If he keeps having successful trades, doesn't that prove that DD knows exactly what he's giving up? Yes, the Tigers swam in mediocrity his last few years, but I doubt there is even one trade that he or Tiger fans regret now. It's pretty remarkable to look at his trade history in Detroit.Except... I do kind of think this. To be clear, I don't think he's stupid. I think he identifies players he wants and doesn't really care that much about the value proposition involved in getting them. Because of this he does consistently overpay -- regardless of whether the moves work out or not, he consistently gives up more than the market expects. That's not an accident or a brainfart, it's a strategy. And it's why people always describe him as "decisive" and "aggressive."
I think there are two separate valid concerns about this strategy, by the way, and I apologize if I've brought this up elsewhere. One is that it's just basically the wrong strategy -- that the playoffs are a crapshoot, so once you're a team that's likely to make the playoffs (let's say, an 88-win team), overpaying in future assets to continue to marginally improve your chances is a sucker bet. The other, though, is maybe more interesting: If you care less about the value proposition than you do about getting Your Guy, then it adds a ton of pressure on you to be right about picking Your Guy. And Dombrowski's record on that so far is decidedly mixed (although Kimbrel's resurgence this year helps his case a lot).
This game is a crapshoot, but hoarding mediocre prospects will not change this teams future.