Chicago Cubs: 10 greatest all-time teams in franchise history

The Chicago Cubs have existed in one form or another for well over a century – and during that time, they’ve fielded quite a few remarkable teams. Though World Series winners just three times in franchise history, the North Siders have had their share of exceptional runs, especially as of late.

As we all are well aware, they have had quite a few “almosts” over the years, as well. In this list, we will take a glance back in time as we compile the most successful teams in the franchise’s illustrious history, dating all the way back to the start of the team itself in 1870 as the Chicago White Stockings.

Though there are many significant moments and seasons in Cubs history, we have gone with mainly the ones who made the deepest runs – regardless of record. We will discuss certain Cubs legends that made incredible contributions on the field and some that eventually gained baseball immortality in Cooperstown.

From the days of World Series ties instead of declaring a winner, or 150 years ago in the 1870s with only eight teams in professional baseball to most recently winning it all five years ago, you might find that just because it took 108 years to win it all again, that doesn’t mean Chicago was simply irrelevant the rest of the time.

Even though most Cubs fans have experienced more losing than winning over the years, the franchise is rich with groups that made deep postseason runs going all the way back to the early 1900s. We all know it took the Cubs more than a century to break the curse, which at the time stood as the longest drought without a title win in the history of American sports, but the seasons of heartbreak in between were still nothing short of amazing from a historical standpoint.