Latest Alex Bregman mystery offer should have Jed Hoyer written all over it

As Alex Bregman continues to languish in free agency, a new offer has reportedly emerged from a mystery team, and it sounds an awful lot like the type of contract structure the Chicago Cubs would present to Bregman's camp. For one, we know the Cubs have shown interest mostly in short-term deals. Still, Bregman reportedly has a new six-year offer with an opt-out after the first season, and when you start to factor in everything we know about the Cubs this winter, it makes sense — even if there are also questions we don't have answers to right now.

An opt-out after the first year falls perfectly in line with the Cubs wanting to free up money for a run at re-signign Kyle Tucker next winter. The risk, of course, is Bregman opting into year two and blowing up the team's flexibility, just like Cody Bellinger did this offseason. That would be risky water to swim in, given the money the Cubs already have committed beyond this year and the fact that the team already likely has to commit to going over the luxury tax in 2026 if they want to retain Tucker long-term. It's not something you want to set yourself up for with an owner who has shown reluctance to spend like other big market teams.

Another factor to consider is that the Cubs have already stated that top prospect Matt Shaw would have ample leash to become the team's everyday third baseman this spring. However, everywhere else you look, the Cubs are getting connected to Bregman at the highest levels of the media. Jim Bowden has gone on record stating that the Cubs are one of the most aggressive pursuers of Bregman, and the New York Post's Jon Heyman has confirmed their reported interest.

So, what gives? Is it Shaw, or are the Cubs legitimately more than just a leverage play?

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Are the Cubs still very much alive in the Alex Bregman sweepstakes?

Blocking Shaw is ill-advised, but the team could circle back to trading Nico Hoerner if they must now that the second baseman has proven that he is healthy. If the team did land Bregman on a short-term basis, the Cubs will likely keep Hoerner this year and give Shaw more time to acclimate. Then you can move Hoerner next year if Bregman opts in, move Shaw to second, or keep Shaw at third if Bregman opts out, given that Hoerner is under control for 2026 as well.

Not only does Chicago want to stay under the luxury tax, but they want to keep roughly $8-10 million available for trade deadline acquisitions. With the team currently sitting around $207 million in payroll, they couldn't offer Bregman more than $26 million in the first year of his contract. If you want to lure him to Chicago to make it financially worthwhile with the intent of opting out, they will need to get creative, perhaps by deferring money.

The most important thing is that if Houston doesn't include an opt-out, which easily could be added, then Bregman betting on himself with a new team in 2025 on this type of contract structure is brilliant. He could wind up with a better payday next year, or if he has a down season, he can opt in next winter, winding up with around the same contract he would have received anyway.

Bregman's six-year, $156 million deal from the Astros is reportedly still on the table, and you have to assume that any other offer out there right now doesn't beat that by much. Bregman's preference to play in Houston, where he is already established, doesn't make it easy for a team like the Cubs, who, at their most lucrative offer, can only match the Astros' year-one salary from an AAV standpoint. Chicago will need to offer more money to drive Bregman away and perhaps include multiple opt-outs rather than just one after the first year.

Could the Cubs shift focus to a longer deal riddled with player options and assume, at some point, he would opt out? That logic burned them this winter, with Bellinger opting in. Bregman, unlike Bellinger, has routinely been at least a 4.0 WAR player in every year except 2021. It's worth noting that if the Cubs offer Bregman any contract of length, this structure would make sense, especially if they want to give Shaw more time and reevaluate a Hoerner trade next season if Bregman opts in.

Like most Cubs media, I am skeptical that they will land him, primarily due to financial constraints. If I squint my eyes hard enough, I can start to see where it makes sense to give Shaw more time, knowing he won't be blocked forever. A 2025 Cubs lineup with Bregman and Tucker is incredible to think about, and given recent reports of how aggressive the Cubs have been in obtaining him, we shouldn't be completely close-minded just yet.