When you really pick apart DD's tenure it is nothing special, but also similar to Gillick in that he was the right change at the right time. He inherited Nola, Wheeler, Hoskins, Harper, JT, Bohm, Stott and even Rojas. Didn't really take a genius to extend the guys he did, or buy Trea Turner. I'll give him a wash on Schwarber/Casty. He did not really give this team a Werth, but this year's angst aside, his bullpen building has been solid. He's playing the cards he had, and hasn't mortgaged the future the way the Gillick and Amaro did even if he's still not getting it right. And Barber wasn't his hire either, but he kept him, and it's certainly the DD/Fuld/Mattingly development regime by now.
But as far as this thread goes, I don't think he has lost a trade. Not even O'Hoppe/Marsh. And he wasn't fleeced in terms of giving up Ben Brown or the two guys for Estevez. Both teams agreed on everyone's value, there wasn't a smarter team who saw something in our guys that we didn't.
Gonna be an interesting deadline either way.