For the First Time Since 2020, the Cubs Aren't Playing With House Money

The last time the Cubs won the division was in 2020, or the shortened, 60-game pandemic season. Before then, it was in 2017, the year they were outclassed by the Los Angeles Dodgers in the NLCS. For all the talk about how great the last Cubs’ competitive window under Theo Epstein was, they only secured three NL Central titles and won six playoff series (including Wild Card games). However, at least one of those series wins ended the longest drought in professional sports history. 

Now, on the brink of Spring Training in 2024, the Chicago Cubs are back in a competitive window. The “not a rebuild” that began in earnest during the 2021 Trade Deadline (though one could argue that it was the Yu Darvish trade in December of 2020 that got the wheels rolling) finally reached its end when the Cubs traded for Jeimer Candelario last season, bucking industry predictions and buying as the calendar flipped to August. The team has acquired significant players to beef up the roster - Shota Imanaga, Michael Busch, and Hector Neris - and rumors still have them pegged as a likely landing spot for at least one of the “Boras Four.” 

The state of the division also resides in the Cubs’ favor. The St. Louis Cardinals, who finished last in the division in 2023, are the projected favorite, with a lineup led by 36-year-old Paul Goldschmidt and 32-year-old Nolan Arenado (as well as a rotation helmed by Sonny Gray, 34). The Milwaukee Brewers added some exciting pieces, including Rhys Hoskins and Gary Sanchez. Still, they’re also down their two longtime aces, Brandon Woodruff (non-tendered due to injury) and Corbin Burnes (traded to Baltimore), and their manager (Craig Counsell, who came to Chicago). The Cincinnati Reds are loaded with young infielders, but their outfield and bullpen leave much to be desired. The Pittsburgh Pirates aren’t awful, but they don’t have many exciting pieces, and calling their rotation average is probably generous.

The Cubs have their flaws, too: first base and third base are currently unsettled (even if Busch steps up and fills one of the corners), the rotation could use one more sure thing, the middle-relief facet of the bullpen is in flux, and the lineup currently has a Cody Bellinger-sized hole. A big-ticket free agent signing or top prospect promotion could and should assuage some of those concerns, but they wouldn’t render the Cubs perfect. Even with a few moves that would make them NL Central favorites, the Cubs would still be looking up at the Atlanta Braves and Dodgers in the pantheon of the National League. 

However, just because they’ll likely be stopped short of the World Series doesn’t mean the North Siders don’t have expectations this year. By all accounts, they should make whatever transactions necessary to enter the regular season as heavy favorites in the central, and they should aggressively promote prospects and buy on the trade market to reinforce an incomplete roster. The Cubs' next competitive window is now, even if Jed Hoyer and the rest of the front office are trying to put it off. Winning in sports is often based on circumstance as much as it is internal and deliberate maneuvering, and the Cubs are being presented with fortuitous division circumstances at this very moment. 

Anything other than a postseason appearance this year would be an abject failure. This isn’t another “retooling” season where winning is a byproduct of luck; winning every game should be the goal. 

The Cubs have benefited from playing with house money in the last few years. In 2024, they’ll be expected to win.