DD did a great job. He was hired to open the wallet and get a ring and he succeeded. Not just that he did make some great trades along the way. Steve Pearce, without him who knows what happens in that Dodgers series. Nate was also a huge part of the 2018 ring that he traded for. Craig Kimbrel was a great trade and obviously Chris Sale.
The only move that I didn't like at the time was the last deal with Sale. It still mind boggling to this day why he would extend him for 5 years with a bad arm/shoulder.
Prospects are great but they don't all pan out.