The Cubs Are Historically Great … And That’s Why They Won’t Win The World Series

I don’t want to be that guy. The one who looks at a team performing well above the curve of history and sneers with snide words like “overrated” and “deeply flawed.”

But I am that guy, despite my best intentions. The problem with the “Greatest Of All Time” type teams is that it is so astronomically hard for them to follow through on the expectations that get built up during the course of phenomenal seasons.

The race to quantify what a good ball club is going to in the grand scope of history —  in real time — becomes so dogged, so exaggerated, that it becomes nearly impossible for anyone, even under the best of circumstances, to live up to the billing.

So, I’m sorry Chicago Cubs fans. You’re going to have to wait ’til next year.


I love what the Cubs are doing. I love Theo Epstein. I love their cast of characters. And their brilliant manager. There’s not a guy in their lineup that I wouldn’t mind seeing in a Boston uniform (quite a few, actually, that I wish still were in a Boston uniform).

It’s not at all lost on me that they’re doing what they’re doing with 12 percent of their roster made up of guys who did what they did for the 2013 World Championship squad.

They’ve made a point to go out and get guys with playoff pedigrees to come alongside their budding superstars in supporting roles. They have a young core that rivals any club in the game (perhaps only superseded by Boston’s young group).

Truthfully, I don’t see them as “deeply flawed” but I do see inherent flaws in their strength of schedule, so to speak.

The principles of the great game of baseball simply don’t allow for teams to win at a 70 percent clip during the regular season and then push on to win the World Series.


Of the 14 teams to ever post a .700 winning percentage — EVER — only five slugged through the brutal postseason to win the World Crown.

Of those, only the 1998 Yankees have managed to do it since 1939 – when Major League Baseball had a total of 16 teams and none West of the Mississippi.

The 1998 Yankees were up against a very good Boston squad in their division (a division they won by a whopping 22 games). A good Toronto squad as well. They were a truly great team in a great division.

If you’ve read this blog at all, you know how important relative stats are to me – what every other team does against the teams the “great” teams are beating.

And that’s where the 2016 Cubs’ role in history breaks down for me. They are playing in a woeful league with seven teams below the .500 mark and three teams either right on the cusp of or below the .400 mark.

This year’s Braves on stumbling along toward one of the worst finishes in modern baseball history (although, in all fairness, so are this year’s Twins over on the AL side).

The Cubs can’t be held responsible for this – It’s not their fault the other teams in their league — particularly the division rival Reds — stink. But it also can’t be ignored that the AL appears, at least for now, more balanced. Cleveland, Detroit, Kansas City, Texas, The ChiSox, Boston, Toronto, Baltimore, Seattle. It’s a good, competitive league.

This year’s World Champion will come out of the AL. There is too much parity for it not to. And if I were a betting man, I’d say the champ is coming from the AL East.

I don’t like Boston’s in-division record, but I also don’t mind losses to the Orioles and the Blue Jays because it is shaping up as though this inter-divisional trio is truly the cream of the AL crop.

Someone will emerge there, through the brutal battles of July and August, and become the front runner. They may not come into the postseason with the best record in the league, but the best, most battle-tested team in the league, will come out of the East.

It sounds like a blatant bit of homerism, and I get that.

But baseball is a balanced game. Incredibly balanced.

Consider, since 2005 — an arbitrary starting point of what I consider to be the Money Ball era that has led to the rise of clubs like the Giants, Royals, Pirates and even the Red Sox — No World Series champion posted above a .636 win percentage (2009 Yankees) and nine of the 11 have finished in the .500s.

That’s where your champions will be – in the .520-.590 realm of tough divisions.

If there is an abundant disparity in win percentage, like we’re seeing in this season’s Cubs, it’s more of an indictment of the division than a credit to the team.

It’s just the way it is. And it’s the way October will prove it to be.



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