Hey, for once the Chicago Cubs benefitted from another organization completely botching a free agent pursuit. On Wednesday, the Cubs officially announced the Bregman signing and since the deal first broke things keep looking worse day after day for the Boston Red Sox.
You have to go back to last offseason, when Boston did go all out for Bregman and gave him $40 million guaranteed for one year, in a three-year, $120 million contract that also gave him the opportunity to opt out. By signing Bregman, the Red Sox had to give up their second round pick in the 2025 MLB Draft and lost $500,000 in international free agent bonus pool money after Bregman rejected the qualifying offer from the Houston Astros.
Bregman’s addition created a bit of an awkward situation in Boston’s infield. Heading into the 2023 season, the Red Sox signed Rafael Devers to an 11-year extension worth $331 million, making him their primary franchise player. Devers was resistant to changing positions after the arrival of Bregman, but he did. Then, on June 15, 2025, Boston traded Devers to the San Francisco Giants.
In that deal, the Red Sox received Jordan Hicks, Kyle Harrison and two prospects, James Tibbs III and Jose Bello, as Boston essentially traded Devers as a salary dump. By the way, the Red Sox ended up trading Tibbs a month later in a package to the Los Angeles Dodgers for right-handed pitcher Dustin May. The starter only made six appearances for the Red Sox in the final two months of the regular season, posted a 5.40 ERA in 28.1 innings and missed almost all of September because of an elbow injury. May did not return to Boston this offseason and instead signed a one-year deal with the St. Louis Cardinals.
So, the Red Sox signed Devers to a long extension, a new front office led by Craig Breslow was established. Bregman was signed, you got dinged because he was attached to a qualifying and then Devers was shipped out along with his salary. Bregman then opts out after year one of his deal, but surely the Red Sox would do everything possible in order to re-sign the third baseman, right?
Uhhhh, apparently not.
Earlier this week we recapped how the Cubs did step up to the plate and went out of their comfort zone to eventually agree to a deal with Bregman. However, it certainly appears as though they got a nice assist by the Red Sox, the other team negotiating with the third baseman and the team that really botched this.
A.J. Pierzynski shared a gut-wrenching story for any Red Sox fan who was hoping Bregman would return to Boston. Pierzynski paints a terrible story for the Red Sox front office that essentially boiled down to Boston thinking Bregman and his agent Scott Boras were bluffing when approaching the Red Sox with a better deal.
As we know now, that deal was real and it was from the Cubs.
Previous reports have indicated that not only did the Cubs offer more money, the deferral timeline made the contract more valuable from Chicago compared to Boston and the Cubs actually gave Bregman security, offering him a no-trade clause.
| Cubs Offer | Red Sox Offer |
| 5 years, $175 million | 5 years, $165 million |
| Shorter deferrals | Longer deferrals |
| Full no-trade clause | Refused to give full no-trade clause |
I mean, the deals weren’t that far off. We’re talking about a $10 million difference and when spread out over five years it’s a $2 million difference. The key here was that Boston really wanted to stretch out the timeline to pay out the deferred money and Chicago was flexible when negotiating that aspect of the contract with Bregman. Plus, with young children, Bregman wanted stability and the Cubs had no issues with the full no-trade clause, something the Red Sox refused to offer.
Bregman has been praised not only for his production on the field, but for his value in the clubhouse as well.
Here’s one example of how well respected Bregman was and how pivotal the third baseman was for the Red Sox in 2025, from Section 10 podcast host Jared Carrabis.
It’s clear to me how much the #Cubs value his character and leadership, advocating to push their budget 2 years in a row to acquire him, and changing principles with deferrals/lux tax to do so.
— Northside Soundtrack (@CHC_DataDrive) January 12, 2026
Fascinating excerpt about Bregman’s leadership from the great @Section10Pod here: pic.twitter.com/pXqUbaBmnz
Jed Hoyer’s biggest criticism since taking over for Theo Epstein with the Cubs has been he will only do a deal on his terms. He wants to squeeze out as much value as he thinks he can and if that means not going outside of the team’s comfort zone, then so be it. That’s led to top free agent signing elsewhere and the Cubs missing out.
Well, this time around, it was the Red Sox screwing up, not making an extra effort to sign a beloved player because they wanted the deal on their terms. Hmmm, maybe not apples to apples, but this kind of reminds me of something that has happened before.
A proven leader and winner who did want to return to the Red Sox, but wasn’t offered a contract that met his market and ultimately signed with the Cubs? Just saying…
