Red Sox's Passive Alex Bregman Approach Allowed Cubs To Swoop In

$175 million is a lot, but...

Sep 25, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) throws out Toronto Blue Jays catcher Tyler Heineman (not pictured) at first base during the third inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

Boston Red Sox fans shouldn't be mad about not offering Alex Bregman $175 million. They should be mad that the Red Sox gave the Chicago Cubs time to do it.

On Saturday night, Bregman reportedly agreed to a five-year, $175 million deal with the Cubs, as first reported by ESPN's Jeff Passan.

Last offseason, the Red Sox's three-year, $120 million bid comfortably beat the Cubs' four-year, $115 million bid. This offseason, it seems the Red Sox got too comfortable. Because as other suitors dropped out of the bidding, and it became clear that the Red Sox and Cubs were the main contenders, Chicago was clearly hard at work.

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Red Sox should never have allowed Bregman's free agency to drag out

A $35 million average annual value for Bregman, entering his age-32 season and coming off an injury-affected year, was more than most projected. But it's entirely possible that the Red Sox allowed the Cubs to talk themselves into that offer.

The fact that reports just surfaced within the past week about the Red Sox making an "aggressive" offer for Bregman was telling. Knowing what we know now, that likely means Boston only just got its offer to five years.

Without knowing the specifics, it's not hard to imagine Boston finally upping that offer, Chicago countering with a bigger five-year deal, and Bregman's camp feeling as if it wasn't worth trying to get the Red Sox to match it.

Because for whatever reason, it seems as though convincing the Red Sox to spend money is like pulling teeth.

All offseason, it's felt like the negativity around the Red Sox was too strong for simply missing out on Pete Alonso and Kyle Schwarber (who was always going back to the Philadelphia Phillies). Now, it's all justified, and finding a pivot is going to be difficult.

Unless stories start coming out about the Red Sox being all-in on acquiring Bo Bichette, it's fair to assume that the Red Sox won't get a true star in free agency. That's a disaster, given the fact that they saved $255 million on Rafael Devers' contract and assured us all they'd spend it.

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