Chicago Cubs will bring big money, bold mindset to winter pursuits, per insider

The Chicago Cubs are in an odd spot this offseason. As a team that made it to Game Five of the NLDS, they clearly have to be seen as contenders heading into 2026. However, they also have some significant roster holes to fill and will struggle to overcome the almost guaranteed loss of free agent right fielder Kyle Tucker.

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Among the team’s needs is a front-of-rotation starter and an almost complete restocking of the bullpen, as well as a veteran outfield option to serve as insurance for a right field now left to Seiya Suzuki and rookie Owen Caissie.

So far, the Cubs offseason efforts have been somewhat underwhelming, limited to a solid signing of reliever Phil Maton and a minor league deal with utility man (and one-time top prospect) Scott Kingery. They were also reportedly in the running for free agent starting pitcher Dylan Cease, ultimately losing out to the Toronto Blue Jays. But things are most definitely set to pick up as MLB’s winter meetings begin on Monday.

Big money available

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If MLB insider Bruce Levine is to be believed, the Cubs will bring a substantial amount of spending money to the table, as well as a willingness to maybe work out an outside-the-box trade.

In a recent appearance on 670 The Score, Levine talked about Chicago’s expected budget availability:

“The one thing that type of report (Dylan Cease) shows you is that the Cubs are, number one, letting people know they’re going to spend money, and number two, even though they finished second, there is, according to my sources, upwards of $50 to $60 million yet to be spent on this year’s payroll. There’s that flexibility in there for the Cubs right now to probably spend somewhere $45-$55 million, which would even keep them from going over the luxury tax number at about $245M.”

Chicago Cubs are serious about power pitching and deals

Levine would also talk about the Cubs’ mindset headed into this most active part of the offseason, via his Twitter/X account:

“Cubs were one of seven teams bidding on Dylan Cease. The Cub front office is serious about bringing in a power arm. They will be a strong player on Japanese pitcher Tatsuya Imai. Imai must sign by Jan 2nd. Posting fee applies. Trade market open for Cubs as well.”

All of that sounds great, especially when it runs concurrent to The Athletic’s report that the Cubs are showing renewed interest in free agent third baseman Alex Bregman.

Perspective

Having $40-$50 million to spend on player acquisition for the remainder of the offseason (allowing for about $10 million on in-season acquisitions) is a pretty nice position in which to find oneself. There’s also the distinct (and frequently reported on) possibility that they could make a significant trade for a high-end, budget-friendly starting pitcher with years of team control ahead.

With about $115 million possibly coming off the books after the 2026 season (Ian Happ, Seiya Suzuki, Shota Imanaga, Nico Hoerner, Matthew Boyd, Jameson Taillon, Carson Kelly, and Colin Rea will all be free agents), there’s no reason NOT to spend big this offseason in an effort to help lay a solid foundation for beyond next season.

In theory, the Cubs front office could add Bregman and some solid bullpen arms, while swinging a deal for a high-end starting pitcher that might, depending on the trade chip, even bring down the budget a bit. That, of course, is just in theory.

But fans have to be wary of the pattern that has become part of every offseason. The Cubs are reported to be “all in” and serious about spending, but fall out of contention for every targeted acquisition as the price tag becomes too uncomfortable. It happened last winter with Bregman and with a reported willingness to aggressively pursue a trade for pitching. This year, they’ve already lost out on Cease and Ryan Helsley while they watch Tucker leave without putting up much of a fight to keep him.

It would be great to think that the Cubs, so close to contention for a championship, would be willing to truly go “all in” when it comes to putting themselves over the top. Most likely, though, they’ll play things true to form, going “half in” and hoping for the best, happy with a budget surplus and with being just good enough to probably make the playoffs.

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