I don't think Jimmy D gets enough love. He's a legendary hockey figure, has impacted the sport on a profound level, and is truly the man behind the curtain and the backbone of this franchise.
Imagine all the dumb crap Holland would have done over the years without Jimmy D there to reach around and slap his peepee when he gets dumb naughty ideas? Sometimes I watch other teams do seemingly retarded stuff and I think it's probably because some of these GM's don't have a Senior VP with 55 years in the NHL to check them when they're doing a stupid.
Jimmy basically transcended into the next plane of existence and became the guy who doesn't build hockey teams... he builds guys who build hockey teams. Ken Holland, Steve Yzerman, Jim Nill, Don Waddell. Those are all Jimmy D proteges who he mentored. And each one is in the upper echelon of GMs in terms of quality.
Now let's talk about his actual role with the team. He's alternate governor, which means he's basically governor. Chris Illitch is the true governor in name, but do you think he actually serves on the board of governors? No. He's not a hockey brain, and he has a $4 billion dollar empire to run, plus the tigers, and the family real estate holdings. He doesn't have time for this. And that's why he has an alternate gov. Devellano is his proxy and the true governor. Which is exactly why Jimmy is credited with a lot of improvements to the game, like the moving of the draft to the USA, moving it out of hotel ball rooms and into stadiums, 4v4 overtime, and the loser point. The guy is influencing hockey at a meta level.
Then the gritty level is... everything I've personally ever heard about the guy is that he sits in his office all day watching tape of hockey and baseball. He's said to have an obsessive level work ethic and is an extremely good judge of talent. Probably why he's basically one of the most successful scouts of all time. He called out Mantha's lazy BS before anyone else. Never doubt Jimmy D. Not only that, but he's also the guy who lobbied hard for Al Arbour in NYI and Scotty Bowman in Detroit. So not only does he know on ice talent, he knows other brains as well.
Now on to accomplishments. Jimmy has 7 Stanley cup rings. No one north of 1990 can hold a flame to that.
This is exactly the kind of guy you put in place to oversee operations. He's an executives wet dream.