Chicago Cubs’ Alex Bregman Pursuit Hits Key Roadblock

In this story:
While it has been made clear that the Chicago Cubs are interested in signing star free agent third baseman Alex Bregman, the three-time All-Star and two-time World Series champion's fit on Chicago's roster isn't as obvious.
This is because the Cubs have Matt Shaw at third base. While Shaw wasn't great manning the hot corner for Chicago in 2025 (he posted a season-long .689 OPS), he performed better down the stretch both on offense and defensively.
And because Shaw is a former top prospect, was the Cubs' No. 13 overall pick in the 2023 MLB Draft, and is still just 24 years old, the belief is that the franchise wants to give him another shot to succeed in 2026.
But the Cubs could solve this by moving Shaw to second base and then trading Nico Hoerner, which could open up room for Jed Hoyer and the rest of Chicago's front office to sign Bregman. Hoerner will become a free agent after next season, after all, and is already garnering trade interest from other clubs.

Insider explains why Cubs face tough path in Alex Bregman chase
However, just because the Cubs could trade Hoerner doesn't mean they'd like to. New York Post insider Jon Heyman conveyed this during a December live stream when assessing Bregaman's potential landing spots.
"Bregman, it's the same teams: Boston, Cubs, Arizona, and Toronto. So we've got four teams. [Bregman is] certainly just waiting for that right deal, and we assume the right deal is probably at least five years if he can do it. Last year, he went for a shorter-term deal, opted out," Heyman said.
MORE: Tatsuya Imai’s Candid Free Agency Admission Creates Ideal Cubs Opportunity
"Cubs, it feels like the Cubs need to make a trade to [get Bregman], so a little bit less likely for them," Heyman continued. He then mentioned that the Arizona Diamondbacks might need to trade star infielder Ketel Marte to sign Bregman, then added, "I could see them moving Marte more than I can see the Cubs moving [Nico] Hoerner."
At another point in the live stream, Heyman said, "Obviously, Scott Boras represents both [Cody Bellinger and Bregman]. He's got a deadline with Imai and Okamoto coming up within the next week. I'm not sure that would affect the timing, certainly would do a Bellinger or a Bregman deal if the right deal came along."
Nico Hoerner is one of the leaders in Chicago's clubhouse and appears to be in his prime. Yet, if trading him will help the Cubs sign Bregman, some would surely say that dealing him away is worthwhile.
The Latest Chicago Cubs News
MLB Insiders Give High Praise To Top Cubs Pitching Prospect
Why Young Cubs Slugging Option Is Prepared For Breakout Season In 2026
Four Cubs Poised To Make Up Lost Kyle Tucker Production In 2026
Cubs’ Bullpen Outlook Could Depend On 1 Bounce-Back Candidate

Grant Young is a Staff Writer for On SI’s Chicago Cubs, New York Mets, Boxing, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.