I feel Chevy gets an unfair judgement in this arena. He was given some sever Cap restrictions and therefore, not able to do much. Holland on the other hand, made some of the worst contracts I have ever seen while in Detroit. He ensured an aged, slow, and probably the worst NHL team I have ever watched with the Red wings. I am a fan of his signings this off-season in Edmonton, but I much prefer the ability of Chevy to develop talent within, and keep trade talks virtually unheard. I give Chevy the edge, as he has made many great moves and built a team that makes the playoffs on a regular basis. Holland drove a club into the laughing stock of the NHL, and is now handed a team with 2 of the best players in the world. Pressure is on him at this point.
I rank Cheveldayoff as the NHL’s best GM. He seems to win most of his trades usually by being patient.