If you recall just a few years back as general manager of the Edmonton Oilers, Ken Holland said arguably his most infamous quote "I don't think that you can be all-in every year. I think you pick and choose."
This quote encapsulates his tenure as GM of the Oilers well, refusing to do what is necessary to win a Stanley Cup, instead there were plenty of half-baked solutions where instead of dropping multiple picks and prospects on acquiring a big fish, he attempted to shore up the depth.
This conservative approach can be useful in some situations but we would not be here today, only a day after franchise player Connor McDavid signed only a two-year commitment, if it was successful.