A 92-70 record was good enough for the Chicago Cubs to clinch a spot in the NL playoff bracket. After a three-game Wild Card series win over the San Diego Padres, the Cubs squared off against their division rivals, the Milwaukee Brewers, in an NL Division Series (NLDS) matchup. Chicago lost in five games to Milwaukee, starting their offseason earlier than the team would have hoped. With superstar outfielder Kyle Tucker set to lead a host of Cubbies free agents into the open market, MLB insider Jon Heyman implored the team to sign a big-name free agent this winter via X, formerly Twitter.

“Time for the Cubs to sign a really big free agent,” stated Heyman on Thursday evening. “They're due.”

It does indeed feel like the Cubs are due. President of baseball operations Jed Hoyer hasn't signed a true big-money name since shortstop Dansby Swanson ahead of the 2023 season. The next offseason, deals for outfielder Cody Bellinger and starting pitcher Shota Imanaga were $133 million combined. Chicago had the 5th largest payroll in baseball last season at $211 million. In order to compete moving forward, Hoyer and the front office need to spend money. Can the Cubbies bring Tucker back to Wrigley Field for the foreseeable future? Or elect to sign another big-ticket free agent instead?

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Cubs need a big splash this offseason to keep up with other contenders

Chicago Cubs right fielder Kyle Tucker (30) reacts after hitting a home run against the Milwaukee Brewers during the seventh inning for game four of the NLDS round for the 2025 MLB playoffs at Wrigley Field.
Mandatory Credit: David Banks-Imagn Images

When the Cubs traded for Tucker last winter, it was well known that the star outfielder could only be in town for one year. Still, Hoyer gave up top prospect Cam Smith, plus starting third baseman Isaac Paredes and young starter Hayden Wesneski, for that one season. Now, after falling short in the playoffs, Hoyer's gamble could fail.

However, if the Cubs can lock Tucker in long-term, then last winter's trade will certainly have been worth it. Tucker would give Chicago a fully formed outfield, with Pete Crow-Armstrong returning to center and veteran Ian Happ in left. Yes, he'd be expensive. However, the Cubbies have been successful in the past when they have retained their stars. Will Tucker be the latest big-money free agent to call the North Side home?