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.