There's nothing wrong with liking his trades, especially after 2018.
I liked several of them myself, including the Thornburg trade, as i didn't see any reason why it would be the absolute disaster that it was. Had Thornburg actually pitched like he did in Milwaukee, would anyone really be complaining about Dubon? Getting a pre-arbitration closer should cost a bit. Look at other teams prices for them. (Ken Giles to Houston, for example.)
But I am wondering if Henry really signed off on any of this beforehand. Did he just let DD do things, as long as they worked out? After 3 straight division titles and a WSC, one has to think DD should have some autonomy.
Carson Smith? Reportedly Seattle was happy to deal him due to their fear of arm troubles. DD really didn't give up much, but he also got nothing.
Kimbrel was an overpay IMO based on that we gave up two top 100 prospects at the time, plus a third who eventually became one, and also took on the entire contract. Usually if you pay full fair, the trade price goes down.
For Sale, Moncada was a lot and so was Kopech. But Sale was on one of the best contracts in MLB. He was supposed to cost a lot. Sort of the opposite of the Kimbrel deal where Kimbrel's contract was, at the very least, fair to high for his position.
Espinoza for Pomeranz seemed stupid at the time, but given how Espinoza fell apart, one has to wonder maybe DD had some inkling of his condition? I mean, maybe he at the very least figured "High ceiling, but the arm is risky." I can see that. And Pomeranz pitched very well for the Sox for a while, and even made an All Star team. Not a bad trade, IMO.
It did seem like the funds suddenly dried up this offseason. Like Henry finally said "Whoa. you're spending how much? We have limits here. high limits, but still limits." And DD thought "Wait. I need a closer. Oh well. At least I got Colten Brewer finally ." Otherwise, why bring back Pearce and Eovaldi for the whole off-season budget while letting Kimbrel and Kelly walk without replacement, unless there was a change in the plans midstream?
That's why I don't think Henry was even involved until he started getting the bill. Really the only other option is that DD is an idiot...