it's not that easy. If 3 years are up and McDavid needs a deal (2 years really), even winning the cup will not be enough. We need to be a team that is worth staying around for 8 years. That means we need to keep picks at the same time that we sell them off. For instance, thank god that Holland did not trade the picks that got us Holloway and Bourgault, and it was smart to roll with McLeod and keep Broberg. But, these will probably not be enough. When RNH, Ekholm, Kane, and Hyman age out we need replacements
There are other ways too. Holland has been pretty good at getting interesting free agents like college prospects, but we need to get some that hit, and to find late round gems as well. But, he's not magic. We need to keep some 1sts and 2nds imo