Iginla want's to win a cup, even if he does win one this year I suspect he, like most hockey players would want to win it again.
Ignoring the fact that he likely hates the oilers now due to nearly 2 decades of hating them, why would he sign with the laughing stock of the league? Even if they offered massive overpayment, I'm sure a few teams that sucked just a little bit less would be willing to do the same.
I would be fairly surprised if he didn't sign a very reasonable contract with a contender regardless of if he wins his cup this year or not.
That said I look forward to the Oilers annual "We are good" talk followed by the fall in the standings that must set some sort of record for being terrible all the way to another lottery pick.
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