I don't think money will end up being the deciding factor for Gaudreau. He's going to get paid no matter what. It is what else the team is going to offer him and his family that will ultimately decide where he wants to spend what could be the rest of his career. He's comfortable playing here, so there's that. However, he probably wants to win. Therefore, this year's playoffs will have a huge impact. I would put the resigning odds at different levels depending on how the team does this spring:
25% 1st round exit
40% 2nd round exit
60% 3rd round exit
75% 4th round exit
85% win Stanley Cup
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