Chicago Cubs, Jed Hoyer take big “win now” gamble on 2025

The Chicago Cubs have developed a reputation for being conservative and frugal in their talent acquisitions, eschewing big names and big contracts for budget buys and calculated low-risk/high-reward movements.

This year in Cubs history, however, the team has done some very “un-Cubs-y” things.

On the record as being “all in” when it comes to making the playoffs this coming season, the Cubs front office has participated in some big-time gambling when it comes to 2025 and what may remain when it comes to their postseason viability immediately afterward.

The Chicago Cubs Have Made Some Bold Moves

The trade for Houston Astros all-star outfielder Kyle Tucker was a bold move. Acquiring a much-needed impact player cost the team third baseman Isaac Paredes, promising right-handed pitcher Hayden Wesneski, and top prospect Cam Smith.

Most daring in this Tucker deal was the fact that the 28-year-old may turn out to be only a one-year rental. The multi-tool player will become a free agent after the 2025 campaign and could command a multi-year contract in excess of $300 million– a price that, historically, would seem to be too rich for Cubs ownership.

Before Tucker, though, was the decision to sign free agent left-handed pitcher Matthew Boyd to a two-year deal worth $29 million. The oft-injured Boyd, who just returned late last season from Tommy John surgery, was signed based off of just a handful of solid appearances after returning to active duty.

Most recently, the Cubs again knocked on the Astros’ door, this time targeting their former closer and current setup man, Ryan Pressly, for a trade.

The 36-year-old Pressly was a relative steal, only costing the Cubs an A-ball pitching prospect. The Astros even agreed to cover $5.5 million of Pressly’s $14 million contract.

However, like Tucker, Pressly will become a free agent at the end of the 2025 season and will likely be a one-year rental for the team.

Similarly, free agent pickups LHP Caleb Thielbar, ultility man John Berti, and RHP Colin Rea are one-year acquisitions (although the Cubs have a team option on Rea for 2026).

“Win Now”

All of this means, that no matter how well the Cubs do this coming season, they will likely enter into 2026 without their star right fielder, their closer, and a few other assets.

That’s a pretty risky “win now” gambit for a team not necessarily known for taking risks.

Some have speculated that this risk-taking behavior comes as a result of Jed Hoyer’s contract status.

Jed Hoyer’s Job At Stake?

Hoyer, the Cubs’ president of baseball operations, is up for contract renewal at the end of this coming season and it’s not guaranteed that ownership will renew him. Although a big part of the administration that helped build the Cubs’ 2016 World Series team and key in rebuilding their farm system, Hoyer has yet to guide the team to the postseason in four years as the top dog in the Cubs’ front office.

For what it’s worth, Hoyer insists that his moves this year have no relation to his job status next year.

“It’s not going to change any decisions we make,” Hoyer recently told the Chicago Sun-Times. “That’s what people always ask. ‘You’re in the last year, are you guys going to do things differently?’ It’s like, of course not. That’s not my job.

“This is about the fans. This is about Chicago. This is about the Cubs. These things are so much bigger than me. I’m not going to make decisions that impact a city or a fan base based on my self interest.”

Still, the Cubs seem aggressively “all in” this year. The patience for letting their young stars rise and take matters into their own hands has made way for some “win now” pragmatism, with the much-needed rebuild taking place somewhat beneath the surface.

For fans eager to get the Cubs back into the postseason picture, this is good news. Long-term, though, time will tell if the gamble on 2025 was worth what the team had to give up for that roll of the dice.

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