Trading for Max Scherzer was a huge win for Dombrowski
Back to Dombrowski's time with the Tigers, the Tigers were right in the middle of their big push to contend and they needed some pitching. So, Dombrowski was able to swing a three team deal with the Yankees and Diamondbacks that sent Curtis Granderson and Edwin Jackson to the Diamondbacks, but netted Max Scherzer and Austin Jackson in return.
Again, the Tigers gave up some good players here. Jackson hung around the league seemingly forever as a serviceable starting pitcher for basically every team in the league at some point. Curtis Granderson put together a couple really good seasons with the Yankees and was a very solid player for a long time.
Austin Jackson was decent enough and saved the Tigers some cash since Granderson was getting pricey when Detroit moved him. As for Scherzer, he was pretty good his first couple of seasons in Detroit, but he took off in 2012 and in 2013, he won his first Cy Young Award. All told, Scherzer made 161 starts for the Tigers with a 3.52 ERA and 1081 strikeouts in 1013 innings. He has since gone on to be one of the best pitchers of this generation and is a mortal lock for the Hall of Fame once he decides to call it quits.
We have no idea what Dombrowski was thinking when he traded Eugenio Suarez for Alfredo Simon
Some trades are just bad with the benefit of hindsight, but others were bad ideas at the time and then aged like milk. The Tigers were in need of starting pitching before the 2015 season and the Tigers had a glut of young infield prospects at the time. So, to shore things up, he decided on making a trade with the Reds for Alfredo Simon that cost them Jonathan Crawford and Eugenio Suarez.
Losing Suarez was rough even with all of the young talent the Tigers had at the time. Suarez was one of the better hitters in the league from 2017-2019 with the Reds. However, this deal was still a bad idea at the time because Simon was an off the field disaster. He had involuntary manslaughter charges against him from 2011 and before the trade in 2014, he was sued for allegedly raping a woman in Washington DC. Simon ended up posting a 5.05 ERA with the Tigers that season and was in indy ball a year after that.