Wash, rinse, repeat — a numbingly recurrent pattern in recent years.
The Sox loved Yoshinobu Yamamoto but were nowhere close to the top of the market when it came to pursuing the righthander when he came to MLB from Japan. They engaged with Juan Soto, but their final offer wasn’t near the 15-year, $765 million guarantee by the Mets that it took to land the slugger. They wanted to sign Max Fried last offseason, but their offer fell below that of the Yankees in years and dollars. (To their credit, the Sox rebounded spectacularly from the Fried miss, trading for Garrett Crochet and signing him to be their rotation anchor through 2031.)
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Teams that benefit from incredible revenues are supposed to exercise muscles that mid- and small-market teams don’t possess. Not only can they afford to outspend competitors to acquire players, but they can afford the risk of those contracts souring.
But in recent years, the Sox haven’t flexed an ability to secure top-end free agent talent. Now in his third offseason with the Red Sox, chief baseball officer Craig Breslow has signed just one free agent to a deal of more than two years: Bregman, whom the Sox weren’t going to sign last offseason — the team had all but concluded a trade with the Cardinals for Nolan Arenado — until agent Scott Boras called the Sox and said Bregman would do a short-term, three-year deal with opt-outs after each of the first two years.
From the moment Bregman’s Red Sox contract was proposed and signed, both sides accepted the reality that the likeliest path was that Bregman would opt out after the first year. He did just that.
Still, there was an opportunity to bring him back. Bregman loved Boston, and the Red Sox loved Bregman. The Sox felt confident in their five-year, $165 million offer, but internally wanted to avoid bidding against themselves rather than upping their bid at the start of the year in an effort to close out a deal.
Alex Bregman was a big hit with his Red Sox teammates and the fans of Red Sox Nation.Matthew J. Lee/Globe Staff
It turned out the Red Sox would have been bidding not against themselves but the field. And once again, the field won, this time with the Cubs — maligned in recent years for their own mid-market behavior despite big-market revenues — racing past the Sox with their five-year, $175 million offer that included fewer deferrals than the Sox and a full no-trade clause. (Per industry sources, the agreement with the Cubs was presented to the Red Sox as a fait accompli, without a chance to counter.) And the Sox were left with the hollowed-out feeling that comes from losing a desired player.
Caveat:
The Sox are still a top-10 payroll team as calculated for luxury-tax purposes entering 2026, operating at a similar level to where they finished 2025. And, in the words of one team source, they still have “dry powder” — the money they’d hoped to spend on Bregman — and will continue to pursue upgrades through trades and free agency. It’s certainly possible they end up with a payroll that would rank in the sixth-to-eighth range for 2026.
But that’s not the top-three or top-five status that the Red Sox routinely enjoyed through most of this century — and right now, it’s also not a top-of-the-scale roster. FanGraphs projects the Red Sox’ roster to produce 42.9 WAR in 2026 — a solid ninth in the big leagues, but fourth in the AL East. They live in a division that does not suffer mediocrity, where even “good” is often not good enough.
With the rise of slugger Vladimir Guerrero Jr. and the AL-pennant winning Blue Jays, the AL East has gotten even tougher. Gregory Shamus/Getty
Of course, the standard for the Red Sox is neither mediocrity nor good. They’ve won four titles this century while aiming to forge an elite roster through a healthy mix of homegrown players, trades, and yes, free agents.
The 2004 and 2007 teams benefited from top-of-the-market signee Manny Ramirez (as well as other long-term, expensive additions such as J.D. Drew and Daisuke Matsuzaka), the 2013 team leaned on John Lackey, and the 2018 club received immense contributions from David Price and J.D. Martinez.
Those four titles weren’t won solely because of landmark free agent acquisitions. (Indeed, the 2013 Red Sox coalesced one year after the team dumped long-term deals for Carl Crawford and Adrián González.)
And it’s possible to produce an excellent team without premier free agents. The 2017 and 2022 Astros (trash can-banging asterisk noted for 2017) and Atlanta in 2021 serve as examples of teams that didn’t play heavily in free agency but still won championships.
But the Red Sox know their best teams in the past employed top-end free agency as a tool, and their chances of forging an elite club moving forward will require them to do the same.
“The best organizations use all weapons at their disposal to put a championship team out there,” Red Sox CEO and president Sam Kennedy said at Fenway Fest on Saturday, hours before Bregman’s agreement with the Cubs. “It’s really important that we focus on using all of the different ways to get players on this roster and not to discard or dismiss any of them.”
In recent years, even if the Red Sox haven’t technically ignored the free agent route, their inability to consummate a major deal has had the same effect: The Sox have failed to employ one of the few avenues that exist to add (or retain) elite talent, leading to the same question echoing around the industry: When will the Red Sox start behaving like a heavyweight again?
The team, through its actions, is the only one capable of providing an answer.
Alex Bregman signing with the Cubs leaves a hole in the Red Sox infield.
Alex Speier can be reached at [email protected]. Follow him @alexspeier.
