It's really personal preference. You're losing money long term if you were to hedge with the Cubs. However, unless you're someone that frequently makes series bets, that doesn't factor in so much. Not everyone will agree with that line of thinking because you are lowering your expected value regardless of how many times you're put in this situation to decide whether or not to hedge a future. It really comes down to your own preference for riding it out (and taking advantage of the great value you've bought) or taking a no loss/guaranteed money position (but at the same time lowering your expected value). Weigh those 2 things and cap the game, that'll lead you to a decision.