Too many people here have the mentality of a 10 year old lol, winning a Cup is cool but if you're not a major part of the team no one cares that much.
If you had an agent and/or wife-fiance, they would slap you upside the head 50 times and tell to choose HHOF career.
Being a nobody on a Cup team is not worth throwing probably in the range of $60+ million in career earnings down the toilet.
Even Cup winning teams don't give a shit about small time role players on their teams, they discard them all the time as soon as the off-season starts.
There are plenty of guys on Cup winning teams who are playing in Europe or out of the NHL within 1-3 seasons.
I get a Cup being important to someone who's been in the league for a while and is financially set but if you're not financially set, choosing a Cup over multi-generational wealth (if you invest even reasonably well) is dumb as bricks.
Being a HHOF player also means you have it made with a post-career in hockey if you want. You can become a sportscaster on Sportsnet, TNT, ESPN, you can work as a scout, coach, assistant GM, GM, POHO, work for the NHL, etc. etc. etc. All kinds of doors are open to you for life basically if you want. If you're a role player on a Cup team from like 20 years ago ... guess what? No one gives a shit about you.