How truly futile were the Chicago Cubs during those 108 years?

Chicago Cubs: The long history of losing for the team has been oversimplified.

For 108 years, the Chicago Cubs did not raise a championship banner, giving them the longest championship drought in American sports by a pretty wide margin. It is pretty hard to go over a century and not win a single title, especially considering how many great players the Cubs have had over the years. “Mr. Cub” Ernie Banks, Ron Santo, Billy Williams and Fergie Jenkins never saw a single postseason game on the North Side.

It was easy to say they were horrible for 108 years as, at the end of the day, the ultimate goal is winning a World Series. As Billy Beane (Brad Pitt) says in the film Moneyball, “If you lose the last game of the season, nobody gives a [bleep].”

Just how futile was that era of championship-less baseball for the Cubs? Is it accurate to say they were just awful for 108 years? Honestly, the story is a bit more complicated than that. In fact, the Cubs really were not known for being futile until around half a century after their last World Series win in 1908. Despite not winning a title, there was an era post-1908 and pre-2015 when the Cubs were still considered one of the better franchises in the National League.

To explore the history of the World Series drought, we have to break it up into several eras to really get a grasp of when the franchise reached its lowest points. Not talking about postseason losses like 1984 or 2003, but when the team was regularly bad year in and year out.