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Ruminations on the Cubs finally winning a World Series

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The task was already tall for the White Sox, but now it's a little taller

Justin Merriman/Getty Images

It was never going to be easy for a lot of White Sox fans to swallow a the first Cubs World Series title in 108 years, but these might’ve been the easiest circumstances to deal with it — a gut-wrenching extra-inning Game 7 against the Indians, which for Sox fans is an uneasy alliance.

This game could’ve effectively ended with David Ross’ home run to unload an avalanche of saccharine Grandpa Rossy drivel, and it could've actually ended with Aroldis Chapman closing out an extended save to receive some unearned redemption. Instead, Joe Maddon had to sweat out his terrible managing when Rajai Davis tied it up, and we ended up getting a legendary ballgame regardless of the teams. I’m surprised how much I enjoyed a game I didn’t really want to watch.

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I have a few good friends who are good Cub fans. One of them is Randy, and I sent him a text simply reading, "It’s happening." I had stepped away from the game and thought it had extended into the ninth with a three-run lead, so I treated the response ("Inappropriate. Thought you were better than that.") as typical drought-induced hand-wringing.

Then I got back to it in time to see Davis homer aaaaaand ... heh. Again, it speaks to the power of the game that I was surprised that I felt slightly bad. I then shut up until after the final out, after which I texted, "Never a doubt."

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The drought was going to end at some point, and being in Chicago for the suffocating media overload during the NLCS, the most realistic alternative — at least a couple more runs within the next five years — was only going to prolong it. There’s some advantage to ripping off the Band-Aid.

There’s also this ...

... which brings to mind the Golden State Warriors, who won over the country’s collective hearts by snapping out of their franchise’s doldrums with likable stars who had just emerged with an exciting style of play.

A year later, the Warriors were the ones being roundly mocked for blowing a 3-1 lead in the finals to the Cleveland Cavaliers (which Indians fans were reminded of time and time again). A lot of things contributed to it — more detectable arrogance from their backcourt and ownership, Draymond Green’s groin shots, begrudging admiration for LeBron James — but as Grant Brisbee noted, it wasn’t going to take much to flip the script.

I imagine Cubs fans will face the same fate. We saw it with Boston -- the easy underdog story is gone, replaced by obnoxious bandwagoners who take over road stadiums, celebrities glomming on to cash in, and a media that recycles the same fawning coverage. The Wrigley scene that fatigues even the ambivalent White Sox fan is going national. Good luck containing that. Even Bill Murray might not be immune from it.

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But those are great problems for a franchise to have. They’re better than the White Sox’ problems — a franchise that’s perpetually stuck between competing and rebuilding. This year hurt more than most, as they ruined the concept of a hot start for the foreseeable future, then finished it by hiring another manager without an interview process and giving their stadium a worse name. Now?

Here in New York, baseball fans ask me if the relationship between the Sox and Cubs is akin to the Mets and Yankees. I tell them it’s worse for the underdog in Chicago, because at least Mets fans understand why the Yankees get top billing, what with the 27 titles. The Cubs grew in popularity by failing, which makes it all the more aggravating.

Now, the Cubs now have a legitimate accomplishment to celebrate, which makes the imbalance understandable. Perhaps that'd be a positive development if it didn't wipe out the last vestige of South Side bragging rights that packed a punch (I don't think the Crosstown Cup counts anymore, gang). The Sox might have a higher percentage of "real" fans and a less nauseating scene, but that rings hollow. Sports are entertainment above all else, and one side of town is making it look way more fun than the other, and not just by drinking.

Moreover, a sustainable Cubs run pretty much cancels out all gains made by the White Sox in 2005. The Sox had briefly cornered the market on impressionable fans -- you know, second graders and John Cusack — but they’re back to relying on family ties and young iconoclasts. In other words, it’s back to being what it was, assuming it was ever truly different.

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Now we’ll see how the White Sox respond, although the response won’t be prompted by the outcome of Game 7. It’s all a reaction to their own irrelevance, which was already a problem the team had to confront. A Cubs title merely puts it in starker relief.

For the time being, they have to be gracious.

And the Chicago baseball aspects of it did register to me through this process. Learning about baseball history growing up, I was extremely confused that neither Chicago team had won a World Series in the live ball era, while all these other cities found a way to break through regularly even with one team. For all I know, the collective drought might've been the first time my brain could register "pitiful." If you are the rare Chicago-first baseball fan, self-respect is increasingly easier to find.

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On the South Side, it's more difficult.

As we’ve spent the last month or three discussing, the franchise already has to pick a lane this year, spending like they mean it or packing up and selling off. Either one is defensible, and with the Cubs showing one way to rebuild, a teardown is more palatable than ever. History says they’ll make one more run at it with their core, but history also says they’ll pull up short of truly supplementing it and instead will be forced to rely on almost everything breaking the right way, which probably won’t with the way their pro scouting has turned out.

But hey, one team was able to upend a far heftier history, and with impressive efficiency. It just needed somebody to aggressively pursue external solutions to address and revamp what hadn’t worked for years.