If you have a decent team, you're never going to get a Crosby or McDavid via the draft, so you have to at least have the semblance of trying to put a contender in place every year to be attractive to the best free agents.
In my mind, attractiveness to free agents is a combination of performance and an explicit willingness to spend money to fix shortcomings. Babcock, Kessel and Phaneuf are not enough (in my opinion) to make the Leafs a legit contender. They need at least two more elite players (including a top 3 goalie) to make that happen.
Can you imagine what would happen if the Leafs won a cup? The heads of the over 4 million people in the GTA would probably explode. And right after that, you'd have massive spending on merch, etc.
Well yeah, that'd be great if they were in the MLB where it's a Luxury Tax instead of a salary cap. But unfortunately they're a hockey team, and so are in the NHL where there's a salary cap. You can't, by league rules, simply spend more than the cap. So how exactly do you suggest they "spend like Steinbrenner"?
One tool they can use is the Injured Reserve, which allows GMs to backfill a long-term injury with players of equal or lesser value without contributing to the cap. This is what the Leafs' GM Nonis used to free up cap space by trading Clarkson to the Blue Jackets for Nathan Horton, for example. And even then Clarkson had to waive his no-trade clause (which he was classy enough to do).
seems if the teams current woes are mostly due to poor managment, hiring the best (or at least best paid) coach is a pretty good start, especially considering that they apparently gave him an 8 year leash
There used to be - the financial goals of the Ontario Pension Plan (who owned a huge chunk of the team) ran counter to blowing huge amounts of money every year to increase the chances of winning a cup.
>> or is it simply a poor management issue?
Now that the pension plan is out, I think you can probably attribute the current state to a lot of bad decision making and not having a good long term plan.