Unless the Chicago Cubs do something out of character you can pretty much forget about the possibility of Alex Bregman signing with them this offseason. Maybe it was already a formality that the Cubs wouldn't pay up for Bregman and there are probably several fans who didn't want Bregman in the first place, so this could be viewed as a positive for that sect of the fan base.
According to USA Today's Bob Nightengale the Cubs remain in pursuit of Bregman, but that quest seems destined to end in another failure because the Boston Red Sox are reportedly the favorites to retain Bregman's services and their latest offer might seal the deal.
Red Sox Upping Offer to Bregman
In ESPN's latest free agency update MLB insider Buster Olney reported that not only are the Red Sox willing to pay Bregman big money to get him back, but they could now be in the range of a $170 million contract.
The Boston Red Sox want Bregman and have signaled a willingness to pay him big money — perhaps something in the range of what the Tigers offered him last spring, a six-year, $171.5 million deal.
As you may recall last offseason the Cubs were one of the finalists in the Bregman sweepstakes and they offered the third baseman a four-year contract worth $120 million. Now, Bregman is a year older, coming off a major injury and a lackluster second half of the season.
If the Red Sox are actually willing to commit to either a six-year deal or a contract worth somewhere in the $170 million range, then you can pretty much kiss the chances for the Cubs goodbye. Plus, seeing that the Red Sox have already used deferrals in their previous deal with Bregman, you have to assume they'll do it again to push a deal across the finish line this time around.
Meanwhile, the Cubs have publicly stated that they will not entertain the idea of signing free agents while using deferred money in contracts.
(Previous Update)
It's not a detailed report, but in Jeff Passan's latest rumor dump at ESPN he gave Chicago Cubs fans a cookie, especially those who want Alex Bregman playing his home games at Wrigley Field. Last offseason the Cubs were one of a handful of teams that were finalists for the free agent third baseman, but their offer fell short and Bregman signed with the Boston Red Sox. The 31-year-old is once again a free agent and according to Passan the Cubs will once again pursue him.
Bregman opted out of his contract with the Red Sox earlier this offseason, bypassing the remaining two years of his original three-year, $120 million deal (highly deferred contract) to test free agency for the second consecutive year. The Red Sox would love to re-sign the third baseman, while the Detroit Tigers, another runner-up for his services last offseason, appear to be the most interested in Bregman.
However, Passan also mentioned two other suitors in the Philadelphia Phillies and the Cubs.
Via ESPN.
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.
Not gonna lie, I am surprised that the Cubs are reportedly circling back to Bregman not so much because of what they may or may not think of Matt Shaw, but rather how they've played down the fact of adding a significant bat to their lineup.
Much of the talk coming directly from the Cubs so far this offseason has surrounded the need to address the pitching staff, both in the starting rotation and bullpen, while Jed Hoyer and Carter Hawkins have indicated that offense isn't seen as a top priority.
According to league speculation following the GM Meetings last week the Cubs will be in the market for elite pitching as Dylan Cease, Michael King, Framber Valdez and Tatsuya Imai have all been linked to the team in one way or another. However, there hasn't been much talk about top free agent hitters, including Bregman until Passan's mention on Tuesday.
Bregman had a good 2025 season with Boston as he slashed .273/.360/.462, with 18 home runs and a 125 wRC+ in 114 games. That being said, Bregman did suffer a right quad injury that sidelined him for seven weeks and when he returned the right-handed hitter struggled. Bregman had a slash line of .299/.385/.553, before his injury and .250/.338/.386, afterward.
As for the Cubs, they should be exploring options to upgrade the hot corner because despite a hot second half by Shaw the team ranked bottom five in MLB in offensive production from the position in 2025. Plus, Dansby Swanson is the only position player who has guaranteed money on the books after the 2026 season, so the Cubs can definitely fit another high-priced player in addition to upgrades on the pitching side this offseason.
The Cubs were trying to sign Bregman to a short-term, high AAV contract heading into 2025, but he ultimately worked out that type of deal with the Red Sox. We'll see if Bregman is at all interested in revisiting those talks with the Cubs or if he's more focused on locking in a longterm contract with more guaranteed money.
Alex Bregman turns down Cubs
The Alex Bregman sweepstakes have come to an end with the free agent infielder signing a stunning, three-year contract worth $120 million with the Boston Red Sox. While the $40 million AAV is certainly eye-popping it is important to note that Bregman will have $20 million deferred from each year of his deal, meaning there could be as much as $60 million deferred if the third baseman remains in Boston through 2027.
Bregman, who had substantial offers from three other teams, including the Chicago Cubs, ultimately landed on a short-term deal with the Red Sox for the fourth-highest AAV out of any player in MLB. The three-year contract includes opt-outs after the first two seasons.
Alex Bregman’s three-year, $120 million deal with Boston includes deferred money, sources told ESPN. The $40 million salary is $10 million-plus more per year than others were offering. The Red Sox land the best free agent left on the market. First on the news was @ChandlerRome.
— Jeff Passan (@JeffPassan) February 13, 2025
According to USA Today's Bob Nightengale, the Cubs also offered Bregman $120 million, but it was over four years, coming in at $30 million per season or $10 million less per year than what the former Houston Astros third baseman agreed to with Boston.
Nightengale confirmed Matthew Trueblood's report, when he wrote about the Cubs' proposed four-year offer to Bregman.
The Cubs offered 4 years, $120 million https://t.co/dLwAjNX3gp
— Bob Nightengale (@BNightengale) February 13, 2025
The Detroit Tigers and Astros were also involved with Bregman until the end. Houston seemingly did not come off their six-year, $156 million bid, while the Tigers reportedly offered Bregman more than $170 million over six years.
The Tigers offered Bregman 6 years, $171m.
— Buster Olney (@Buster_ESPN) February 13, 2025
Astros 6/156
His breakdown with the Red Sox: $40m in each of the next three seasons, with some of his salary deferred each year.
Opt-outs in the contract.
