Depends entirely on ownership and what they let him get away with.
Good:
- knows how to spend money if the owner allows him to
- Can attract executive talent if given the biggest platform in hockey and the ability to spend more than everyone else
Bad:
- Slimy politician that fades away and reappears whenever it's convenient, and will do anything to preserve his spot
Ugly:
- 0 asset management
- 0 talent assessment
- Unable to make ANY difficult decisions
- Unable to win any contract negotiations
- He will make statements like this:
Citing his old Red Wings team as an example, Leafs president Brendan Shanahan suggested some financial sacrifices that players like William Nylander, Mitch Marner and Auston Matthews could make to stay together and try to help the franchise finally achieve something special.
www.tsn.ca
And then follow it up with the worst contracts and selfish loser culture you could ever imagine
- Tried reinventing the game of hockey and provided nothing but the most embarrassing moments year after year while looking down his nose at everyone who dared question his Square Wheel Anti-Hockey Theory
- Wasted almost a decade of time and irreparably damaged the franchise
Overall? When the stakes are low and given an open checkbook he is able to surround himself with the most bloated executive team in hockey and is able to tank (congrats?). When it comes time to actually build and develop the team, and reap the rewards of tanking then the knives come out for anyone that disagrees with him and the team becomes a Yuppie Stasis Chamber where you see your favourite players walk out the door for nothing and the most gutless losers you've seen in your life put on a pedestal over all-time legends that are pillars that the franchise and league were built on.
But maybe he'll be better for the Islanders.