We all have different priorities, and are all wired differently. Personally I'm old school and would play in the NHL for a team jacket, if I had the chance to win a SC.
Assuming Holloway has a decent but not spectacular career, he should be able to 20M over his career. With this deal he adds a couple of million to that total, say 22M. As a player, what monetary value would you place on being a SC champion? For me personally, it would be a lot, especially if I had the career earnings I expect Holloway will end up with. I would easily give up 2M to have a lifetime of memories as a SC champion, and still have made 20M. (And I get that there is no guarantee he will pan out and make that money, but I think with his talent and the way the cap is heading, that is a reasonable number, maybe even too conservative.)