Chicago Cubs need to change their standard off-season approach this winter

Understanding the Chicago Cubs' outlook for 2024 and what it means for Jed Hoyer in terms of getting uncomfortable with bigger contracts.

San Diego Padres v Chicago White Sox
San Diego Padres v Chicago White Sox / Quinn Harris/GettyImages
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Going back to the winter of 2022, Jed Hoyer has been adamant that he did not want to make free-agent deals that would hurt the team long-term, even if it made the Chicago Cubs immediate World Series contenders. Rightfully, Hoyer has shown his cautious with his spendng by inking players such as Dansby Swanson and Seiya Suzuki. Along with extensions for Nico Hoerner and Ian Happ, Hoyer has identified a core moving forward.

Given the downfall of the Jason Heyward contract, Hoyer opted against signing names at the top of the market last off-season to avoid the Cubs' being financially handcuffed to a deal that is at least 10 years in length. It's safe to say that Hoyer has everything mapped out and understands what's best for a team's short and long-term success.

Unfortunately, none of it matters in today's game. It takes more work. Hoyer's route of doing what's best now and in the future will only get the Cubs so far, as we saw in 2023, by narrowly missing the playoffs. Since players are being offered more money and guaranteed years elsewhere, he must step out of his comfort zone with free-agent contracts to take the next step.

Taking a Juan Soto trade, for example. Given Soto is already a generational talent at the age of 25, he is the perfect player you can target via trade and extend to a long-term deal. Feel comfortable that you're getting an elite ballplayer for several years to come. Lock that deal up and throw away the key. Trading for Soto and resigning Bellinger, for example, gives the Cubs one of the most potent offenses in baseball.

There are endless variations of what the front office can do to beef up this team, but one thing is sure: they won't be able to trade for Soto and offer him a five-year extension when he is in line for a monster payday next winter.

It doesn't take much to learn how much money the Cubs make, especially when they are playing meaningful baseball and can give their millions of worldwide fans something to cheer about. The revenue from superstar players will be well worth the contract demands they receive. Ticket sales will be sky-high, which means concession stand sales will be incredible. Merchandise sales will be up. It just all makes sense for Tom Ricketts to invest in this team.

Hoyer may need to loosen the collar when all is said and done, but it's time to shell out the big bucks and get this team back to deep October postseason runs. The kind we were accustomed to from 2015-2020 when playoff baseball on the northside was regular.

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