I play a lot of fantasy sports (which I'll explain shortly after the fold), but I don't usually gamble. I mean this non-controversially: I almost always don't play fantasy for money. I have ventured into playing for money a few times, but I tend to get worse at it. Usually, I make mistakes based in risk aversion, like taking a quarterback early, maybe even second round. I know, you are already wondering: And they let him teach philosophy??? I know. The money screws me up. That's why I almost never play for money. I will say, when not playing for money, I have won more than a few ships.*
*By using "ships" instead of "championships," I am signaling that I'm cool/hip/with it.**
**By (a) blogging, (b) having footnotes in my blog posts, (c) having footnotes within my blog footnotes, (d) explaining what I mean by "ships," (e) not knowing which term to use for "cool," and (f) pretty much everything else about me, I'm signaling I'm not cool/hip/with it.
But now there's a question of whether daily fantasy counts as gambling, and I think this is a rather interesting philosophical question, which is worth exploring a bit.