Kessel is an elite offensive talent but he's a winger and you need an elite center or at least very good quality center depth to win Stanley Cups in the NHL. What's happening in Toronto isn't far off what happened here with Iginla and a bunch of 2/3rd line centers masquerading as 1st line centers. It's just not a good blueprint to build around a winger.
Jordan Staal is a 2/3 center signed to a #1 center deal. He's not good value at his current contract and he's always going to be a disappointment offensively.
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