Boston Red Sox biggest trades under Dave Dombrowski

Dave Dombrowski is known as one of the most aggressive executives in baseball. Let’s look at some of his biggest trades during his tenure with the Red Sox.

Dealin’ Dave was brought to Boston to win. At the time of his hiring in 2015, the Red Sox had a top-five farm system in baseball and were just finishing up their second consecutive season at the bottom of the AL East. He was just as advertised: fearless in his trades and careless in his management of the farm system. He departed in 2019 with a World Series ring on his finger and the worst farm system in the MLB.

Dave Dombrowski was the physical embodiment of the “swing big or miss big” philosophy. As a result, the rewards were sweet―three consecutive AL East titles and a 119-win championship season―but the consequences were painful, with the Red Sox coming off a disappointing third-place season and possibly facing another.

So without further ado, let’s look back at Dombrowski’s biggest trades from his tenure with the Red Sox.