In 1969, the Cubs were 24 years from their most recent league pennant and that honestly didn’t feel too long. Of the “Original 16” teams, two others (Indians, 1948 and Phillies, 1950) had similar droughts and the Athletics franchise hadn’t appeared in one since 1931, two cities ago.
So while Cubs fans had gone through 20 years of bad baseball, finishing over .500 just once between 1947 and 1966, it wasn’t the century-long drought that took on a life of its own in 1969. With Leo Durocher taking over as manager in 1966 and the team suddenly in contention the following year, it seemed at the time just part of the cycle of baseball.