Full rebuild or try to remain competitive. One is like playing the lottery, one is a job to make rent every month. Just because Chicago is doing what they're doing, doesn't mean that in 10 years, they will have won anything. Look at Ari and Buf.
You buy that ticket though, and you get to imagine what that money could get you. But you can't start living the life of someone with millions before you have the winning numbers.
I would guess that Calgary knows it's a bad contract to give out, especially when the team, and the team + this specific player, haven't won anything. However, you have 41 days you have to sell tickets for.
This all or.nothing mindset is crazy. There's one champion every year. Look at the path Col took. You think there was a plan there? From drafting Duchene to this year was well.over a decade of constant ups and downs. They love Makar, but they weren't trying to be terrible 4 years after drafting MacKinnon, because it can only help to get more top 5 picks. Why win the Cup this year? Finish bottom 5 again, so that you have another great young talent. Guess who's going to cost more in the future? An ever aging MacKinnon.
And championship success is fleeting. We don't even care that the Kings currently have players that have won the only thing we care about, as Kings, still on the roster. Just have to chase the next high.
Stupid Calgary. Trying to not tank.