Chicago Cubs: The 5 Worst Moments in the Team's Tortured History

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Chicago Cubs: The 5 Worst Moments in the Team's Tortured History

As a Reds supporter, I love talking to Cubs fans.

See, in Cincinnati, we’re used to losing. We’re familiar with the bruised, aching feeling that follows every season gone bad. We know all too well the dejection of finishing fifth or sixth in the division, with no realistic prospects of hope on the horizon.

Yet, no matter how low a team like the Reds sinks into the vacant, hollow abyss of obscurity, it helps to know that there are Cubs fans out there whose plight makes ours seem like a paddleboat ride down a chocolate river. I know a few guys like this. So, luckily for me, whenever I’m in need of some grounding, ready to fire my fan-hood right into the toilet bowl, I know who to call.

These guys have spent their life in the pisser, and can tell you exactly how it tastes.

Now, there are certain areas in the sporting world where we dare not tread lightly, without deference to their importance or reverence to what they have meant.

The ineptitude of the Cubs is one of them.

Therefore, when asked to create a list of the worst moments in Chicago Cubs history, rather than compile a stale list of dates and names, I decided to reach out to genuine Chicago faithfuls for some meaningful commentary. Guys who, either through our family, school, or work relationships, have exhibited precisely the level of bile I expect out of Cubs fans. Sick to their stomachs, jaded to their core.

I reached out to all the Cubs fans I knew and, though responses varied, I wasn’t surprised to get the most scintillating stuff from my "uncle" Pete. A family friend, lifelong Chicago resident and business owner, and Cub-cynic extraordinaire, Pete used a series of e-mails to illustrate the steaming pile of dung that has come to define Cubs fandom. With vigor, he was happy to enlighten me on the lowlights of his proud, tortured tenure.

What follows are the worst in a long succession of sordid Cub moments, with agonized commentary from the biggest Cubs fan I know. 


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