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.

After the 1996 season Florida Marlins owner Wayne Huizinga—angling for a new publicly financed stadium–asked general manager Dave Dombrowski what it would take to produce a winner the following season. Dombrowski didn’t prevaricate. He told his boss that he would deliver if allowed to take the payroll from around $31 million (in the lower third of the league) to roughly $44.5 million (near the top). Huizinga told him to go for it, and Dombrowski went to work, pulling the levers masterfully. In the end he overspent his projection by a couple of million but brought South Florida a World Series champion in only their fifth season of major league baseball. Once in a while you really can deliver on demand.

When he first took over the Expos in mid-1988, the 31-year-old Dombrowski was the youngest GM in baseball. Three years later he moved on to Florida where he assembled the World Series champion before salvaging a respectable return when forced to dismantle it. Finally, in Detroit, his third and current GM job, he rebuilt a struggling franchise, delivering two pennants and a recent string of division titles. Overall, Dombrowski’s won-loss record as a GM is less than stellar because he spent much of his time building up from the bottom. But at his two stops of any length, Dombrowski turned hapless franchises into winners with staying power—though only in Detroit was he allowed to execute on his longer term plans.

When Dombrowski told his eighth grade teacher as part of a student survey that he wanted to be a big league GM, she told him, “I can’t put that down. Nobody wants to do that.” But Dombrowski was persistent. His college thesis at Western Michigan was titled “The General Manager: The Man in the Middle.” After graduation, White Sox GM Roland Hemond appreciated Dombrowski’s passion and brains and gave him a job. A decade later he was in charge of the Expos.

Immediately after taking over in July 1988 Dombrowski pulled the trigger on a couple of trades, showing that he would be aggressive despite, or possibly because of, his youth. The next year Charles Bronfman, the original Expos owner, was thinking of selling, but wanted one more crack at a championship. Accordingly, with the team in contention at mid-season, Dombrowski made a couple deals for veteran pitchers, one of which turned out regrettably when he included a young Randy Johnson in a deal for ace pitcher Mark Langston. The Expos finished 81- 81 for the third consecutive year and many of their best players, such as Langston, Hubie Brooks, Pascual Perez, and Bryn Smith, left as free agents. They also failed to sign their first round draft pick, catcher Charles Johnson.

Bolstered by three rookies in 1990—Marquis Grissom, Larry Walker, and Delino DeShields—Montreal overcame its free agent losses and jumped to 85 wins. Rule 5 pickup Bill Sampen led the team in victories; free agent pick up Oil Can Boyd started 31 games with a 2.93 ERA; and Dombrowski acquired Moises Alou in a midseason trade. For his efforts Dombrowski was named UPI baseball executive of the year. Unfortunately, the team dropped back to 71 wins in 1991, despite a similar lineup (though Dombrowski had swapped Tim Raines—past his dominant prime–for Ivan Calderon and Barry Jones before the season).

As the 1991 season dragged on, Dombrowski grew more frustrated with his financial constraints. In September he joined the expansion Florida Marlins to build an organization and team for the inaugural 1993 season. The Expos organization he left behind contained many of the players that would contribute on the 1994 squad that would have the best record in baseball. Drafted and signed amateurs during his three plus years at the helm included Rondell White, Ugueth Urbina, Chris Haney, Cliff Floyd, Mark Grudzielanek, Matt Stairs, and Kirk Rueter.

In Florida, Dombrowski set about building the club’s system, bringing in a bevy of veteran scouts from Montreal and elsewhere. With his first pick in the 1992 amateur draft Dombrowski again nabbed Charles Johnson, whom he drafted and lost in Montreal. At the expansion draft Dombrowski picked up a number of useful veterans to either play or trade: Brian Harvey, Trevor Hoffman, Carl Everett, Jeff Conine, Greg Hibbard, and Danny Jackson. Dombrowski also made a huge trade that first season, landing 24-year-old Gary Sheffield and also dealt for future closer Rob Nen.

By 1995 Dombrowski realized that the team’s pitching was not as far along as its hitting, so in December he signed two quality undervalued hurlers: Kevin Brown and Al Leiter. For 1996, he also introduced 19-year-old Columbian signee Edgar Renteria. Their fourth season was the Marlins most successful in team history (every year they had won more games than the year before). But Huizenga wanted to accelerate the process.

To put the Marlins over the top, Dombrowski bolstered his squad with three of the top free agents on the market, Alex Fernandez, Bobby Bonilla, and Moises Alou, and several key role players. He also hired manager Jim Leyland, who had recently resigned from the Pirates. The team qualified for the postseason as the NL wildcard and went on to win the World Series.

But Huizenga did not get the stadium he wanted, claimed to be losing money, and wanted out of baseball. He gave Dombrowski the opposite directive of the one he had given twelve months earlier: drastically reduce payroll to make the team more saleable. If the rise of the Marlins was steady and unrelenting, the fall was startlingly swift. By Thanksgiving, Dombrowski had traded Alou, Nen, Conine, and Devon White. By New Year’s Day, Brown, Dennis Cook, and Kurt Abbott were also ex-Marlins. The 1998 team, the defending World Champions, finished 54-108, one of the worst records of the expansion era.

After the team’s sale, Dombrowski began to rebuild the team’s talent level under new owner John Henry, though the team maintained one of baseball’s lowest payrolls. At the conclusion of the 2001 season, with the team’s future in doubt, Dombrowski moved on to the Detroit Tigers as team president. He left behind a nucleus that would become (or used as trade chips to build) the 2003 world championship club.

In 2001 the Tigers had finished below .500 for the eighth consecutive year, and owner Mike Ilitch wanted a strong hand in charge. In April 2002 Dombrowski assumed the GM mantle as well. He quickly realized that his rebuilding task was even more daunting than it appeared on the surface. The Tigers were burdened with a number of bad contracts with injured or non-productive players. At an ill-advised “private” venting in front of some season ticket holders, Dombrowski named Craig Paquette, Dean Palmer, Damion Easley, Matt Anderson, Danny Patterson, Bobby Higginson, and Steve Sparks. Basically untradeable, these seven players, under contract for roughly $40 million, accounted for a huge portion of the payroll. The 2002 team finished 55 – 106, with little payroll flexibility. Dombrowski had his work cut out for him.

The next season was even worse. The 2003 Tigers started 3-25 en route to 119 losses, one shy of the 1962 Mets all-time record. Once again, however, Dombrowski was slowly rebuilding his team at a steady pace, using many sources. And as in his early days in Florida, his owner would pay up for scouts and front office executives. Dombrowski also brought in Jim Leyland, his World Series manager in Florida, after the 2005 season. His rebuilding culminated in the 2006 pennant.

Nearly all the key 2006 players were acquired under Dombrowski’s reign. Fireballing hurlers John Verlander and Joel Zumaya and center fielder Curtis Granderson came from the draft; infielders Placido Polanco and Carlos Guillen were trade acquisitions; Ivan Rodriguez was signed as free agent in February 2004, as much to make a statement as for his abilities, and Magglio Ordonez was signed a year later, overpriced but useful nonetheless; Todd Jones was signed as a free agent for 2005, and Kenny Rogers for 2006; Chris Shelton was a Rule 5 draftee; and Nate Robertson and Jeremy Bonderman were both acquired as youngsters early in Dombrowski’s tenure as part of veteran for prospects deals.

When several players suffered injuries in 2007 the team fell back, and Dombrowski realized he needed to again retool his squad. In December he made a huge trade, sending top prospects to Florida for Miguel Cabrera and Dontrelle Willis. The latter was coming off of a Cy Young runner up season, but was never healthy or effective in Detroit. Cabrera, however, became one of the best players in the game. Dombrowski’s trade record for the next few years was uncanny—he always seemed to know when to trade prospects for veterans or vice-versa. Moreover, he once again needed to maneuver around large contracts with players who no longer justified them, such as Willis and Ordonez.

In late 2009 in a three-way swap he surrendered Curtis Granderson, but received Austin Jackson and Max Scherzer. Going back the other way, at mid-season in 2010 and 2011 he landed first Jhonny Peralta and then Doug Fister for prospects. In another great trade at mid-season in 2012 he landed Omar Infante and Anibal Sanchez for several more farm hands. Enough of the prospects Dombrowski didn’t trade, such as Alex Avila and Rick Porcello, developed into quality major leaguers, injecting some youth into the team.

Dombrowski also showed a knack for finding undervalued free agents and signing them for reasonable contracts, including Jose Valverde (before 2011), Victor Martinez (2011), Brad Penny (2011), and Torii Hunter (2013). After appearing to overpay for Prince Fielder, Dombrowski swapped him for Ian Kinsler to regain some payroll flexibility.

Dombrowski’s astute roster manipulation led to four consecutive division titles and one pennant from 2011 to 2014. Several recent more suspect trades, free agent losses, and an apparently thin farm system give some pause as to how much longer the string can continue. But Dombrowski has demonstrated an uncanny knack for both rebuilding teams and keeping them competitive. With Dombrowski in charge Detroit should remain a relevant and competitive franchise.

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.