GMs are judged in hindsight. Right or wrong, that's just the way it is. I don't like assigning blame when things go wrong, and since we went from last to first, "going wrong" is debatable. I am often critical of individual moves by our GMs, but I don't think of it as "blaming them". They have enormous pressure on them to win now, and my philosophy is more about looking longer term. Theo even admitted he lost sight of the longer term in his later years in Boston.
I disliked DD's biggest moves at the time, so this is not Monday morning quarterbacking for me.
The biggest move was signing Price with an out option after 3 years. The money was absurd, but in today's market, he "got what he was worth". However, most big signings do not work out, even in the short term. I said at the time, I understood the great need to add an ace and that "Price was probably the best FA SP'er to come along in a long time." I don't "blame him" for signing him. I preferred Cueto, but I'm not trying to pretend I'm smarter than DD, Ben, Theo or Dan D. Now, in hindsight, the signing does not look good so far. He did not reach expectation in his first regular season, and that's when the big value was supposed to materialize. We all expected lower value in years 5-7, but not #1, although I did warn of the poor past history of these mega signings.
The next biggest deal was the Margot, Guerra, Allen and Asuaje. Sure, Guerra's stock has fallen, so the "hindsight" part of viewing the trade looks a little better than if he was doing well, but at the risk of beating a dead horse repeatedlymy argument at the time of the deal was that we gave up a lot of young talent for a relief pitcher. Then, when you figure he is being paid similar to free agent closer money, we double-dipped on the "overpay." Yes, I get the argument that Margot was blocked by Beni, but many here felt Beni was rushed, and the trade for Kimbrel was not the only trade option. The hindsight view of the trade has to look worse than it did at the time. Kimbrel did not pitch like a top 3 closer this year. That's what we thought we were getting. That's what I thought we were getting and I still hated the trade. I'm not going to say, "See, I told you so!" because I thought he would be a top 3 closer this year. My beef was not about him projecting decline, but the decline certainly makes the deal look worse to me now.
The third biggest deal was the Espi for Pomeranz trade. I hated the trade at the time, because I felt we should have looked to create a bigger package for a better starter. Pomeranz had pitched like an ace for just a half a season. We needed a starter. We were in a pennant race. I get why we did it. I'm not "blaming" DD for doing it, but I still think it was a gross overpay. I'm glad it was for 2 more years of team control with Pom, and I hope to hell he pitches well for us the next 2 years. I hate blaming a GM for an injury, but the fact is, so far, the Pom part of the trade has not lived up to expectations.
The Ziegler deal was probably his distant fourth biggest deal. I liked it at the time, even though the "other Basabe" looked promising. Ziegler did great for us. The deal was good in foresight and good in hindsight.
Overall, our roster looks strong. We have maybe 2-3 weak links, and the main core of our top prospects are still intact. This winter may be an even more defining time period for DD than last winter's glitzy bombshells.