His biggest blunder is not getting the big three together the summer of Nylander’s contract negotiation. This is how I would have played it out:
Shanny and Dubas walk into a room with the three players. Shanny puts his SC ring on the table. Dubas speaks we aren’t and can’t go above this dollar amount for your three if we want to have a team that competes night in and night out for a SC. We will give you players all 90% plus in signing bonus which makes these contracts buyout and lockout proof but by doing so you have to come down in cost or give us extra term. Here is a Certified Financial Planner to explain the Present value of money Vs Future value. This is what we have worked out as each of your comparable player contracts. So you three look to your teammate to your left and look your teammate to your right and ask yourself is playing together, making millions and having a team that has this level of talent competing for a SC year in and year out what’s important to you or is making a few extra hundred grand at the expense of being one of the best teams in the NHL? Hopefully we can come to an understanding because we want all three of you to be TML lifers. Make it happen.
That being said overpayment on your stars to the tune of 2-3 million is not the worst thing in the world. His biggest issues have been dealing with some of the awful contracts he was saddled with from Lou. Zaitsev was IMO masterfully done. Do I like Ceci, no but to get away from Zaitsev and not have to retain was a deal and a half. Marleau cost them a 1st. Everybody knew the third year was going to kill the TML, we did what we had to do to keep the big three together.
He has signed some very good contracts in Kap, AJ, Kerfoot and now Holl. He also brought Mikheyev and fired Babcock. The Babcock firing should have been done last spring IMO but a rookie GM firing the highest paid coach in the NHL is no small feat. Hopefully he has learned a thing or two regarding negotiations to carry forward to signing the next round of players.