Top 10 most significant winter meeting moves of Dave Dombrowski’s career

For four days in December each year, the baseball world convenes to discuss league matters and, naturally, conduct some deals.

After more than three decades leading baseball front offices, Phillies president of baseball operations Dave Dombrowski is a winter meetings veteran. Ahead of the 2024 iteration set to begin on Monday in Dallas, here’s a look at the 10 most consequential moves he’s made.

Taijuan Walker’s four-year, $72 million contract is the most controversial deal on the Phillies’ books. But since it was a major deal signed during a busy 2022 winter meetings for Dombrowski, it lands on this list.

When Walker was moved back to the bullpen after prolonged struggles during the 2024 season, he became one of the most expensive mop-up guys in baseball. He will enter spring training without a guaranteed spot on the team, with the Phillies still on the hook for $36 million.

At the end of the 2014 winter meetings in San Diego, then-Tigers GM Dombrowski acquired outfielder Yoenis Céspedes and pitchers Alex Wilson and Gabe Speier from the Red Sox in exchange for pitcher Rick Porcello.

Across 51 games with the Red Sox, Céspedes batted .269 with five home runs and 33 RBIs. Céspedes was shipped to the Mets at the 2015 trade deadline for pitching prospect Michael Fulmer, who won the 2016 AL Rookie of the Year.

Dombrowski also reaped the benefits of the other side of the trade once he moved to Boston’s front office in August of 2015. Porcello won the 2016 AL Cy Young and was part of the World Series-winning team in 2018.

» READ MORE: Let’s make a deal: Trade ideas for the ‘open-minded’ Phillies with Alec Bohm, Ranger Suárez, and more

During the 2016 winter meetings in Maryland, Dombrowski — then with the Red Sox — secured a defensive upgrade at first base with free agent Mitch Moreland.

Moreland signed a one-year, $5.5 million contract, and signed a two-year extension the following season.

An All-Star in 2018, Moreland also had a big moment during the 2018 World Series. With the Red Sox down 4-0 to the Dodgers late in Game 4, a pinch-hitting Moreland sparked the comeback with a three-run home run. Boston went on to win Games 4 and 5 to clinch the Fall Classic.

When Dombrowski signed lefty Matt Strahm to a two-year, $15 million contract during the 2022 meetings in San Diego, some considered it an overpay.

But Strahm became a key piece in the Phillies’ bullpen, and earned an extension in March. At the 2024 All-Star Game, Strahm joined Jeff Hoffman as the Phillies’ first pair of All-Star relievers.

During the 2005 meetings in Orlando, Dombrowski signed left-handed starter Kenny Rogers to a two-year, $16 million deal, and also brought back right-handed reliever Todd Jones on a two-year, $11 million deal.

Both veterans helped the Tigers to their first postseason appearance since 1987. Rogers put up a 17-8 record and a 3.84 ERA in the 2006 regular season. At age 41, he became the oldest pitcher to win a World Series game with his eight shutout innings in Game 2 — though that game marked Detroit’s only win in the 2006 Fall Classic against the Cardinals.

Jones, who played for the Tigers from 1997 to 2001, became Detroit’s all-time saves leader in 2006 with 235. He also made seven postseason appearances that year, and took over for Rogers to close the ninth inning of Game 2 of the World Series.

Following Florida’s 1997 World Series victory, Marlins owner Wayne Huizenga directed Dombrowski to cut payroll. And so began the 1997 Marlins fire sale, which saw many of their best players shipped off. That included Kevin Brown, who a few months prior had pitched a complete game — while suffering from the flu — to clinch the National League Championship Series over the Braves.

Dombrowski sent Brown to the Padres in exchange for three young players: first baseman Derrek Lee and pitching prospects Steve Hoff and Rafael Medina. Brown only spent one season in San Diego, but it was an impactful one. After posting an 18-7 record with a 2.38 ERA, Brown finished third in NL Cy Young voting. He also helped lead the Padres to the 1998 World Series, though they lost in four games to the Yankees.

Lee, on the other hand, turned out to be a core player on the Marlins’ 2003 World Series-winning team.

From 1992 to 1998, major league general managers did not attend the winter meetings. Although this deal may not have been officially made on site in New Orleans, it took place on the final day of the scheduled meetings and is widely considered a winter meetings move.

» READ MORE: The Phillies don’t want to move Bryce Harper back to the outfield. Given the free-agent alternatives to Juan Soto, maybe they should.

During the 2016 meetings in Maryland, Dombrowski bolstered Boston’s starting rotation with a trade for White Sox lefty Chris Sale. In exchange, the Red Sox sent top prospect Yoán Moncada to Chicago, as well as outfielder Luis Alexander Basabe and right-handers Michael Kopech and Victor Diaz.

Sale was an AL Cy Young runner-up in 2017 after posting an MLB-leading 308 strikeouts, and then was a crucial part of the Red Sox’s 2018 World Series victory. The lefty closed the final inning of Game 5, striking out Manny Machado to clinch the title.

To fill a gap at shortstop during the 2022 meetings, Dombrowski signed Trea Turner to the second-largest contract in Phillies history in terms of total value. The $300 million, 11-year deal will keep Turner in Philadelphia through 2033.

Over the past two seasons since putting pen to paper, Turner has hit .280 with 47 home runs and 49 stolen bases. He’s also inspired a Netflix documentary.

At the 2009 meetings in Indianapolis as GM of the Tigers, Dombrowski helped orchestrate a three-team trade with the Yankees and Diamondbacks that brought Max Scherzer to Detroit.

As part of the deal, the Tigers also received left-handed pitchers Daniel Schlereth (Diamondbacks) and Phil Coke (Yankees), and outfielder Austin Jackson (Yankees). The Diamondbacks received right-handers Edwin Jackson (Tigers) and Ian Kennedy (Yankees), while the Yankees received outfielder Curtis Granderson (Tigers).

Jackson became a solid center fielder for Detroit, and Scherzer became their ace. He helped the Tigers to the World Series in 2012, when they lost to the Giants, and won his first Cy Young Award in 2013.

» READ MORE: Phillies prospect Justin Crawford living ‘a dream’ playing for Team USA and thriving on an international stage

In one of the biggest blockbusters in the history of the winter meetings, Dombrowski brought Miguel Cabrera to Detroit in 2007 in a six-for-two player swap with Miami. In exchange for Cabrera and right-handed pitcher Dontrelle Willis, the Tigers sent outfielder Cameron Maybin, pitcher Andrew Miller, catcher Mike Rabelo and minor league pitchers Eulogio De La Cruz, Dallas Trahern and Burke Badenhop to the Marlins.

Maybin and Miller were two of the Tigers’ top prospects, but in exchange, Dombrowski received a franchise player and one of the greatest hitters of all time. Cabrera retired in 2023, and joined Hank Aaron and Willie Mays as the only three players in MLB history with a career batting average above .300, 3,000 hits, and 500 home runs.