What's the REAL reason the Cubs haven't won the World Series in so long?

Former Sox fan here (don’t get me started on what’s wrong with baseball today) but there is a history of the team written recently the premise of which is the Cubs win when they aren’t owned by a corporation. I don’t know who wrote it or the title, I vaguely remember the interview on Chicago Tonight within the last 4 years.

In fact there were far fewer than 30 teams for much of the 104-year period. Doing the math correctly, the chance of a 104-year drought = only 0.44%.

However, the more telling statistic is to count post-season appearances. Taking into account the varying number of teams in the playoffs, the Cubs expected number of playoff appearances since 1908 = 16.17. The actual number of appearances = 14.

So, only slightly below average.

Why haven’t they won it all? Because of an extraordinary run of 13 defeats in 14 post-season series (the exception being versus Atlanta in 2003). In other words, bad luck.

Other than the World Series, I don’t think there were any playoff games before 1969. 1969 was when the two leagues split into divisions, necessitating playoffs between the division champions. (There may have been playoffs if there was a tie for first at the end of the season, I don’t know if this ever happened.)

Or maybe I’m remembering wrong?

I should have said, 14 defeats in 15 post-season series. Since they won one in 2003, they played another that year. They would have won that one, too, except that their shortstop made an error and Kerry Wood pitched like shit.

Something else weird happened that year, too, but I forget what it was. It couldn’t have been important.

Correct. Post-season refers to the World Series only before 1969. As many people are no longer aware, the Cubs went to the World Series–but lost it–in 1910, 1918, 1929, 1932, 1935, 1938, and 1945.

The Cubs’ failure to even reach the World Series since 1945 is actually more remarkable than their failure to win it since 1908. The natural odds of the pennant-less streak are 0.18%, as compared to 0.44% for the championship.

When I was growing up (1970’s), this aspect of Cubbie failure was noted more often than the championship drought. As Steve Goodman said (1983), and it’s still true, “the last time the Cubs won the National League pennant was when we dropped the bomb on Japan”.