Chicago Cubs: Not too great, not too bad either
One could arguably put this in the category of best considering they had three division titles and their first postseason series win since 1908 in 2003. Yet, every time something good happened, it would just go immediately south.
It started off bad, then the promise of Mark Prior, Kerry Wood and Dusty Baker had them on the brink of the 2003 World Series. After the collapse the young stud arms got injured, drama ensued and Baker was gone after 2006. Then Lou Piniella came in and led them to division titles in 2007 and 2008…only to be swept out both times. Other years were either mediocre or terrible. They finished 807-811 in the 2000s. So much hype, but ultimately a disappointment.
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This one can be classified as one of the worst, however, the 1970s can also just be looked at as the most mediocre. They went 785-827-1 which is a .487 win percentage. It led to no postseason berths, and it saw the end of the Bank/Santo/Williams era, but six of those seasons they hovered around .500 and lost 90+ games only once.
Dave Kingman, Jose Carenal and Hall of Famer Bruce Sutter gave the fans some entertainment. Often forgotten is the 1977 season which the Cubs were in first for much of the year until falling towards the end and finishing 81-81.
This is probably the most successful decade not in the top five. The Cubs won the pennant in 1929 only to lose to Connie Mack‘s Athletics in the World Series. They went 807-728-9 in the 20s and had a number of winning seasons, just not good enough to be the top-dogs. It had its share of Hall of Famers suit up for the Cubs including Hack Wilson, Joe McCarthy and Pete Alexander.