How to decide if you're an Indians or Cubs fan for the World Series

This might be the best World Series matchup you will ever see. This is not hyperbole. This is not a drill. If you think too much is being made of this pairing, you’re completely allergic to baseball history. And that’s fine. I almost envy the ability to enjoy a baseball game on its own merits, without a need for prequels or prologues or suggested reading.

For the rest of us, though, this is an absolute hallucination. A Cubs vs. Indians World Series. What a world.

The Indians, man. They were the team in Major League, a story about unfathomable losers who were hand-picked to lose on purpose. When it came time for the happy ending, the writers had them win the AL East, not the World Series. Because Hollywood has its limits. There needs to be at least a little suspension of disbelief. The last time they won a World Series, Satchel Paige was on the team and they beat the Braves, who played in Boston.

The Cubs, man. They were the last team left that could call the Indians a bunch of whiners. The Indians have won a World Series since the last time the Cubs even won a pennant. Morgan Freeman, Dustin Hoffman, and Jack Nicholson were 11 the last time the Indians won. If any of them were paying attention, they might still have a memory or two. No one remembers the last time the Cubs won because memories hadn’t been invented yet.

You are an impartial observer. You like to watch teams win that haven’t in a half-century or two. And usually there isn’t much of a decision to make. It’s usually the Cardinals vs. the Washington Generals, and you root for the Generals, even though you know they’re going to lose in a horrific fashion.

This time, though, you need help. Are you rooting for the Indians or Cubs?

We’ll do our best.

History of pain

So the Cubs haven’t won in at least a decade, but I’m going off memory here, so forgive me if it’s been sooner. However, the Indians also haven’t won in at least a decade. What to do, what to do?

After looking it up, wow, this is wild. Are you ready for this? The Cubs haven’t won a World Series in 108 years. The Indians haven’t won in 68 years. That’s a 40-year pain gap, with the obvious edge going to the Cubs. There are, again, living people with specific memories of an Indians World Series.

At the same time, those people are old. Really, really old. And if we can get wistful for a team like the Royals winning for the first time in three decades, that applies twenty-fold to the Indians. The difference between 68 and 108 years is negligible for me.

Me: Sorry, but I just can’t care as much about your seven decades of pain because of how happy you must have been.

Incredibly old person: (weakly) I have so much pain in both a metaphorical and literal sense.

Yeah, it’s a virtual tie for me, at least when it comes to the actual World Series part.

Ah, but there’s a tiebreaker. Winning the pennant is, in fact, really, really fun. There’s a very specific kind of heartbreak waiting for one of these teams, but that doesn’t take away from the initial rush. We’re going to the World Series. Just the thought is enough to power a city grid.

The Indians have won two pennants in the last 21 years. That doesn’t ease the pain of not winning a World Series, but it’s a heckvua lot more than the Cubs have over the last century

Advantage: Cubs

Likelihood of making you feel stupid for ever rooting for them in a few years

We’ll call this The Sox Conundrum. When the White Sox went to the World Series in 2005, they were facing the Astros, who had a much shorter, but still very real, legacy of pain. When the White Sox won, Astros fans could think, "This stinks. But at least they haven’t had one for a while. Let them have one, I guess."

And they were right. That championship is still the crowning glory of the White Sox, who hadn’t even won a postseason series since 1917 before that World Series.

However, on the other side of the aisle, we have the Red Sox. You felt pity for them in 1986, right? Or how about 2003? Hard not to empathize. Imagine feeling pity for the Red Sox now, though. You cannot. They’re firmly established bullies with three recent championships. They crushed the hopes and dreams of another never-won, the Rockies, for their second championship since 1918. And while I approve of their organizational philosophy of making the Cardinals sad, it will be another 50 years before they’re even close to endearing again.

The odds are at least decent that you were rooting for the Red Sox in the '04 World Series. You can’t mask that stink with some perfumy lotion, and now you’re stuck with it for the rest of your life.

This is the danger of the Cubs. They are so good. They are so young. They play in a market that’s as big as the rest of the NL Central combined. We might look back in a decade and say, "Remember when we wanted the Cubs to win?"

I remember a Giants/Red Sox series in 2007 at AT&T Park that was absolutely saturated with Red Sox fans. And they had the look. The technical term is "the neener-neener look" and it made me so jealous. They actually had hope that good things could happen to them. Disgusting.

Beware of the Cubs. The Indians’ window isn’t exactly closed right now, but beware of the Cubs. They seem adorable, but they will rip your face off.

Advantage: Indians

Real-world stuff

Don’t spend too much time on this one. The Cubs are entrusting their leads with someone who’s probably an unrepentent goblin. The Indians wear uniforms with a remarkably hideous and racist caricature. I wish that neither scenario were true.

If you attempt to quantify the harm of both, though, you’re trying too hard to look for the missing water from the half-full glass. Think of the fans, the millions of good ones who have invested decades in these teams, tens of thousands of hours, and imagine just how happy they’ll be.

Or if you’re as misanthropic and cynical as I am, think of the thousands of good fans.

Hundreds at least.

OK, there’s Phil the Indians fan, and he’s fine enough, I guess, and Samantha the Cubs fan, and she really is selfless and amazing. Think of them.

Advantage: Tie

Underdogitude

This is from a pure team strength perspective, and it’s pretty clear that the Indians are favorites, even if the Cubs made the mistake of starting Johnny Cueto in the All-Star Game and giving away home-field advantage. The Cubs are the best team in baseball.

They’re at mostly full strength, too. We looked at which postseason teams had the most reason to be disgruntled with their injury luck, and the Cubs ranked near the bottom with Kyle Schwarber out, whereas the Indians took the top spot, with two of their big three starting pitchers out. Danny Salazar and Carlos Carrasco still haven’t appeared in the postseason, and since they went down, they were joined by the Indians’ fourth starter, who was bitten by a machine with a taste for human flesh. The Indians have a chance to win their first World Series in decades, and they’re a) going up against an exceptionally strong team by historical standards, and b) without three-fourths of their rotation, which was the biggest reason they won the AL Central in the first place.

And now we’re getting word that Schwarber might make a surprise appearance after all. That would mean the Cubs are almost entirely healthy. I can’t think of a World Series winner off the top of my head that didn’t have at least one significant injury.

The Indians are already the Indians, and against literally any other team in baseball, they would have the advantage when it comes to the legacy of pain, so it’s almost cruel that they’re not the clear sentimental favorites in this World Series. But they’re certainly the clear underdogs, and they’ve fought through far more adversity in this season.

Advantage: Indians

Is Adrian Beltre on one of these teams?

No. Dammit.

Advantage: Tie

But Andrew Miller is, right?

Damn straight. So let’s make this the fun-to-watch category. Is there a way to root for one of these teams based on the entertainment quality of the players involved?

Miller is a slider titan from underneath the Earth’s crust. There might not be a pitcher who’s more fun to watch.

Francisco Lindor is a two-way marvel who can do everything. It's a shame that there isn't a camera trained on him at all times.

On the other hand, Javier Baez sure is a delight. Anthony Rizzo and Kris Bryant are the superstars the Cubs have been waiting for since Sammy Sosa.

Jake Arrieta and Corey Kluber share the same comic book origin story, and I'm half convinced they're the same pitcher. Both are extraordinarily fun to watch.

Jon Lester is a delightful baseball craftsman. Jason Kipnis is, too. Mike Napoli hit ball hard with stick. Kyle Schwarber hit ball hard with stick.

These are both dynamic, fun teams. Which I suppose most pennant-winning teams are by definition. These two teams especially qualify, though, especially with Terry Francona's willingness to use Miller whenever appropriate.

Advantage: Tie

Conclusion

You didn't need this rooting guide. You already have your team picked out, and you're not veering from that path now. Maybe the Cubs' 108-year is the only factor you need. Maybe it's one of those real-world concerns up there. Maybe you're a fan of a team in the NL or AL Central, and the Cubs and/or Indians just bug you.

As for me, I've been rooting for a Cubs/Indians World Series for, oh, 20 or 30 years now. And that's the only rooting interest I can possibly imagine. Of all 25 potential World Series pairings, this was easily the best one. The problem with it is that this guarantees just about the most painful ending for one of these teams. They will be all alone at the top of Sad Mountain, and they'll have to attend cocktail parties with teams like the Padres and Mariners, who will think they're peers, even if they have no idea.

The only thing to root for, then, is a clean series. No goats. No errors. No controversies. Just one team playing that much better. Both of these teams have had their hearts pulled through their noses in the last two decades. Don't allow that to kind of misery to happen again. Not to one of these teams.

Just one sturdy kick to the heart, over and over again when the memories appear unbidden over the next several decades, will be more than enough.