The Chicago Cubs, after working the fringes of the free agent market with apparent exclusive focus on restocking their bullpen, made a huge splash on Saturday night with the reported signing of third baseman Alex Bregman to a five-year, $175 million deal.
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The acquisition of the three-time All-Star came just days after news broke of the Cubs’ trade with the Miami Marlins for pitcher Edward Cabrera. The four day run from Cabrera to Bregman shook the foundation of Cubs fandom after an offseason that had been widely panned for it’s relative lack of urgency and daring.
With this latest move, the Cubs have not only become firm betting favorites to win the NL Central Division, but are also earning some World Series chatter.
With that said, here are some details worth pondering and mentioning in the wake of the big pickup.
Money, money, (deferred) money…
Jul 21, 2025; Philadelphia, Pennsylvania, USA; Boston Red Sox third base Alex Bregman (2) against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Eric Hartline-Imagn Images
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The initial reporting of the deal gave Bregman the highest AAV in Cubs history at $35 million.
Later details, however, have shifted the narrative a bit, revealing a more nuanced deal and one which employs deferred money– something which the owning Ricketts family steadfastly refused to do previously (and something which reportedly cost them a shot at bagging Bregman last offseason).
According to MLB insider Ken Rosenthal, $70 million of the $175 million is in deferred payments, making the deal closer to a per-season hit of $30-$31 million. Exact deferral details have yet to be revealed, though.
The financial arrangement allows for the Cubs payroll to still come in under the luxury tax threshold, thereby avoiding costly financial penalties and potential loss of draft pick consideration. It also allows them some space with which to make in-season acquisitions if necessary.
Bregman’s deal is not the richest in team history. Jason Heyward’s and Dansby Swanson’s contracts registered at 7-years for $177 million and 8-years for $184 million, respectively. It was, however, a welcomed departure from the Cubs’ standard business practice of rejecting deferred-money deals, which have become increasingly popular with players and agents.
Who the Cubs beat out (and how)
Jan 12, 2024; Chicago, IL, USA; Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports
While the Toronto Blue Jays and Arizona Diamondbacks were reportedly in the hunt to land the veteran third baseman, Bregman’s 2025 team, the Boston Red Sox, was considered by many the favorite to seal the deal.
Bregman had quickly become a beloved figure in Boston after coming aboard last offseason on a 3-year, $120 million deal that afforded him the freedom to opt-out after his first year. Celebrated for his on-field presence and clubhouse leadership, it was reported that the Red Sox had made it their top priority to re-sign him.
Their lower 5-year, $160 million offer and a supposed refusal to grant a full no-trade clause, though, would eventually cost them as the Cubs swooped in from the periphery of the hunt with more money and a greater drive to get the deal done.
Chicago’s aggression to sign Bregman this offseason stands in stark contract to their perceived lack of aggression in pursuing him last offseason.
The Cubs’ favored target (and the Dansby Swanson connection)
Sep 7, 2025; Phoenix, Arizona, USA; Boston Red Sox third baseman Alex Bregman against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
In a lot of ways, Bregman is the kind of impact player they had hoped to be getting when they traded for Kyle Tucker last offseason.
Bregman will not only bring top-notch defense and a quality bat to the team, but, unlike Tucker, he is expected to take an active leadership role in the clubhouse. With so many veteran assets set to become free agents at the end of the coming season and a young core about to be left behind, the team needs stable cornerstone leadership guaranteed to be on the roster past 2026.
The deal will make the soon-to-be 32-year-old Bregman a Cub into his age-36 season and there will undoubtedly be some physical regression in his game by then, but the intangibles he provides are expected to offset any on-field downside to the signing. There’s definitely a reason that the Cubs front office has coveted him for the better part of two seasons.
In terms of the immediate future, Bregman will slip somewhere into the middle of Chicago’s lineup as a stable and consistent offensive presence. An elite-level contact hitter with a lifetime .365 OBP and 28 home runs per 162 games, he brings stability to a Cubs offense that was inconsistent throughout the second half of last season.
As an interesting side note, the new Cub will be playing alongside shortstop Dansby Swanson, who was selected with the overall number one pick in the 2015 MLB draft, just ahead of Bregman as the overall no. 2 pick.
All in all, there seem to be nothing but positives with this Cubs-Bregman deal. Starting with spring training, though, the actual work begins.
Chicago Cubs Insider Delivers Blunt Alex Bregman Message
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