Do I want — really, actually, genuinely want — the Cubs to win the World Series? It’s a question I grappled with at length after a couple whiskeys with my best friend from back home as they marched toward the pennant. I love the Cubs. I’ve always loved the Cubs. There is little else (some humans excluded) I love more than the Cubs. So what’s my problem, anyway?The Awl addressed the paradox with a cautionary tale from a Red Sox fan: “Without all the losing, the Red Sox are now just another pretty good team. The aura of mythology that swirled constantly around them was gone.” And that’s a big part of it. Losing is what the Cubs are known for. But we bleed-blue fans don’t root for lovable losers for the sake of it. We don’t do it because we’re proud of the title drought or miserable seasons. We don’t happily bask in the black-magic glow of curses or take masochistic joy in the outstretched arms of Bartmans.We root for them because eventually they will win, they just have to! It’s math! Curses aren’t real! And when they do win … my God, it will be ecstatic bliss. Angels will sing. Fathers, sons, mothers, daughters will sob tears of joy. Bill Murray will be there. Etc.The question is when do we want to cue the messianic chorus. Maybe Cubbie fandom is something like holding an American option — a piece of paper we Cubs fans carry around in our pocket and turn in at the bliss counter one day when they Win the World Series. In exchange we receive some number of singing angels. The longer this takes — the more heartache we bank — the more angels. That’s just math, people. If the Cubs had won it when I was, say, 3 years old, the rest of my fandom wouldn’t have been imbued with a greater, Sisyphean meaning. So, on my deathbed, yes, I should want nothing else than to cash in. If I’m watching from my high chair, I’d probably like to wait a while. To bide my time until 8:08 p.m. Eastern on Wednesday night, I hastily sketched a chart of how my 31-year-old self should weigh these priorities, complete with an “exercise boundary” that tells me when I should want the Cubs to win so I can cash in my pain for those angels. So what does my analysis reveal? Will I be rooting for the Cubbies? Of course. I just can’t not. In late October, math no longer applies. Share on Facebook You’re reading Back of the Envelope, an experiment that aims to bring shorter, quicker content to FiveThirtyEight.