I'm not sure how that Escobar trade is anything but an A at this point. It was an expiring contract in a year the team was going nowhere.
My issue with all of the "buy" trades was they aimed low. Like they were hedging their bet, instead of really going for it.
I recall the angst many here had about trading Ynoa, and how those people were pretty much ridiculed for thinking the Twins couldn't afford to deal a low A prospect for a legit MLB pitcher.
The Pressley trade is the only one that I think (of the sales) you can really question. That said, the two guys they got should be better at some point.
Getting anything for Diaz was good. Signing him in the first place was VERY questionable. They had the most or near most international room that year, and signed a 1B. Mind. Boggling.
So? Inspiring? Not really, yet. Terrible? The only two you can question, and one of those is pure hindsight, is Ynoa and Pressley. Mostly they deal guys with not much value for guys that have not yet (and maybe never will) provided much value.
Really, the issue is NOT being more bold. Trading off good/great players for better prospects, or trading better prospects for better MLB players. Much like the last FO, pretty much very conservative.