late season promotion of pitching coach Joe Kerrigan as manager proved to be a disaster for all concerned. Duquette did himself no favors with his shy demeanor, which some considered aloof or arrogant. The new owners decided on a fresh start, letting both Kerrigan and Duquette go.

Duquette next endured his ten years in the wilderness. His name often surfaced when GM openings arose, but he stayed out of the big leagues, opening a sports academy in western Massachusetts and running a couple of summer collegiate teams. Finally, in November 2011 he became the GM of the Baltimore Orioles.

The once-proud Orioles had endured 14 straight losing seasons at the time of Duquette’s hiring but promptly won 93 games and a wild card playoff spot in his first season. This was mostly Andy MacPhail’s team, but Duquette deserves credit for cobbling together a good low-cost pitching staff, acquiring Miguel Gonzalez, Jason Hammel, and Wei-Yin Chen before the season. In 2013 the Orioles, largely unchanged, won 85 games and finished third.

The 2014 Orioles had to endure injuries to Manny Machado and Matt Wieters, and the drug suspension of Chris Davis, but Duquette and manager Buck Showalter brought the team in with 96 wins and a division title before losing the ALCS to the Royals. Key additions to this club included Nelson Cruz (a league-leading 40 home runs), Steve Pearce (an OPS+ of 160 in 93 games) and pitcher Bud Norris (15-8, 3.65). At the trading deadline Duquette picked up reliever Andrew Miller, who posted a 1.35 ERA in 23 games down the stretch. For his efforts, Duquette was named Executive of the Year, 22 years after winning the award with Montreal.

As of this writing there are reports that Duquette could be headed to Toronto to become CEO. If so, this might put an end to an impressive general managerial career, with undeniable success improving three franchises over 14 years.

— Mark

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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.