Between 06-07 to 10-11, there were many mistakes due to risky choices. DL was beginning to build a defense around Johnson and Hickey, and were a couple points from going with Bogosian I guess. That's your potential defense from a build from the net out GM.
The Richards risk was not working. They were this close to missing the playoffs, until they lucked into Carter crying about being in Columbus. Had he been happy there, what does(or could) DL do to save his job in 2012?
The complicated mixture all ended up working, but the steps that got them there aren't what I'd call unswerving. DL's whole plan was on the knife's edge often. Thankfully Williams didn't get injured again. Well, he did, but just that first full year here. Thankfully Mitchell didn't sustain more concussions. He did get hurt many times, including whatever it was in 2013, but the gamble paid off.
Like the veterans on the roster, DL had his time. A lot had to go right, because a lot went wrong, even before mid June 2014. Talk about the knife's edge. By all rational thought, they should've lost to SJ in 2014. Had that season ended with a thud, maybe they would've had the 2015 and 2016 picks, certainly get rid of Richards, let Gaborik and Greene walk, maybe even end up trading Kopitar, since they would've been just a 1 hit wonder that got extremely hot at the right time for a couple months.
You enjoy the Cup years, because it's exceedingly difficult to win. However, without lucking out on Carter, the culmination of DL's plan was a team that was fighting for 8th in the conference. That's with landing Doughty, who you could actually build a defense around. Maybe win a bad division that year, since the Coyotes were 6th in the conference.