All around the Chicago area and across the Midwest, the Cubbies are referred to as underdogs.
As D. J. Gallo explains,
the Chicago Cubs are not underdogs. The Chicago Cubs are a big market team with unlimited resources that has failed, year after year, for the past 106 years. The story of Cubs history is not one of an overlooked band of scrappers always coming up short, it’s a tale of high-profile, highly-paid and over-exposed losers. . .
The Cubs are owned by Tom Ricketts, an investment banking CEO whose family wealth is estimated at a billion dollars, which puts them on Forbes 400 list. He is the son of J Joseph Ricketts, the founder of Ameritrade. Congratulations to him on all his financial success, but the Tom Ricketts story is not an underdog tale.
The franchise’s president of baseball operations is Theo Epstein, who won two World Series titles while running the Red Sox a decade ago, is still only 41 years old and is widely considered to be a baseball management genius. Can a franchise be an underdog if they are run by the top mind in their sport with nearly unlimited resources at his disposal?
The Cubs are paying their manager, Maddon, $5m a year. Jon Lester is one year into a six-year, $155m contract. Kris Bryant, Kyle Schwarber, Addison Russell, Jorge Soler, Javier Baez, Anthony Rizzo and Starlin Castro are, or were at one time, all big-time, highly-touted prospects. The Cubs are underdogs the same way a Victoria’s Secret model is an underdog on Tinder. They’ve just repeatedly messed up what should be a sure thing.