Just days after making the first major move of the offseason by acquiring starting pitcher Edward Cabrera from the Miami Marlins, the Chicago Cubs have stepped up to break the deadlock in free agency. As it turns out, Cabrera’s trade was just the opening act for Chicago’s main event: a reported five-year, $175 million deal for third baseman Alex Bregman , an absolutely massive signing that has a huge impact on the North End and promises to cause ripple effects beyond Wrigley Field.
The Cubs reportedly had strong interest in Bregman during his first free-agent trip a year ago before he agreed to a three-year, $120 million contract with the Boston Red Sox that allowed him to immediately retest the market by opting out. Sure enough, in a campaign filled with drama that saw longtime star Rafael Devers traded to San Francisco — largely out of respect for Bregman as the top option at third base and the team’s new leader on and off the field — Bregman exercised his opt-out rights and re-entered the market in search of the long-term deal he couldn’t get the previous winter.
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It’s no secret that Bregman and his agent, Scott Boras, have no intention of striking out on another short-term, high-per-year-value deal, instead seeking the long-term security and solid foundation of a franchise that all quality free agents dream of. So it’s no surprise that his five-year contract with Chicago reportedly includes a full no-trade clause and no opt-out clause.
Bregman is a Cub and will be for a while.
The results are all the more remarkable considering the Cubs were hesitant to go all-in on Bregman last winter. Of course, top infield prospect Matt Shaw is coming, and he seems ready to join Dansby Swanson and Nico Hoerner as part of Chicago’s outstanding infield. But perhaps more relevant is that the Cubs have lost credibility in recent years as a club capable of winning any sort of top free agent bidding war.
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The Cubs adopted an unusual and extremely aggressive strategy last winter by trading valuable future assets to acquire Kyle Tucker, who was entering the final year of his contract, but even then, the team’s willingness to spend on the open market appeared to be severely limited. Fans, in turn, complained that Chicago was unwilling to push its payroll to the heights occupied by most other big-market clubs and that president of baseball operations Jed Hoyer was too cautious on trades rather than generous.
That sentiment has continued into this offseason, even after the club returned to the playoffs for the first time since 2020 and won in the first round before falling to the rival Brewers in five games in the NLDS. The Cubs’ early activity in free agency has consisted strictly of adding low-cost relievers, and there appears to be little interest in retaining Tucker, raising concerns about how the offense will perform without Tucker’s valuable left-handed bat. Those issues were amplified after the Cubs traded away a young hitter expected to play a key role in Tucker’s absence in the Cabrera trade, 23-year-old outfielder Owen Caissie.
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But as spring training approaches, four quality free-agent hitters — Bregman, Tucker, Bo Bichette and Cody Bellinger — remain unsigned, leaving room for other suitors to emerge later in the process and destroying preconceived notions about which teams are best positioned to acquire them. For Chicago, this represents a prime opportunity to dispel the notion that it’s not a major player in free agency and seize a much-needed offensive upgrade while other teams sit back and tighten their wallets. More specifically, that means the Cubs will need to do some scheduling as they pursue Bregman.
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The consensus is that Boston, fully understanding and feeling the positive impact Bregman has had on and off the field, will make the necessary commitment to retain its third baseman, especially in the wake of Devers’ ouster. Other teams, like Arizona and Toronto, briefly surfaced as viable alternatives, while the Tigers also loomed in the background after getting involved a year ago.
But with Bregman and Boston still untethered — and once the Cabrera trade makes Chicago the centerpiece of the offseason — the Cubs become an interesting landing spot. While Shaw emerged as Chicago’s primary option at hot corner as a rookie and showed promise at times, it wasn’t the kind of breakout season that would prevent a subsequent pursuit of Bregman.
All it takes is a seven-year, $177 million contract signed to shortstop Dansby Swanson three years ago that the Cubs have rarely been willing to give out in recent years. Bregman was clearly deemed worthy of a huge deal of this nature, and he will now share the left side of the infield with Swanson, another accomplished all-around player known for his impact on wins even beyond his impact on the diamond. The deal also marks a remarkable pairing of two players whose connection goes back more than a decade, when they were the top two picks in the 2015 draft after three years in the SEC.
With Bregman and Swanson, plus second baseman Nico Hoerner and first baseman Michael Busch all coming off their careers, Chicago has a solid case for being the best all-around infield in the sport, especially when factoring in defense. The complicating factor — and an important development to monitor in the coming weeks and even months — is that Hoerner is expected to become a free agent next winter, while the other three infielders have at least four more seasons left on their contracts.
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That leaves Chicago with some options on how to proceed. The Cubs could keep Horner and ride it out with an elite infield until he hits free agency, leveraging Shaw as a versatile player poised to take Horner’s second base spot in 2027. They could now trade Horner to improve another part of the lineup, such as an outfielder. Or — if the Cubs are still in the mood to spend money — they could seek to re-sign Hoerner, which would be expensive, but might be worth it given the strength of the division now and in the years to come. In this case, Xiao can be used in trades as early as possible.
But no matter how the Cubs infield changes, with the addition of Bregman, it will be the foundation of this lineup. Additionally, it will be interesting to see what impact Bregman has on a roster rich in veteran leadership, led by Swanson and the team’s longest-tenured player, Ian Happ. Of course, intangibles are extra traits on Bregman’s resume as a player; this massive contract is the result of his advanced rebounding approach and stellar defense, a balanced skill set that’s not too dissimilar to what Tucker offers, despite being right-handed and a few years older than Tucker.
As with any lucrative, long-term, free-agent deal for a player approaching his 30s, it’s natural to look ahead to the large sums guaranteed to Bregman and frown a little when he may no longer be the player he is now. But for a team that should be focused on chasing a championship — without having to worry about its finances five years from now — making the offer necessary to sign a great player and get Bregman certified as a champion is an undeniable organizational win for the Cubs. In a matter of days, Chicago emerged from a field of contenders that had struggled over the winter and had nothing to do with the inner circle of offseason winners.
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In the grand scheme of free agency, Bregman’s move to Chicago is a refreshing twist in an offseason story that was starting to grow stale. The focus now shifts to Tucker, Bichette and Bellinger — and which teams are willing to step up and rejuvenate like the Cubs just did.
