Hawks won 3 Cups. After the last one, they gave Toews and Kane massive (at the time) new deals. They haven't won since, and usually don't make the playoffs. At least with them, they actually won something before getting a big payday. Kaprizov wants a bundle after playing 55 games, and unlike Toews and Kane, didn't give the team much of anything during the ELC years, preferring to spend his time in the KHL. I think Guerin has to read the tea leaves here, and trade KK when he can get something decent for him. If he signs him forst, it's critical that he signs him for a contract that isn't considered a boat anchor, or he will be impossible to move.