Insider's shot at Red Sox over Alex Bregman makes Cubs' financial gap look way bigger

The Cubs doing this is what fans have been begging for.
Jan 14, 2026; Chicago, Illinois, USA; Chicago Cubs third baseman Alex Bregman attends with his family an NBA game between the Chicago Bulls and Utah Jazz at United Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images
Jan 14, 2026; Chicago, Illinois, USA; Chicago Cubs third baseman Alex Bregman attends with his family an NBA game between the Chicago Bulls and Utah Jazz at United Center. Mandatory Credit: Kamil Krzaczynski-Imagn Images | Kamil Krzaczynski-Imagn Images

Alex Bregman continued his tour of Chicago on Wednesday as he was in attendance for the Chicago Bulls' game against the Utah Jazz. The Cubs announced the signing of Bregman on Wednesday, and the All-Star third baseman will have his introductory press conference on Thursday morning. Among the questions that will be asked is how negotiations with the Boston Red Sox fell apart.

Similar to how Bregman spurned the Cubs last offseason when they submitted a four-year proposal that didn't include derrals, wasn't for the most years, didn't carry the highest AAV or the most overall money, the Red Sox discovered this offseason that their offer to their incumbent third baseman simply wasn't the best on the table.

Bregman is now with the Cubs, and the Red Sox pivoted quickly. Boston signed free-agent starting pitcher Ranger Suarez to a five-year deal worth $130 million. While there was speculation that the Red Sox would respond to their whiff on Bregman by focusing on improving their pitching staff, it was notable that they paid Suarez beyond what most projections had for him at the start of the offseason.

Honestly, it's a move that is almost on brand for the Cubs. Say one thing is your need, but then do everything in your power to avoid addressing it. Last offseason, after the Cubs traded for Kyle Tucker and salary-dumped Cody Bellinger to the New York Yankees, the team sat on the money they saved. It was a disappointing end to an offseason that was highlighted by the team striking out on their chase for Bregman.

A year later, the Cubs have reversed course, taken advantage of Boston's lull, and reeled in Bregman to one of the largest contracts in team history.

Considering the signing came on the heels of Bregman choosing the Cubs, ESPN's Buster Olney was quick to point out just how much Boston slighted someone who was their stated priority after the season concluded.

Insider piles on Red Sox over Alex Bregman and makes Cubs' deal look even better.

It's why Bregman's arrival to the Cubs feels special. Under Jed Hoyer and Co., Cubs fans have grown used to the idea of "we tried," only to find out the team's offer barely held a candle to the deal that was signed. Instead, it was Chicago who took advantage of another team botching their negotiations.

The Cubs are likely done with their heavy lifting this offseason, something that is a far more comfortable thing to say after the moves they've made in the week leading up to the Cubs Convention.

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