The Cubs made the postseason four straight years from 2015-18. That’s something that had never happened before for the franchise, although they did win three straight National League pennants from 1906 to 1908 (and four in five years, with one in 1910).
This is a weird thing for Cubs fans. As grating as the “lovable losers” moniker is to many long-time fans, the name does encapsulate the feeling that the experience of most Cubs fans has been suffering. 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.