Not even $11M UFA's ? huh, imagine that.
The Tavares contract is a problem, but at this point it's basically unmovable and is water under the bridge.
It deprives the Leafs of a lot of salary-cap flexibility that they could really use to improve the team, and at this point all they can do is manage around it, which they are doing.
Whether it was a wise move at the time the contract was signed is a whole other issue without a clear answer.
It was certainly very aggressive and perhaps short-sighted to lock themselves into a high-dollar long-term deal for an aging player, and this would also apply to other teams with other players such as Vancouver's Miller etc. There's plenty of reason to think it was a bad choice from the outset.
On the other hand, it might have been reasonable to think that the salary cap would rise over the life of the contract, making it more affordable in relative terms. I think also the inexperience of Leafs' management at the time may have lead them to be overly optimistic on the potential costs of re-signing their other star players, which certainly factors in the equation every bit as much as the stagnant salary cap. However, the Tavares signing did signal a commitment to winning, and it lent much needed credibility to the Leafs' franchise which had never been able to sign significant free agents, even among those from the GTA and Southern Ontario.
On the whole, it turned out to be a mistake, but it wasn't necessarily so from the outset.
Hopefully, once bitten, twice shy.
BTW -- I also have great discomfort with the constant trading of futures for TDL help. I don't think any of the players they've acquired are worth the price they've paid -- including O'Reilly and the whole lot of them. I would much rather see the Leafs continue to develop, getting better year-by-year until they are perennial champions. I don't think you do that this way.