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.