Powered by Roundtable
ESPN Insider Believes Cubs Will Be In Play For Alex Bregman cover image

A star third baseman once pursued by Chicago will return to the free agent market, sparking renewed interest from the Cubs.

There are a ton of question marks surrounding the Chicago Cubs and what the front office plans to do this winter. 

No one truly knows whether the Cubs will be in play for Kyle Tucker, acquire a big-time starting pitcher like Dylan Cease, or go after superstar slugger Kyle Schwarber. These things certainly remain a possibility this early in the offseason. 

However, it appears the Cubs are expected to show some interest in Alex Bregman if he doesn’t return to the Boston Red Sox. ESPN insider Jeff Passan confirmed that in a recent piece earlier this week. 

“The Red Sox love Bregman, who opted out of the final two years and $80 million of his contract, and won’t close the door on a reunion despite having Marcelo Mayer ready to play third. Detroit and Chicago, which pursued him last winter but came up short, will rejoin the fray, with Philadelphia lurking as it juggles multiple potential paths.”

The Cubs were in on Bregman up until the end before the All-Star third baseman signed with the Red Sox on a three-year, $120 million deal. According to reports, Chicago offered him a four-year, $120 million contract with multiple opt-outs included. 

With Bregman once again looking for a new contract in free agency, the Cubs seem to be a potential suitor for him again. 

The 31-year-old hit .273 with 18 home runs, 28 doubles, and 62 RBI across 114 games with the Red Sox last year. Although he missed over 55 games due to a right quad strain, Bregman still finished with a 3.5 WAR and made his third All-Star appearance. 

While signing Bregman would be a nice offensive upgrade over Matt Shaw at third base, it would be surprising to see the Cubs go all in on him this offseason. With the veteran turning 32 years old in a few months, this will likely be the last big contract of his career. 

So, he likely won’t settle for a shorter-term deal. That means the Cubs would have to invest a ton of money in the third baseman. ESPN’s Kiley McDaniel believes Bregman will sign a five-year, $160 million deal this offseason. 

If that is indeed the contract that Bregman gets in free agency, it sadly won’t come from the Cubs. Spotrac already has the North Siders at $188 million toward their 40-man tax payroll for the 2026 season. 

Since we all know the Cubs will not go over the $244 million luxury tax, signing Bregman for $32 million a season doesn’t seem like something the front office would do. Additionally, third base isn’t necessarily a need for this team. 

All that makes it hard to believe the Cubs would outspend teams like the Tigers and Red Sox for Bregman.