To be fair, Pittsburgh had Malkin at $9.5MM and were able to get Crosby under what looks like one of the last cap-circumventing deals. Dude was making $12MM and $11MM when they won their Cups.
Ovechkin at a $9.5MM cap hit but $10MM actual salary when they won the Cup.
Kucherov at $9.5MM but $12MM actual dollars last year. Stamkos at $8.5MM. Both of these are Florida tax sweetheart deals.
Mark Stone at $9.5MM on another no state tax discount.
I'm not saying that these big time contracts are poison but, yeah, you have to give them to the right players. The ones listed above are the right players or they take less because of the tax environment.
You do have to take in to account that nobody has had a double-digit AAV until the 2016 season with Kane/Toews, unless I am mistaken. So that is only five full postseasons + the current first round. There are only 13 double digit AAVs in the league so that also means that there are only a few teams eligible to even be a team that wins a playoff round with a double digit AAV player. Chicago was the only team in 2016 that qualified to do it. The 13 contracts are only spread across nine teams (Toronto has three of them). There are only eight teams each season that can win a playoff round.