I have a problem.  It’s not a big problem.  It’s not even a real problem–more of a quandary.  But there’s a time limit on this quandary, and you good people might be able to help me make my decision.  Or at the very least, liven-up the decision-making process.

My conundrum: should I buy Cubs season tickets?  (Remember, not a real problem.)

Let’s begin with a little history.  I don’t remember when I first heard about the Cubs’ season ticket waiting list, but I’m pretty sure I originally signed up well over ten years ago.  I do know that it was so long ago the email address I used at the time–my college email address–is no longer even active.  The Cubs ticket office had to contact me by phone to get a new email address (and I’m not entirely sure how they got my current phone number, but that’s for another time).

In fact, it was so long ago that I had forgotten I had signed up at all, and signed up again years later with a different email address.  And if I log in to the Cubs’ wait list page with that second, current email account, there are more than 46,000 people in front of me in line.  Which means that if I pass on this current opportunity, more people than can fit inside Wrigley Field would either need to purchase and then surrender their season tickets or pass them up altogether before I’d have another chance to buy them myself.  When you add in all the current season ticket owners, and factor in that most people aren’t simply one-year-and-done when purchasing season tickets, it’s entirely possible that I could wait another decade before I make it to the front of the line.  And not altogether impossible that the opportunity might never come up again.

Now if I still lived in Chicago, there’d be no question about it.  But I live in Los Angeles.

(Like I said–not a real problem, but a significant quandary nonetheless.)

You see, if these were tickets I could use every day, or if I could split them with friends and attend even half or so of the Cubs’ home games, I’d have no qualms about buying them.  But if I plunk down the necessary cash for season tickets now, I’ll do it knowing that I can probably only hope for one or two weekend trips back to Chicago, at the very best.  I’ll wind up selling the vast majority of these tickets on StubHub.

And while getting some of that money back does make the initial investment a little easier to swallow, it also takes some of the shine off the purchase in the first place.

Now there is a chance that the Cubs could return to being relatively competitive next season, that tickets to Wrigley would once again be in demand, and that I could make back most of my money.  Possibly even enough of a profit to help pay for those trips back to Chicago.  But that’s probably wishful thinking, and it’s more likely I’d struggle to break even on the tickets I can’t use.

That’s most of the downside, as I see it.

The upside?  The Cubs will eventually be competitive again.  They’ll even get back to the postseason.  And as a season ticket holder, I’d have the first shot to buy playoff tickets.  And depending on how long I could keep buying the seats, I would potentially be guaranteed a seat in the bleachers when the Cubs finally return to the World Series.

Of course, I could also save all the season ticket money from now until then and have plenty of spare cash to buy scalped playoff seats on StubHub (possibly from some enterprising season ticket holder).

And sure, that’s a fine fall-back plan.  Heck, that’s been my primary plan for a while now.  But today, I have a chance to aim a little higher.  I have a chance to own a little piece of Wrigley Field.  (Probably a couple seats in the bleachers, because really, why bother sitting anywhere else?  Also, the closest seats are crazy expensive.)

For the moment, I have a chance to be a Cubs season ticket holder.

What would you do?

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