In terms of all the low risk deals vs all high risk deals, I think DD has done better with the low risk ones.
Of course, I loved the Chris Sale deal better than any other deal. Yes, the JD trade worked like magic right off the bat. The Price deal looks better now than it did just before the 2018 playoffs. The Kimbrel & Pom deals are also in this group. IMO.
I'm guessing we put the Moreland, Pearce and Nunez signings into the low risk category, and maybe the Travis Shaw/ Dubon for Thornburg in there, too. I'm sure there are other not-so-good low risk deals and some so-so like A Reed, Abad, Fister, Kinsler, and others.
I didn't mean to imply DD has done poorly with his big signings; he's actually done very well, but I think he seems masterful at the mid range, under-the-radar deals, especially the mid season ones..