I don't think the Kane deal was a bad deal in that they didn't give up much, and he wanted to be here, I think you had to take the chance to add him given those circumstances. The result was a failure, no argument there. I also don't think the decision was get Kane or go get someone else instead. I think it was adding Kane by making many cap money saving moves or do nothing else. I never got any impression Drury was going to do something else if Kane wasn't here. You could get on him for that decision, meaning he should have been looking to add someone else instead of Kane, but I do think that was his decision based on all the info at the time, Kane or done.
His trade DL two years ago was hugely successful, the best thing on Drury's resume as Pres/GM IMO, and it helped us make a fun run to the ECF. Last year not so much as he didn't add the right type of player(s) we needed. I did like the Tarasenko and Mikkola trade though, I just don't think he added the right players around that trade to add what the team lacked.
I'll also add, if you judge the trade DL simply on did the team win the Cup, then 99.9% of all teams fail every single season at the trade DL, I don't think that is how you judge it. If you have a good run, win some series, and get a lot of exciting moments, that matters. No parades, but if it is title or failure as your only two choices, that is a tough way to live, while clearly acknowledging the ultimate goal was not reached if you don't win the title.