Which Will be More Heartbreaking: Cubs's Postseason or Bears's Regular Season?

With Labor Day in the rear-view mirror, it’s time to focus on the shifting seasons.

And by that we mean the NFL regular season and the upcoming postseason for Major League Baseball.

Fans are busy breaking down the analytics, trying to prognosticate this year’s record for Chicago Bears or figuring out how far into the playoffs the Chicago Cubs will go. (Chicago White Sox fans, you can start thinking about the 2016 season or continue to wonder why the Southsiders put stellar reliever David Robertson on waivers recently.)

»RELATED: Should Cubs Solve the Case of the Buried White Sox Cap?

But the big question on the minds of fans sharing a love of both teams is also the scariest. It’s the question that considers the organizations’ past while attempting to tease out their future.

Which will be more agonizing and heartbreaking: the Cubs’s postseason or the Bears’s regular season?

Although the general reasons might differ, the idea that the following weeks will be fraught with soul-crushing disappointment are concerns for Cubs and Bears supporters.

Chicago Cubs

The Cubs currently have the second wild card spot in the National League locked up. But for the Northsiders to advance in the postseason, they must get through one of the cruelest of all the playoff contests: the one-game elimination. And the way things are going, it looks like the Cubs will be playing that game against the Pittsburgh Pirates, a team that has cultivated its own lovable losers reputation over the years.

Why the concern? If you’re not familiar with the Cubs’s history of curses and bad luck, not only are you not a true fan, you’re not even a casual baseball fan. Add that to the recent revelation that a White Sox championship cap is buried beneath concrete somewhere in Wrigley Field, and the Cubs are poised to raise the hopes of fans only to dash them, like Lucy yanking away the football at the last minute from Charlie Brown.

Chicago Bears

At the other end of Chicago’s sports spectrum are the Bears. They’re season begins Sunday with a home game against its mythic rivals, the Green Bay Packers. The Monsters of the Midway aren’t expected to do well this season (ESPN ranks them 25th in a 32-team league), and the season opener might be a microcosm of the reasons why. Green Bay’s quarterback, Aaron Rodgers, has not only been an unstoppable Bear killer over the years, he’s also shown Chicago what they lack in Jay Culter; that is a confident, unflappable signal caller who is adored by fans and elevates the game of those around him.

»RELATED: 5 Reasons Why Fans Love to Hate Jay Cutler

Why the concern? Cutler is the Anti-Rodgers on a mediocre team. Even a Pro Bowl-type season from him probably wouldn’t be enough for the Bears to rack up more wins than losses, especially in the tough-as-nails NFC North.

Of course, either franchise—or more incredibly, both—could give destiny the finger and overachieve. But those aren’t odds anyone should be betting the mortgage payment on.

So the question remains: Is it more disappointing to watch a competitive team snatch defeat from the jaws of victory? Or to suffer through a losing season by a miserable team?

YOUR TURN: Which will be more heartbreaking and disappearing, the Cubs’s postseason or the Bears’s regular season? Share your thoughts and opinions in the comments section.