Craig Breslow just started a ticking clock on his tenure on Mookie Betts' trade anniversary

Oct 31, 2025; Toronto, Ontario, CAN; Los Angeles Dodgers shortstop Mookie Betts (50) celebrates after defeating the Toronto Blue Jays in the 2025 MLB World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images
Oct 31, 2025; Toronto, Ontario, CAN; Los Angeles Dodgers shortstop Mookie Betts (50) celebrates after defeating the Toronto Blue Jays in the 2025 MLB World Series at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

On February 4, the Boston Red Sox landed one more addition to their 2026 infield in Isiah Kiner-Falefa. The eight-year veteran is a defense-first player who will fill something of a utility or backup role in the Sox's lineup.

Boston is still planning to add to its roster after signing IKF — as it should (subscription required). It's No. 1 offseason priority in the fall was to reunite with Alex Bregman, and after that fell through, ending up with Kiner-Falefa and whichever risky trade candidate it lands is a serious fall from grace.

And it's funny, in a backwards, cosmic sort of way, that Craig Breslow's Kiner-Falefa signing came on the anniversary of the day the Red Sox organization's fall from grace began. On January 4, 2020, the Red Sox, then led by chief baseball officer Chaim Bloom, traded franchise staple and New England darling Mookie Betts to the Los Angeles Dodgers to avoid the embarrassment of refusing to pay him when he reached free agency.

Some Red Sox fans found humor in an inconsequential signing on the anniversary of one of the worst trades in baseball history — sometimes you have to laugh to keep from crying. But Sox fans are also past that point with the current team.

Red Sox signing Isiah Kiner-Falefa on the anniversary of the Mookie Betts trade is a disaster by Craig Breslow

To recap the Red Sox's offseason, they added Sonny Gray and Johan Oviedo in trades and Ranger Suárez in free agency to shore up the rotation. All well and good. Offensively, they allegedly prioritized Bregman, although didn't take their pursuit seriously whatsoever, made a joke of an offer to Pete Alonso, and didn't make an offer to Kyle Schwarber or Eugenio Suárez at all. Willson Contreras is a great addition at first base, but without Bregman, the Sox are essentially running last year's team back.

Now, with days until pitchers and catchers report to spring training, the Red Sox are worse than they were last season offensively, despite desperately needing home run power after the Rafael Devers trade. Breslow essentially replaced Devers with Bregman, then swiftly lost him without putting a comparable player in his place.

Breslow acts at the direction of Red Sox owner John Henry and Fenway Sports Group, which owns all or part of four sports teams and owns stakes in leagues like the PGA and RFK Racing. As reluctant as Henry has been to say it, the Red Sox are no longer FSG's top priority. The amount of money Breslow is allowed to spend, along with the refusal to give athletes security through a no-trade clause so it can free up funds whenever it wants, speak volumes to that end.

Still, Breslow will take the fall for these decisions, as Bloom did before him. Whether that's ethical or not (mind, he's not completely blameless in the Devers fiasco) is a worthwhile debate, but it won't change how Boston's system works. However, there's no denial that the Red Sox's infield has been a disaster since the Devers trade, and adding Kiner-Falefa to the mix doesn't help much — bringing him in on the anniversary of the (modern) trade that broke the Red Sox hurts even more. It could be the start of the end of Breslow's tenure in the front office if he doesn't act quickly to further improve the infield.

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