Alex Bregman is no stranger to having his name float around the Chicago Cubs’ stratosphere.
Fans may remember that, ahead of the 2025 season, the Cubs were one of the teams actively pursuing Bregman when he hit free agency after the 2024 campaign. Chicago’s front office reportedly offered the three-time All-Star third baseman a four-year, $115 million deal — but Bregman and his camp didn’t bite.
Instead, Bregman signed with the Boston Red Sox for a more lucrative three-year, $120 million contract. That deal included an opt-out after 2025, which Bregman took. He’s now a free agent once again, and the Cubs have another chance to land him.
One insider believes Bregman is still a fit in Chicago. MLB Network’s Jon Heyman joined Marquee Sports Network’s Lance Brozdowski on the latest episode of “Cubs Weekly Podcast” to discuss how the Cubs may attack free agency in the offseason.
“Bregman would give them arguably the best defense in the sport,” Heyman said. “They already have three Gold Glove winners; Bregman has won in the past. To me, that makes sense.”
Heyman also included Matt Shaw in the conversation, as Shaw became the Cubs’ everyday third baseman when he returned from a Triple-A stint in May. Signing Bregman, the 2024 AL Gold Glove Award winner at third, would push Shaw out of the hot corner, like it did to Rafael Devers before the Red Sox traded him to the San Francisco Giants in June.
“I think Shaw was pretty decent defensively — better than people thought,” Heyman said of the rookie, who was nominated for a Gold Glove Award at third base this season. “Maybe he’ll be better in his second season — he likely will. But Bregman brings that extra defensive measure.”
Bregman had a productive offensive year despite missing nearly two months with a right quad strain. The 31-year-old slashed .273/.360/.462 (.821 OPS) with 18 home runs and 62 RBI. Those numbers helped him garner his first All-Star selection since 2019, the same year he finished second in AL MVP voting with the Houston Astros.
The Cubs, of course, are the incumbent team of top free agent and another former Astro in Kyle Tucker, who will likely cost more money than the team has ever handed to a free agent. And since it’s looking more and more likely that Tucker will sign elsewhere, Bregman or former longtime Cub Kyle Schwarber represent much more intriguing options for the Cubs.
“Both Bregman and Schwarber would be half the price of Tucker — and probably would get a bigger, positive reaction from Cubs fans,” Heyman said. “I would say Schwarber and Bregman are probably more likely (to sign) than Tucker for the Cubs.”
Heyman wasn’t sure whether the Cubs will necessarily be a favorite to sign a free agent bat this winter, but he was firm in the fact that they will put pen to paper with at least one of those names hitting free agency.
“Do you need to be the favorite for one? You just need to sign one,” Heyman said. “I think they’re a really good team that needs a little extra offensive push. You need one. And I do think they are the favorite to sign one.”