An Untrue Underdog Story: Coping with the Imminent Rise of the Chicago Cubs

Joe Maddon introduced as new Chicago Cubs manager

Yesterday, ESPN baseball writer Keith Law released his yearly rankings of all 30 MLB farm systems. The team at the top of the list was one we’ve all heard plenty about this offseason, and I think I did the Steve Spurrier lips thing when I read their name. Law confirmed what I’d feared for months: the Chicago Cubs are going to be good very soon, if not immediately. And I’m going to have to get used to it.

I’ve never been the type to pick favorite teams. It’s been said–on this site, even–that most fans need a strong rooting interest before they can really settle in to watch a game. But when your allegiances aren’t predetermined by geographic location or bandwagonry, then you’re free to really relish the drama, quality, or even comedy that any sporting event has to offer. A walk-off homer is something to admired and savored, no matter what logo the hitter has on his helmet. Also, as a sports blogger who’s trying to write for a national audience (and failing – come on, North Dakotans, step it up!), I do my best to stay neutral. (Except when it comes to the North Dakota State Bison. May they never win a game again!)

When I was younger, words like “objectivity” and “emotional balance” were just piles of nonsense I didn’t understand. Though I was born and raised in Upstate New York, I was a Brewers fan. No one around me understood it, but a team that included the likes of Ben Sheets, Scott Podsednik, and Bill Hall was the clear choice. No, the team wasn’t very good, but I saw (or, more accurately, guessed) that better things were headed on down that big yellow slide in left-center field of Miller Park. A few years later, Ryan Braun and Prince Fielder had elevated the Brewers to annual contender status, and today, the franchise has effectively escaped its small-market torpor to become a well-attended and well-financed mid-market team.

Through all of this, the Chicago Cubs were either the Brewers’ biggest or second-biggest division rival, depending on the year, and whom you asked. While the Cubs had a solid hold on the head-to-head against Milwaukee from 2003-2010 (72-56), Brewers fans took cold comfort in their rival’s postseason defeats. The Cubs were a popular, large-market team, a fixture of the baseball establishment, and they still couldn’t win a World Series in over 100 tries.

I graduated from high school in 2010, went on to college, and didn’t have time to follow a baseball team with the same dedication I had in years past. The Brewers were no longer the lovable losers they had been before (Ryan Braun will do that to a team), and so I took a step back from them, just as I did with teams in other sports, as my desire to stay neutral grew stronger.

But I kept hating the Cubs, and still do.


I can’t stand their notoriously sloppy bleacher bums, their constant whining about curses and droughts, and their tendency toward building high-payroll rosters that simply do not deliver. Even the too-cute variation on their nickname–Cubbies–makes me want to send my fist through an ivy-draped brick wall. If fans of other teams started calling their clubs, say, “Cardies” or “Astries,” a lot of faces would get punched.

Admittedly, the Cubs’ tendency toward lavish spending had tapered off since 2012; they ranked 23rd in team payroll last year. They haven’t made the playoffs since 2008. You almost start to feel bad for them, but then you don’t, because they’re the Cubs. As hard as they try to embrace the lovable loser label, it’s not authentic. They cannot act out the role of underdog any more than the Yankees or Red Sox can embrace that role. It’s just a mask for organizational incompetence. They’re located in the third-largest American city, and they have a national fanbase. Yet they consistently get smoked in the standings by underfunded teams like Pittsburgh and Tampa Bay.

This offseason, Cubs GM Jed Hoyer hired bespectacled baseball wizard Joe Maddon to right the ship, and I fear a dramatic correction of course will actually happen this time. Even the team’s losing 2014 campaign had some bright spots; Anthony Rizzo and Jorge Soler proved their offensive worth, while Hector Rondon was a surprise midseason revelation at closer. And now the Maddon-led Cubs have buried a bunch of players in truckloads of money. Jon Lester’s making over $25 million per year until he hits his midlife crisis. Jason Motte’s on board, and even Jason Hammel came back after being whisked away to Oakland before last season’s trade deadline. Miguel Montero and Dexter Fowler were acquired via trades. The Cubs’ roster is a stacked one, and their minor-league system holds the promise of long-term success.

Part of me thinks everything will be okay. Hey, it’s the Cubs; they won’t win, right? But with such talent on both their roster and their coaching staff, it doesn’t seem like even the Cubs will be able to make a mess of this scenario for too long.


Sports fans with no rooting interest in a particular team tend to get behind the underdog, and I’m no different. Trouble is, the underdogs don’t win very often; it’s the nature of their role in sports. Still, it’s frustrating. Two borderline dynasties made the Super Bowl this year. LeBron James has at least another title or two coming his way. If I have to see Rafael Nadal bite down on another Grand Slam trophy, I might just lose faith in humanity (or, optimistically, just Spaniards).

So that’s why the Cubs have been fun to hate. They’re one of the big guys, with money, fame, and tradition behind them, and they’ve still been terrible. They’re like the trust-fund baby who blows it all on sports cars, yachts, and sports car yachts, and has to go to work at Carl’s Jr.

Only now, the trust-fund baby somehow got daddy’s philanthropist friends back on his side. I’m just hoping Jon Lester likes sports car yachts, too.