While Cubs fans might have been getting accustomed to less-than-stellar seasons by the mid-1960s, it’s unlikely any of them were prepared for their second 100-loss season of the new 162-game era.
While there were still standout players in the mix, it was not a time of win-prosperity for the club.
1965 Cubs
Record: 59-103
Standing: 10th in the National League
Managers: Leo Durocher
For the first time in the expansion era, the Cubs found themselves bested by the new franchises, finishing dead last in the National League, a whopping 36 games behind the Los Angeles Dodgers.