With Dave Dombrowski facing his first trade deadline as the Phillies’ president of baseball operations, here’s a look at his most prominent deals during his tenures with the Montreal Expos, Florida Marlins, Detroit Tigers, and Boston Red Sox.

Montreal Expos

July 13, 1988

Traded catcher Jeff Reed, outfielder Herm Winningham, and pitcher Randy St. Claire to Cincinnati for outfielder Tracy Jones and pitcher Pat Pacillo.

Comment: Dombrowski made his first deal just eight days after replacing Bill Stoneman as Montreal’s general manager. It wasn’t a particularly significant one.

Aug. 8, 1989

Traded pitcher Zane Smith to Pittsburgh for third baseman Willie Greene, pitcher Scott Ruskin, and outfielder Moises Alou.

Comment: Smith went 6-2 with a 1.30 ERA in 11 games to help the Pirates win their first National League East title since 1979 that season, and then helped them win two more division titles as a mainstay in their rotation in 1991 and 1992. Dombrowski still got the better of the deal because Alou emerged as a star for six seasons with Montreal. Dombrowski later traded Ruskin and Greene along with Dave Martinez to get closer John Wetteland from Cincinnati.

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Florida Marlins

June 24, 1993

Traded pitchers Trevor Hoffman, Jose Martinez, and Andres Berumen to San Diego for infielder Gary Sheffield and pitcher Rich Rodriguez.

Comment: It was the second time in his career that Dombrowski dealt away a young pitcher (Hoffman) who would become a Hall of Famer. He also traded Randy Johnson from Montreal to Seattle in a non-deadline deal in May 1989. But this deal still turned out pretty well for the Marlins. In parts of five seasons with the Marlins, Sheffield hit .288 with 122 home runs and a .970 OPS. He also hit .320 with three homers during Florida’s run to a World Series title in 1997.

July 17, 1993

Traded pitcher Cris Carpenter (not Chris Carpenter) to Texas for pitchers Kurt Miller and Robb Nen.

Comment: This seller deal for an unknown 23-year-old reliever proved to be a huge win for the Marlins. Nen saved 118 games over five seasons and was the closer for Florida’s 1997 World Series title team.

July 21, 1997

Traded outfielder Billy McMillon to the Phillies for first baseman/outfielder Darren Daulton.

Comment: Dombrowski said, “It’s one of the best moves for me personally and for the Florida organization because it helped us win a world championship.” Daulton hit .389 in the Marlins’ seven-game World Series win over Cleveland that year.

May 14, 1998

Traded pitcher Manuel Barrios, catcher Charles Johnson and outfielders Gary Sheffield, Bobby Bonilla, and Jim Eisenreich to the Los Angeles Dodgers for catcher Mike Piazza and third baseman Todd Zeile.

Comment: This was a massive salary dump ordered by ownership just six weeks after the Marlins handed out their World Series rings. The challenge would be to see what Dombrowski could get for Piazza, the best catcher in the game at the time.

May 22, 1998

The Piazza answer came eight days later when the future Hall of Famer was dealt to the New York Mets for outfielder Preston Wilson and pitchers Geoff Goetz and Ed Yarnall.

Comment: Piazza obviously became the best player in the deal, but Wilson hit .262 with 108 doubles and 104 home runs during five seasons with the Marlins. Better still, in an offseason trade with the Yankees, Dombrowski used Yarnell to acquire a prospect named Mike Lowell, the eventual offensive centerpiece of the Marlins’ 2003 World Series title team.

July 8, 1999

Traded pitcher Matt Mantei to Arizona for pitchers Vladimir Nunez and Brad Penny, plus outfielder Abraham Nunez.

Comment: This was another seller deal that helped set the foundation for a second World Series title for the Marlins. Dombrowski was in Detroit when Florida won in 2003, but Penny was still around and won two games against the Yankees in the World Series.

July 25, 1999

Traded pitcher Livan Hernandez to the San Francisco Giants for pitching prospects Nate Bump and Jason Grilli.

Comment: Neither Bump nor Grilli ever helped the Marlins.

» READ MORE: Phillies should buy big if they’re going to buy at the MLB trade deadline (but they should sell) | Marcus Hayes

Detroit Tigers

July 5, 2002

In his first deadline deal with the Tigers, Dombrowski was a seller, trading pitcher Jeff Weaver to the Yankees as part of a three-team deal that also included the Oakland A’s. The Tigers got first baseman Carlos Pena and pitchers Jeremy Bonderman and Franklyn German from Oakland.

Comment: Weaver left the Yankees after two below-average seasons, while Bonderman became a back-of-the-rotation starter for eight years in Detroit and had an outstanding postseason in 2006 when the Tigers reached their first World Series in 22 years.

July 31, 2006

Traded pitching prospect Brian Rogers to Pittsburgh for veteran first baseman Sean Casey.

Comment: The Tigers had a huge lead in the American League Central, and this was Dombrowski’s first chance to be a buyer since moving to Detroit. Casey wasn’t particularly good during the final 53 games of the regular season, but he was incredible during the first postseason of his career, hitting .432 (16-for-37) with five doubles, two home runs and nine RBIs. He also played very well for Detroit the following season.

July 30, 2008

Traded catcher Ivan Rodriguez to the Yankees for pitcher Kyle Farnsworth.

Comment: The Tigers were two games over .500 and five games out of first place when Dombrowski made this deal involving two big-name players. The trade did not help either team.

July 31, 2009

Traded pitching prospects Luke French and Mauricio Robles to Seattle for pitcher Jarrod Washburn.

Comment: The Tigers were in first place by one game at the deadline, and Dombrowski thought the acquisition of Washburn, who had a league-best 2.64 ERA in 20 starts with the Mariners that season, would push his team over the top. Instead, Washburn went 1-3 with 7.33 ERA in eight starts with Detroit, and the Tigers lost a 163rd game to Minnesota for the AL Central title. Washburn never pitched again. The good news for Dombrowski is that he didn’t give away anything in French and Robles.

Aug. 17, 2009

Traded minor-league pitcher Brett Jacobson to Baltimore for veteran first baseman/designated hitter Aubrey Huff.

Comment: This deal after the waiver deadline was also flop. Huff hit .189 with two home runs and a .567 OPS in 40 games for the Tigers. The following season, after signing as a free agent with San Francisco, he finished seventh in the NL MVP voting and helped the Giants win the World Series.

July 28, 2010

Traded minor-league pitcher Giovanni Soto to Cleveland for shortstop Jhonny Peralta.

Comment: The move did not help the Tigers much in 2010, but Peralta emerged as an offensive force in Motown and helped the team win three straight division titles and an American League pennant. It goes down as one of Dombrowski’s best-ever deadline deals.

July 30, 2011

Traded outfielders Francisco Martinez and Casper Wells and relief pitchers Charlie Furbush and Chane Ruffin to Seattle for starting pitcher Doug Fister and reliever David Pauley.

Comment: Fister went 8-1 with a 1.79 ERA to help the Tigers win the division in 2011 and remained a sensational No. 3 starter behind Justin Verlander and Max Scherzer in 2012 and 2013 as the Tigers won two more division titles. It was another deadline gem for Dombrowski.

Aug. 15, 2011

Traded pitchers Cole Nelson and Lester Oliveros to Minnesota for outfielder/DH Delmon Young.

Comment: Young was pretty good in his two regular seasons with the Tigers and great in the 2011 and 2012 postseasons, hitting .280 with eight home runs and15 RBIs in 22 games. He won the ALCS MVP in 2012.

July 23, 2012

Traded catcher Rob Brantly and pitchers Brian Flynn and Jacob Turner to Miami for infielder Omar Infante and pitcher Anibal Sanchez.

Comment: Another lopsided winner for Dombrowski. Sanchez was good in 12 regular-season starts in 2012, then great in the postseason (1.77 ERA in three starts) to help the Tigers reach the World Series. The following year, he was 14-8 with a league-best 2.57 ERA. Infante, in his second stint with the Tigers, was a terrific bench player.

July 29, 2013

Traded outfielder Danry Vazquez and pitcher David Paulino to Houston for reliever Jose Veras.

Comment: Veras provided the Tigers with bullpen help in 2013, then signed with the Cubs after the season. It was a rental that did not cost the Tigers anything.

July 30, 2013

In a three-team deal with Boston and the Chicago White Sox, Dombrowski traded outfielder Asivail Garcia to the White Sox, and pitcher Brayan Villarreal to the Red Sox. Detroit got infielder Jose Iglesias from the Red Sox.

Comment: Garcia became an All-Star for the White Sox, and Iglesias gave the Tigers a slick-fielding shortstop.

July 23, 2014

Traded pitchers Corey Knebel and Jake Thompson to Texas for closer Joakim Soria.

Comment: In an attempt to improve one of the worst bullpens in baseball, Dombrowski acquired Soria to join Joe Nathan as the team’s late-inning relievers. Soria had two awful appearances in the Tigers’ three-game ALDS series loss to Baltimore, and Detroit has not been back to the postseason since.

July 30, 2014

In a three-team deal with Seattle and Tampa Bay, Dombrowski traded outfielder Austin Jackson to the Mariners, and pitcher Drew Smyly and infielder Willy Adames to the Rays. The Tigers got pitcher David Price from Tampa Bay.

Comment: Price was 13-8 with a 2.90 ERA in 32 career starts with the Tigers and was terrific in a Game 3 start against the Orioles in the playoffs. But it was in a series-ending losing effort. Jackson’s career went south in Seattle, but Adames and Smyly were productive for the Rays.

July 30, 2015

Traded David Price to Toronto for pitcher Matt Boyd, Jairo Labourt, and Daniel Norris.

Comment: Dombrowski was a seller in his last trade deadline with Detroit, and he got an OK return for Price, who was brilliant for the Blue Jays in the regular season and awful in the postseason. Boyd and Norris have had up-and-down careers with the Tigers.

Traded Joakim Soria to Pittsburgh for outfielder JaCoby Jones.

Comment: Jones is still with the Tigers but not because he has played well.

July 31, 2015

Traded outfielder Yoenis Cespedes to the New York Mets for pitchers Luis Cessa and Michael Fullmer.

Comment: This was Dombrowski’s final move with the Tigers. He was fired four days later. Cespedes helped the Mets reach the World Series. Fullmer had two good seasons with the Tigers, then two awful ones, and is now pitching in relief.

Boston Red Sox

July 7, 2016

Traded infielder Wendell Rijo and pitcher Aaron Wickerson to Milwaukee for third baseman Aaron Hill.

Comment: Third base was the weakest link for Boston’s powerful offense, but the veteran Hill did not provide an improvement over Travis Shaw. A nominal fee was all it cost to find out.

July 9, 2016

Traded pitcher Josh Almonte and infielder Luis Alejandro Basabe to Arizona for reliever Brad Ziegler.

Comment: Ziegler was a terrific two-month rental, posting a 1.52 ERA and picking up four saves in 33 games.

July 14, 2016

Traded pitching prospect Anderson Espinosa to San Diego for pitcher Drew Pomeranz.

Comment: Pomeranz struggled to the finish with the Red Sox before bouncing back with a terrific year in 2017 to help Boston win a second straight division title. He struggled again in 2018. Espinosa was considered one of the best pitching prospects in baseball at the time, but an injury derailed his career.

July 26, 2017

Traded Shaun Anderson and pitcher Gregory Santos to San Francisco for infielder Eduardo Nunez.

Comment: This deal was another theft for Dombrowski. Nunez became a tremendous super utility player for the Red Sox and hit a three-run, pinch-hit home run in Game 1 of the 2018 World Series.

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July 31, 2017

Traded pitchers Gerson Bautista, Jamie Callahan and Stephen Nogosek for reliever Addison Reed.

Comment: Reed was a two-month rental who helped in the regular season, then signed with the Twins after the season.

June 28, 2018

Traded infielder Santiago Espinal to Toronto for utilityman Steve Pearce.

Comment: Pearce was really good in the final two months of the regular season and a superstar in the postseason, winning World Series MVP honors by hitting .333 with three home runs and eight RBIs.

July 25, 2018

Traded reliever Jalen Beeks to Tampa Bay for pitcher Nathan Eovaldi.

Comment: Eovaldi was Boston’s most valuable pitcher during its 2018 World Series run. In six appearances, including three in relief during the World Series, he was 2-1 with 1.61 ERA.

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July 30, 2018

Traded pitchers Ty Buttrey and Williams Jerez to the Los Angeles Angels for infielder Ian Kinsler.

Comment: Kinsler, at a low cost, gave the Red Sox one more veteran presence for their World Series run.

July 13, 2019

Traded outfielder Elio Prado and infielder Noelberth Romero to Baltimore for pitcher Andrew Cashner.

Comment: Cashner, it turned out, was at the end of his career and no help to the Red Sox. Dombrowski, surprisingly, would soon be fired, too, just 11 months after winning the World Series.