As most baseball fans know, prior to 2016, the answer to this question would have been 1908. However, the Chicago Cubs finally broke through in 2016 to claim that season’s World Series over the Cleveland Guardians (“Indians” at the time) in an exciting seven-game affair. That was the franchise’s third World Series crown; the others came in 1907 and 1908. The Cubs have also claimed 17 National League pennants, the first coming in that competition’s inaugural season of 1876.