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

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.