Well, lets take a look at the big stuff hes done.
Goodrow, I think he really identified what this team was missing and was willing to pay a premium for him. Thus far I am fine with it. He's having a career year and theres talk of a captaincy in his future. You are always going to have some "bad" contracts on every roster, if you are actively trying to build a winner. Overpayment, yes.
He did fine on the Lindgren extension. His numbers are pretty spectacular given his contract. I think every team would take the player and the deal. Very good deal, underpayment.
He struck out looking on the Nemeth deal. Bad player evaluation there, bad term but 2.5 really isn't an "overpayment" per se. Still, its not good.
Adam Fox, the very fact that he is signed to 7 years is amazing. Overpayment? Some would say it's under. Let's call it fair value.
Mika, pretty much the same thing. 8 years. 8.5 You can debate it. He runs hot and cold, but right now he is playing to market value. I'd say slight overpayment for the player - however, you are retaining a player you likely wouldn't be able to touch in the open market and one you would surely overpay if you could. Fair
Igor - extended for 4 years, 5.65. Best goalie in the world. One could argue, massive underpayment.
Reaves is looking like a fair deal for what he brings on and off the ice to the team. Fair
All in all its a decent job imo. I'm not a Drury lover or hater. Theres a lot left to be done. I think thus far the record speaks for itself and a more precise judgement of his cap control can be laid out after next summer.