Chicago Cubs: Painting a picture of your very worst nightmare this winter

You might think missing out on Bryce Harper is a worst-case scenario for the Chicago Cubs this offseason. But I’m here to tell you it could get worse.

Chicago Cubs fans are hardly known for being a group of optimistic individuals. In fact, quite the opposite is true – we are downright pessimists, always waiting for things to break the wrong way, for an unsuspecting fan to snag a foul ball down the line or for a black cat to scurry past the on-deck circle at Wrigley Field.

Those days are over – thankfully. It’ll take some time for us, as a group, to move past, well, the past and accept our new reality. What reality, you ask? One where the Cubs have won more regular season games than any team in baseball over the last four years and have reached the postseason annually since Joe Maddon took the reins in 2015.

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But that’s not to say this Golden Era of baseball on the North Side will come without disappointment. In fact, the opposite has already proven to be the case. After winning a World Series championship, losing in October tastes more bitter than ever. When the team makes big acquisitions and there’s no instant gratification (Yu Darvish, Tyler Chatwood) – fans get angry.

You think this is bad?

Again, it could get worse. It seems like everyone I run into on the streets is ready to go out and buy a number 34 ‘Harper’ Cubs jersey ahead of Christmas. And while you might think missing out on Harper is the end of the world, it could be worse.

Just imagine – what if he came to Chicago? But I’m not talking about an introductory press conference at Wrigley Field. Instead, he puts on a black and white pinstripe White Sox jersey in front of the South Side media at Guaranteed Rate Field after signing a 15-year contract to finish his career as the face of that franchise.

Nope – not even that is the worst-case scenario. And, believe it or not, it doesn’t involve the St. Louis Cardinals. Why? Because I can honestly say there’s next to no chance Harper spends the rest of his career anywhere but a major market – something St. Louis doesn’t exactly qualify as, especially alongside the likes of Chicago, San Francisco, Los Angeles, New York or Washington, D.C.

The only way something like that would happen? A team drastically overpays. And I trust Cardinals management to not do that. They proved their willingness to let major players walk back in the day with Albert Pujols. And, while the situations are different, such a signing doesn’t fit that front office’s M.O.

This? Yes, this is bad.

One team, that could blow the lid off the National League, though? The Milwaukee Brewers.

In at least one report, the Brewers have been labeled as “a perfect dark horse fit for Bryce Harper.”

That, my friends, is the worst-case scenario. Because so many things would have to go wrong in the Chicago Cubs world for such an instance to become reality.

It means ownership (I’m looking at you, Ricketts) let themselves be outspent, despite soaring revenues from Wrigley Field and the surrounding area. There’s no way this should even be remotely feasible and, for the record, I don’t think this is how things play out.

Not to mention, we’d be dealing with Harper playing for a division rival for years to come and undoubtedly becoming the latest addition to a long line of Cubs killers who haunt us in our dreams. He has a career 1.106 OPS at Wrigley Field. So, no thanks. I don’t need to see him with a division rival.

And lastly, it means that somehow, Milwaukee outbid the likes of the San Francisco Giants, Chicago Cubs, Washington Nationals, Atlanta Braves, Philadephia Phillies and Los Angeles Dodgers and (for argument sake) the St. Louis Cardinals.

Next. Mariners, Cubs make a lot of sense on paper. dark

And therein lies why this won’t (at least that’s what I tell myself) happen. If Milwaukee managed to outspend all of those teams, it would mean financially crippling the organization for years to come. Sure, you might have Bryce Harper at Miller Park. But you wouldn’t have much else after Christian Yelich and Lorenzo Cain leave town in a few years.

Thank goodness.

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