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.

Still plenty of Chicago Cubs pride for several decades after 1907 and 1908

The period from 1910-1945 marks a span of 35 years during which the Cubs won all of their post-1908 and pre-2016 pennants. After missing out on the World Series in 1909, despite winning 104 games, they won their fourth pennant in five years. They would win a total of seven pennants through 1945. That was third-most in the National League behind the Giants and Cardinals during that time.

In addition to those pennants, the Cubs won 90+ games 10 times, had 25 winning seasons (above .500) and only finished dead last once (1925) over that stretch. The 1930s were particularly special as they won three pennants and never finished below .500 in a season.

Even after the championship core of Joe Tinker, Johnny Evers and Frank Chance moved on, the Cubs still boasted some excellent players of these decades. Among these players included future Hall of Famers Hack Wilson, Rogers Hornsby, Pete Alexander, Gabby Hartnett and Billy Herman. Future legendary Yankees manager Joe McCarthy began his MLB managerial tenure with the Cubs and won the 1929 pennant in Chicago.

Despite losing seven World Series over this span, the team saw so much success. Wilson’s 1930 season where he hit 56 home runs and drove in a record 191 runs was one for the ages. The clutch “Homer in the Gloamin'” by Hartnett in 1938 was one of the decade’s great regular season home runs. Charlie Grimm was the manager of three of the seven pennants, and he would finish with the second-most wins by a manager in Cubs history.

It was the next 50-some years when the Cubs showed the world what sports futility was all about.

Chicago Cubs: Early in the 21st century, respectability finally returned

The 2003 Cubs behind Mark Prior and Kerry Wood did something the team had not done in 95 years, winning a postseason series. Despite the heartbreaking ending of that season in the NLCS, it was the first of four postseason appearances for the Cubs over the next 12 years. In less than 15 years the Cubs made the postseason more times than they did in the previous 56. By the end of 2015, they won two playoff series and a wild card round, to boot.

2007 and 2008 marked the first time since 1907 and 1908 that the Cubs made the postseason in back-to-back years. They also won 97 games twice – in 2008 and 2015. They had not won at least 97 games in a season since 1945. During those those 13 years, they had six winning seasons.

That is not to say there were not some rough seasons in this era. The 2006 Cubs lost 96 games and the Jim Hendry era fell apart in 2010-2011. When Theo Epstein came in to rebuild the franchise into a contender, the Cubs lost 101 games in 2012, followed by 96 losses in 2013. At least the rebuild years were part of a plan, while most of the losing done from 1946-2002 was just the teams not being good.

To sum this all up:

From 1909-2015, the Chicago Cubs have amassed seven pennants, 14 total postseason appearances and 46 winning seasons. Only 21 percent of those postseason appearances and 30 percent of those winning seasons took place during the span of 1946-2002. That span of a little over half a century was what truly defined the franchise’s futility.

Everything ended in 2016. The 1945 World Series was when the supposed “curse” started, and it lasted 71 years. It is easy to forget, it was really long ago to be fair, that the Cubs of the 1910s, 20s and 30s saw a lot of success and were still a highly regarded franchise despite that being the start of the drought.