Back in early 2016, I took a look at the Cubs’ roster and concluded that they had a two-phase window of contention. The first of those (2016-17) was based on a rotation that boasted two years each of veteran starters Jake Arrieta and John Lackey, plus John Lester in his prime. The second phase (2018-21) was based on a young position-player group that boasted potential superstars at every spot on the infield.
I felt the first phase represented Cubs’ best chance, and indeed that proved the case, but I thought they would stay a playoff team though 2021.