Every Stanley Cup team in the last decade or so has found themselves in salary cap hell shortly thereafter. You cannot win a Stanley Cup without taking on a few "bad" contracts, you just can't. To get some of the best players you need to incentivize them and sometimes that means an overpayment or a brutal term.
Look at Los Angeles, Chicago, and Pitt. 7 Stanley Cups between the 3 of them in 10 years and they're all in salary cap hell. The league is intentionally structure for parity, it's the most competitive major sport in the world. The reason that happens is that you pay a significant premium for being elite. You can be a "good" team for a very long time (Caps, Sharks, etc.) but I think the contracts that are anchors are often the ones that put you over the edge to elite.
We joke but in a lot of ways the Jackets have the right idea. Playing half in and half out doesn't typically yield results, also this league is so good at recuperating bad teams that unless you have intentionally destructive management you can go from cellar dweller to playoff team in the span of 3 years.