Phillies: 3 trades where Dave Dombrowski screwed up, 3 where he was a genius

The Philadelphia Phillies' president of baseball operations Dave Dombrowski has a long history of making very aggressive trades regardless of the time of year and being willing to commit big-time dollars to keep stars in the fold. While this has often meant that Dombrowski has often left organizations with bare farm systems and challenging contracts on their books, it is hard to deny the results he has gotten in his career with several different organizations.

While Dombrowski got his first general manager job with the Montreal Expos way back in 1988, it was his time as the Marlins' general manager where he began to garner a reputation as a guy that targeted big names to try and win championships quickly. The strategy has been successful as he has two World Series rings from 1997 and 2018 along with several other deep playoff runs.

With as many big swings as Dombrowski has taken (and will take), there are going to be some absolute banger trades as well as some that will make fanbases wince just at the mention of them. With the trade deadline coming up, lets take a look at the best and worst Dave Dombrowski trades.

Here are the best and worst trades of Dave Dombrowski's career

You won't see any Phillies trades on this list because 1) the bar for making this list is very high in either direction and 2) Dombrowski hasn't really been in Philly long enough to judge his trades too much. Some of these trades look great/terrible just with the benefit of hindsight while others were just objectively awesome/horrifying even at the time. We are just judging based on the results here, but will mention the thought process where it makes sense.

Anyways, lets get on to the best and worst trades of Dave Dombrowski's career.

The trade for Miguel Cabrera is a career highlight for Dave Dombrowski

When the Detroit Tigers hired Dave Dombrowski, they were looking to swing for the fences in order to finally bring a World Series title back to Detroit. After a few years of rebuilding what was a truly terrible roster when he got there, Dombrowski swung a huge trade with the Marlins where he acquired future Hall of Famer Miguel Cabrera along with Dontrelle Willis for Cameron Maybin, Andrew Miller, Eulogio De La Cruz, Mike Rabelo, Burke Badenhop, and Dallas Trahern.

In fairness to the Marlins, there were some good players in this deal. Cameron Maybin was a very highly regarded young player at the time and ended up putting together a 15 year career in the majors. Andrew Miller took a while to get going, but ended up making two All-Star teams as a reliever. Neither did much with the Marlins, sadly.

Willis was decidedly not good in Detroit and never did regain the form he had early in his career with the Marlins, but the star of this trade was clearly Miggy. Sure, he is a shadow of his former self these days and the Tigers certainly shouldn't have given him the contract he is currently on, but Cabrera also won two MVP awards, a Triple Crown, and a slew of All-Star Game appearances in a Tigers uniform. That is a win.

Dave Dombrowski probably wishes he could take the Randy Johnson trade back

While Dombrowski is best known for his time with the Tigers, Red Sox, and Phillies, most people may not be aware that he got his start as a GM with the Montreal Expos in the late 80's. Dombrowski was the youngest GM in the league and during this time, he still was looking to make splashes and Mark Langston was one of the better pitchers available on the trade market at the time. So in 1989, the Expos swung a trade for Langston and Mike Campbell by sending Brian Holman, Gene Harris, and a young pitcher by the name of Randy Johnson to the Mariners.

Yeah, that Randy Johnson. Johnson famously took several years to be able to throw strikes consistently including his time with the Mariners. However, once he DID figure things out, he became one of the best pitchers of his generation (and certainly the most feared) that culminated in his induction into Cooperstown. We can't necessarily blame Dombrowski for making the move, but woof does this one look rough with the benefit of hindsight.

Chris Sale's contract is terrible, but Dombrowski's trade for him turned out great

Okay, okay...we know. Chris Sale's contract with the Red Sox looks really bad right now given all of the injuries that Sale has been dealing with. That is absolutely true. However, the trade is a different story entirely. Back before the 2017 season, Dombrowski was about to enter his first full season as the head honcho of the Red Sox and he made yet another blockbuster move as he acquired Chris Sale from the White Sox for Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz.

There was certainly a chance this trade could have gone south as Moncada and Kopech were huge talents at the time and Sale was, well, a pitcher. However, while the White Sox certainly got some value back in the trade, Boston got exactly what they wanted out of Sale early on. He was one of the best pitchers in the American League in 2017 and 2018 with a combined 2.56 ERA and 545 strikeouts in 372.1 innings.

You take that every time from a trade even if the subsequent contract he signed in 2020 has been less than inspiring.

Dombrowski traded Doug Fister to the Nationals for basically nothing

Younger baseball fans may not remember Doug Fister. He was perennially underrated even back then as a guy who consistently put up low to mid 3 ERAs each season. However, the Tigers were facing a bit of a payroll crunch and Fister was about to make a lot of money in arbitration, so they decided to move Fister. The Tigers settled on trading him to the Nationals for pitching prospects Robbie Ray and Ian Krol.

Teams can't keep every guy, but you want to get value in your trades and this one was a stinker on that front. Robbie Ray ended up figuring things out eventually and won a Cy Young in 2021. However, that was long after he left the Tigers' organization as Ray only played part of one bad season with Detroit. Krol was meh to bad for two seasons in the Tigers' bullpen before moving on to be meh to bad elsewhere over the next few seasons. Certainly not the return you want for a guy that would go on to finish in the top 8 of Cy Young voting in his first season with the Nationals.

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