The Cubs made the postseason four straight years from 2015-18, and then a fifth in the abbreviated pandemic season in 2020, making it five playoff years in six. That’s something that had never previously happened in franchise history, although they did win three straight National League pennants from 1906 to 1908 and four in five years, winning again in 1910.
All of that was a strange thing for Cubs fans. As grating as the “lovable losers” moniker is to many long-time fans, the name does encapsulate the feeling most Cubs fans had been suffering up to 1984. There have been books written about the Sisyphean life of Cubs fans before they finally got that boulder to the top of the hill in 2016.