Feb 18, 2019; Lee County, FL, USA; A general view of a Boston Red Sox helmet as Boston Red Sox center fielder Jackie Bradley Jr. (19) walks on the field during a spring training workout at Jet Blue Park at Fenway South. Mandatory Credit: Jasen Vinlove-Imagn Images Jasen Vinlove-Imagn Images

Insider Predicts Red Sox To Keep 3-Time All-Star Thanks To Roman Anthony Extension

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Sep 5, 2025 12:00 PM ET

Roman Anthony may be gone for the rest of the regular season, but he's staying with the Boston Red Sox for the long haul.

Anthony's 71-game major league debut was a massive success this season, and the Red Sox did well to lock him up on an eight-year, $130 million extension with escalators and a 2034 club option. But there's much more business for chief baseball officer Craig Breslow to attend to this offseason.

First and foremost, the Red Sox have to find a way to keep three-time All-Star third baseman Alex Bregman. Boston traded Rafael Devers in June, who was disgruntled in large part due to Bregman usurping his third base position, so losing the latter after only a year would be a PR nightmare.

Red Sox predicted to keep Bregman

On Thursday, FanSided insider Robert Murray wrote about the Red Sox's free agency dilemma with Bregman, ultimately predictingthat the 31-year-old would stay in Boston thanks in large part to the vision for the future the Red Sox can present, highlighted by the Anthony extension.

"The competition for his services will only drive up the bidding in the offseason, but the Red Sox are equipped to meet those demands," wrote Murray. "My guess is that Bregman ultimately stays in Boston on a new contract, but considering that talks likely haven’t even happened yet means it’s anyone’s guess where he is in 2026.

"... But surely the Red Sox’s activity, especially the Anthony extension, were about two things in mind. 1) ensuring the foundation of the organization is set and 2) with keeping Bregman in mind."

Bregman loves batting second behind Anthony in the lineup, and when he called the youngster's injury a "gut punch" on Tuesday night, it was clear he already views the 21-year-old as one of the very best hitters in the entire sport.

For a veteran who wants nothing more than championship rings, Anthony is the best possible young player for Bregman to hitch his wagon to. But the money still matters, and after only being willing to give Bregman a short-term contract last winter, the Red Sox will have to make a longer commitment this time around.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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