BOSTON, MA – SEPTEMBER 13: Alex Bregman #2 of the Boston Red Sox returns to the dugout between innings during the game between the New York Yankees and the Boston Red Sox at Fenway Park on Saturday, September 13, 2025 in Boston, Massachusetts. (Photo by Daniel Shirey/MLB Photos via Getty Images)
MLB Photos via Getty Images
The Chicago Cubs stunned the baseball world by acquiring superstar outfielder Kyle Tucker in a trade last winter, though they came up short on another one of their significant targets.
The team had courted veteran third baseman Alex Bregman before he ultimately chose a contract offer from the Boston Red Sox. But with Bregman opting out of that contract and returning to free agency again this winter, the Cubs could be after him once again.
“After a failed bid to sign Bregman during spring training, the Cubs have shown renewed interest in the All-Star third baseman, according to sources briefed on the club’s offseason planning,” Patrick Mooney and Sahadev Sharma reported for The Athletic. “While certain elements of the roster have changed — and the organization has different momentum from its first playoff appearance since 2020 — the logic that drove the Cubs to pursue Bregman then still applies now.”
Without Bregman in the fold this past season, the team promoted top prospect Matt Shaw to manage the hot corner and he had a solid rookie campaign. But if they are able to add Bregman this winter, Shaw could shift to a new position or return to the minors for some additional development.
And it seems pretty clear that Bregman would be an offensive upgrade over the younger outfielder.
Earning his third-career All-Star season in this past campaign, Bregman slashed .273/.360/.462 with 18 homers. And in an apparent attempt to recruit the veteran to his team, Cubs’ infielder Ian Happ outlined a particularly good fit between Bregman and the team’s existing batting order.
“One thing that’s interesting about Bregman and the Cubs is, just the way that our lineup is constructed and the fact that our young guys are predominantly left-handed, in Pete (Crow-Armstrong), (Michael) Busch, (Moises) Ballesteros, Owen (Caissie),” Happ said during an appearance on Marquee Sports Network. “The fact that those guys are all left-handed, bringing in a right-handed bat helps you a little bit with lineup construction.”
As a key member of the Cubs roster, Happ’s appeal on Bregman is particularly noteworthy. Happ will be entering the final season of his three-year, $61 million contract with the team. He also earned his fourth consecutive Gold Glove Award in this past season while manning the outfield and he might prefer to have a veteran with his own Gold Glove Award take over third base.
“When you have that where you can space out your lefties in between guys that really hit lefties well and make the other manager think twice about it, those things are the advantages to adding a right-handed thumper into the middle of that lineup,” Happ added.