I would have to ask myself if this team is good enough to win it all. There are probably 6-8 teams every year that fits into this category. If I felt it was good enough (not today, but at the start of roster cut-downs), then I would have to ask myself a follow-up question: Is this team ready to absorb injuries, because they are coming. Every team gets them, and usually it is the team with the least, or the best depth that wins it all. If I felt it was not good enough, I would have to ask myself which players fit into the 3-year window, or if it was time to offload the aging players and start over (likely with a new coach and GM).
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