Especially after the 2 last place finishes and a 5th place finish (thanks to the Astros being in the NL). He managed to lose 101 games in one of the years. In the Cubs long rotten history, they had lost 100 + games only 2 other times -- 1962 and 1966. In the three year stretch, from 2012 -2014, the Cubs lost 286 games -- more than any other 3 year period in their history.