How a $500 Cubs Bet Got Me To Like Baseball

Two years ago, I made a really dumb bet. Like…really dumb. I bet my friend, a lifelong Cubs fan, that the Cubs wouldn’t win the World Series within the next 20 years. I confidently put $500 dollars on the line, shook hands, and thus cemented myself as one of the worst betters of all time.

Granted, I’m not a baseball fan. There may have been several (read: many) beers involved. Still, I thought it was a great bet! Even as a non baseball fan, I knew the saga of the cursed Cubs. They were the poster child of failure, failing to win a championship for over 100 (!) years. They were the lovable losers, perpetually putting their loyal fan base through the ringer. As an Arizona sports fan, we’ve had our fair share of heartbreak and failure. Still, our inept franchises weren’t even in the same stratosphere as the Cubs.

I never much cared for baseball. I know, I know. Hating on America’s past time is downright sacrilegious. All the ballpark Frank’s, seventh inning stretches, and first pitch blunders are ingrained into America’s DNA as much as… I considered myself a proud cynic, a member of the growing counterculture with anti-baseball sentiments.

The game is too long. It’s boring. Nothing exciting ever happens.

For me, baseball was just another nod to the older generations “good ole days.”It was the sport my grandpa loved – the same guy that seeks thrills through yard work. Sure, I cheered for the Dbacks in 2001 when they beat the Yankees and brought my hometown its only major sports title. But that was the blind cheering of a 10-year-old. I cheered for them the same way I cheered for brunch for lunch in the cafeteria on Fridays.

So when last year’s playoffs came around, I was forced into becoming a casual observer of the sport. I watched not as a fan but from a pure financial standpoint. Though there were a few scares, the Cubs eventually fizzled in the playoffs. Baseball was out of my life and I was free to spend my time over-analyzing my fantasy football team. Life was good.

Then came this year. The expectations were higher for the Cubs but I remained unfazed. That just meant the surefire collapse by the Cubs was going to be that much sweeter. Then they beat the “Even Year” Giants, the hated Dodgers, and reached the World Series. It was finally time to take them seriously and (shudders) watch a baseball game.

Game 1 was a blowout for the Indians. Game 2 for the Cubs. I sweat, prayed, and bartered with the sports gods. But I still watching from a purely financial standpoint. It wasn’t until Game 3 that things began to change. Every pitch, swing, and hit was amplified.  You could feel the tension from Wrigley field seeping into your living room. The entire world seemed to be zoned in on the Cubs but the Indians wouldn’t relent. It was a back and forth pitchers duel with the weight of two long suffering franchises hanging in the balance.  As the game closed to a 1-0 victory for the Indians, all I wanted to do was watch four. Something had changed – I actually wanted to watch a baseball game.

By mid Game 5, I was a wreck. The Cubs had rallied behind Kris Bryant’s homer and were not going away quietly into the night. My Snapchat, timeline, and Twitter all revolved around the game.  Heresy! This time of year was reserved for NFL & NBA highlights. Yet here I was, enthralled by a baseball game and not giving a shit about anything else. What the hell was happening to me?

Then came game 7. Almost 15 years to the day since the Dbacks squared off against the Yankees in a game 7 for the ages.  Just like when I was 10, my stomach was in knots, my heart beat dangerously fast, and I couldn’t control my emotions. The epic comeback, the rain delay, the emotionally damaged fans. For a moment, I was brought back to that last moment I truly cared about baseball. The game ended, the Cubs were victors, and I lost my bet.

The last week and a half cost me $500, bragging rights, and most of all, my baseball cynicism. That drama filled series was for lack of a better word, a gamechanger. I’m not sure that series will fix all of baseball’s problems. But for a brief time, baseball was king again. Even if you weren’t watching the game, shamed into doing so by your friends on Snapchat. Hell, from my Facebook feed it appears I’m the only non-Cubs fan left in the world. That series is what everything I wanted from sports, and I might just be watching next October.


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