Chicago Cubs
The team was very successful in its early years. They won the first National League championship in 1876. They won several pennants in the 1880s and then again in the early 1900s.  After they won their second World Series in 1908, they went into the longest championship drought in the history of North American sports.  They won the World Series in 1907, 1908, and 2016.  They won the pennant, but lost the World Series in 1906, 1910, 1918, 1929, 1932, 1935, 1938, and 1945.