Mike Ilitch has done it all for Detroit.
Since buying the "Dead Wings" (as they were called) in 1982 for $8 million dollars, Ilitch has seen the Red Wings win four Stanley Cups since 1997 and has helped bring hockey back to "Hockey Town".
Ilitch isn't just interested in the Red Wings either, as he owns the Detroit Tigers and also owns the Michigan-based Little Caesar's franchise.
The Red Wings have made the playoffs for 20 straight seasons, and Ilitch's ability and willingness let his GM (currently Ken Holland) spend the money necessary to sign free agents and re-sign current players has given his team a distinctive advantage over other teams.
Ilitch also values veteran players in a way that no other NHL owner seems to do.
Additionally, Ilitch is very involved with his team and often plays a big part in keeping a player in Detroit for the duration of their career if they have spent the bulk of it in Detroit already.
Ilitch's recent success (last 15 years) with winning the Stanley Cup, and last 20 seasons making the playoffs gives him the number one spot on my greatest GM list.
Thoughts and comments are welcome, I will take up any disputes and discussions regarding this list.