The first few teams that come up in mind when talking about Alex Bregman's free agency are the Boston Red Sox, Houston Astros and the Detroit Tigers. However, the Chicago Cubs could be the dark horses in the waiting to land Bregman.
If that happens, it won't be surprising, given the Cubs' affinity with Astros players this offseason. They traded Kyle Tucker from the Astros, and, last week, they got their closer from Houston, Ryan Pressly.
During his podcast on Wednesday, MLB insider Jon Heyman shared his take on the possibility of Bregman signing with the Cubs.
"The Cubs are an interesting team; they’re a fun team. We just saw his great friend Ryan Pressly leave the Astros to go to the Cubs. That may be an extra allure for Bregman. I know that he and Pressly were close—maybe the Cubs could come in there," the insider said (14:23 onwards).
Jon Heyman: A competitive offer could be key to landing Alex Bregman
One reason why Alex Bregman is still a free agent with less than a month away from Spring Training is because he didn't take the Astros up on their reported six-year, $156 million, offer in November.
Jon Heyman believes that among the Red Sox, Tigers, Astros and the Cubs, whoever extends the length of the contract could end up landing the third baseman.
"One of these other teams is going to have to step up, and if they do—if they step up and go to that sixth or seventh year—the Cubs or Red Sox might be able to nab him because we all know where the Astros are, and that wasn't good enough," Heyman said.
Despite the Cubs’ growing appeal, Houston remains a serious contender for Alex Bregman.
“If I had to pick one team today and just guess, I might guess the Astros,” the insider added.
Whether Bregman chooses to stay in Houston or head to Chicago, Boston or Detroit will largely depend on which team offers the best deal — both financially and in terms of team environment.