Just a few days after making their first major offseason move by acquiring starting pitcher Edward Cabrera from the Miami Marlins, the Chicago Cubs have stepped forward to break the deadlock atop the free-agent market. As it turned out, the Cabrera trade was merely Chicago’s opening act to the main event: a reported five-year, $175 million deal with third baseman Alex Bregman, an absolute haymaker of a signing that has massive implications on the North Side and promises to cause ripples well beyond the walls of Wrigley Field.
The Cubs reportedly had serious interest in Bregman a year ago during his first trip to free agency, before he agreed to the three-year, $120 million deal with the Boston Red Sox that enabled him to retest the market immediately via opt-out. Sure enough, after a drama-filled campaign that featured the shocking trade of longtime star Rafael Devers to San Francisco — essentially in deference to Bregman as the superior option at third base and the team’s new leader on and off the field — Bregman exercised his opt-out and reentered the market in search of the long-term deal he was unable to secure the winter prior.
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It was no secret that Bregman and his agent, Scott Boras, had no interest in settling for another shorter-term, high-average-annual-value pact. They were seeking the long-term security and firm foundation with one franchise that all premium free agents dream of. As such, it comes as no surprise that the five-year deal with Chicago reportedly contains a full no-trade clause and no opt-outs.
Bregman is now a Cub and will be for a while.
It’s an outcome that is all the more remarkable considering the Cubs’ hesitance to go all-in on Bregman last winter. Sure, there was the imminent arrival of top infield prospect Matt Shaw, who appeared primed to join Dansby Swanson and Nico Hoerner as a fixture in Chicago’s terrific infield. But perhaps more pertinently, the Cubs had lost credibility in recent years as the kind of club that would win any sort of bidding war for a top free agent.
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Last winter, the Cubs made an uncharacteristic, ultra-aggressive maneuver by dealing away valuable future assets to acquire Kyle Tucker entering the final year of his contract, but even so, the franchise’s appetite to spend on the open market appeared to be severely limited. In turn, fans bemoaned that Chicago was unwilling to push its payroll to the heights occupied by the majority of other big-market clubs and that president of baseball operations Jed Hoyer was too often playing it safe with transactions, rather than swinging big.
Such sentiments lingered into this offseason, even after the club returned to the postseason for the first time since 2020 and notched a first-round triumph before bowing out in five games to the rival Brewers in the NLDS. The Cubs’ early activity in free agency consisted strictly of adding low-cost relievers, and there seemed to be virtually no interest in retaining Tucker, prompting concerns about how the offense would perform without his valuable left-handed bat atop the order. Those questions were amplified after the Cubs dealt away one of the young hitters who projected to play a key role in Tucker’s absence — 23-year-old outfielder Owen Caissie — in the Cabrera trade.
But as spring training inched closer, a quartet of premium free-agent hitters — Bregman, Tucker, Bo Bichette and Cody Bellinger — remained unsigned, leaving room for other suitors to emerge late in the process and destroy any preconceived notions about which teams were the favorites to land them. For Chicago, that meant a golden opportunity to dispel the notion that it’s not a major player in free agency and pounce on a much-needed offensive upgrade while other teams sat back and kept their wallets closed. More specifically, it meant a mulligan for the Cubs in their courting of Bregman.
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Coming into this winter, the widespread assumption was that Boston, having fully understood and felt Bregman’s positive impact on and off the field, would make the necessary commitment to retain its third baseman, particularly in the wake of exiling Devers. Other teams ,such as Arizona and Toronto, briefly surfaced as viable alternatives, with the Tigers looming in the background after being involved a year ago.
But as Bregman and Boston remained untethered — and once the Cabrera trade recentered Chicago as a main character this offseason — the Cubs emerged as an intriguing landing spot. While Shaw was Chicago’s primary option at the hot corner as a rookie and showed flashes of promise, it was not nearly the kind of breakthrough season that would preclude a follow-up pursuit of Bregman. All it would take was the kind of contract we’ve so rarely seen the Cubs willing to give out in recent years, save for the seven-year, $177 million with shortstop Dansby Swanson three years ago.
Evidently, Bregman was deemed worthy of a megadeal of that nature, and he’ll now share the left side of the infield with Swanson, another highly accomplished, all-around player renowned for his impact on winning, even beyond what he can do on the diamond. The deal also marks a remarkable pairing of two players whose ties date back more than a decade to when they were selected with the first two picks of the 2015 draft after starring in the SEC for three years.
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With Bregman and Swanson, plus second baseman Nico Hoerner and first baseman Michael Busch both coming off career years, Chicago now has a strong case as the best all-around infield in the sport, especially when factoring in defense. The complicating factor — and an important dynamic to monitor in the coming weeks, if not months — is that Hoerner is slated to hit free agency next winter, whereas the other three infielders are under contract for at least four more seasons.
That leaves Chicago with a few options for how to proceed. The Cubs could keep Hoerner and ride it out with an elite infield until he hits free agency, using Shaw as a utilityman set to replace Hoerner at second base in 2027. They could trade Hoerner now in an effort to improve another part of the roster, such as the outfield. Or — if the Cubs are still in the mood to spend — they could pursue an extension with Hoerner, which would be costly but likely worthwhile, considering how strong the unit could be for the next handful of years. In that scenario, Shaw could be used in a trade sooner rather than later.
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But however the Cubs’ infield shakes out, with Bregman in the fold, it projects to be the foundation on which this roster is built. Moreover, it’ll be fascinating to see how Bregman’s impact is felt on a roster that has a wealth of veteran leadership, headlined by Swanson and the team’s longest-tenured player in Ian Happ. Of course, the intangibles are the bonus feature of Bregman’s résumé as a ballplayer; the hefty contract is the result of his advanced approach at the plate and stellar defense, a balanced package of skills not too dissimilar from what Tucker provided, albeit right-handed and a few years older.
As with any lucrative, long-term, free-agent deal given to a player approaching his mid-30s, it’s natural to look ahead to the sizable sums guaranteed to Bregman down the road, when he might not be the player he is now, and wince a little bit. But for a franchise that should be focused on chasing championships — not fretting about its finances a half-decade from now — making the requisite offer to land a great player and certified winner in Bregman is an undeniable organizational victory for the Cubs. In a matter of days, Chicago has vaulted itself from the group of contenders toiling in winter irrelevance to the inner circle of this offseason’s winners.
And in the grand scheme of free agency, Bregman to Chicago is a refreshing twist in an offseason story that was starting to get stale. The focus now shifts to Tucker, Bichette and Bellinger — and the question of which teams will be willing to step up and make a rejuvenating splash like the Cubs just did.
