It is easy to point out and rank the very best seasons in Chicago Cubs history, but ranking the rest is hardly a cut and dry discussion. When the 21st century began, the Cubs had a grand total of three postseason appearances (1984, 1989, 1998) since 1945 and zero series wins in those showings. During that same 54-year span, they had only four years in which they won 90 or more games.
Since 2000, however, the Cubs have been to the playoffs eight times, won seven playoff rounds and had five 90+ win seasons. Oh, and a pennant and World Series win. Certainly did not see that from 1946-1999.
The last 22 years as a whole sure brought a lot more joy to Cubs fans than the previous 54, but there has still been plenty of pain and suffering over the past two decades. Chicago has had seven 90+ loss seasons since the new millennium hit. We have seen some of the very best and very worst of Cubs baseball since 2000.
Just for fun, let’s take a look at each of those squads and put together a rankings list. There will be three tiers: the bottom of the barrel, middle of the pack and the best of the best.