As a lifetime hardcore leaf fan, I would give up almost any amount of money for it. I am happy with my life, if I suddenly came into some money that I wasnt expecting I would most definetly give it up to see us win. There is no dollar amount that would change my mind. The cup would be the greatest thing that could happen in my life, money isnt even close.
But in all seriousness, if you're a diehard fan of a team, then you've devoted several hours and emotions of your life to that team (and most likely money as well if you've purchased tickets, merchandise, etc.)
I think the feeling that you'd get from them winning the Cup would be much more gratifying and long-lasting than what $2000 will get you.
Several hours??? ... try 20 years and counting and I'm not even close to some Leaf fans out there.
That depends. First, if I found that kind of money, I'm going to try and give it back to whoever lost it. So, unless it's Bill Gates that dropped it and he tells me to keep it, that money is as good as gone.
Second, if we're talking the Red Wings and if it's gift money, I'd rather have the money. It'd be nice if I saw a 5th cup in my lifetime, but the first 4 were good memories enough.
If we're talking the Caps who have never won, then yeah, the cup.