The Boston Red Sox arrived at the Winter Meetings soon after making two trades for starting rotation reinforcements and announcing their new focus of adding bats. They left the meetings without adding any hitters, as their two top slugging targets signed with other teams on five-year deals.
The Red Sox attempted excuse their whiff on Alonso by saying his age was a concern — he's 31 years old, and Schwarber is 34, which explains why Boston didn't even make him an offer. Fans have not responded well to the front office's endless whiffs on free agents that have gone back years, and they also haven't taken well to the latest assertion from an unnamed "high profile agent" to Sean McAdam of MassLive and other local Red Sox reporters (subscription required).
“They don’t believe in long-term deals,” the agent said. McAdam later specified that most of the risk associated with long-term deals comes after players turn 30.
Gabrielle Starr of The Boston Herald also reported an external opinion of the Red Sox's shortcomings: "The outside perception is that the Red Sox are OK with finishing these free agency races as also-rans. One free agent told the Herald it was “beyond confusing” to see how they operate" (subscription required).
These comments do not bode well for a potential reunion with Alex Bregman, who hoped for a five-to-six year deal starting in his age-31 season. The Red Sox didn't give him that last year, and it's incredibly difficult to believe they'll meet his price now that he's a year older. Losing out on Bregman due to yet another pathetic offer despite the team's billions will be unacceptable, and should be the final straw for fans who regularly spend money on the team, whether it be merch or tickets to games.
Anonymous agent and player roast Red Sox for embarrassingly low offers to free agents
Fans have seen Boston's aversion to long-term deals materialize since it won the 2018 World Series. Every offseason since then has been full of hot air and lies from the front office about its intentions to make the big signing to be fully invested in winning, only to make a pitiful offer to be purposely beaten out by another club.
Boston has gone to extreme lengths to avoid keeping long-term contracts on its payroll. It endured criticism from fans and media after trading Mookie Betts and allowing Xander Bogaerts to walk, and those criticisms continue to this day — the Betts trade is possibly, if not certainly, one of the worst in baseball history. The Red Sox also traded Rafael Devers away just a year and a half into his 10-year deal, the largest in the organization's history, due to a miscommunication that began with the front office.
Some defenders of John Henry's ridiculous cheap behavior will argue that the Red Sox extended Garrett Crochet and Roman Anthony in 2025, and that Ceddanne Rafaela and Brayan Bello's long-term deals invalidate this external criticism. Bello and Rafaela's deals are insanely cheap, at six years for $55 million and eight years for $50 million, respectively. Anthony's eight-year, $130 million contract essentially bought out his arbitration years and added two on the end. Boston didn't have to compete with another team to reach that deal, and if it did, it would've been blown out of the water.
The Red Sox know they can't shortchange free agents because they've seen the same strategy fail them time and time again. Every time it happens, it looks more and more like that was their plan all along — feign competitiveness just to lose out and pinch Henry's billions and billions of pennies, despite promises to explore all angles to improve the team.
And that's why the Red Sox haven't won anything of consequence and have only twice made the playoffs since 2018. The league's top players will always refuse to sign with a team that won't pay them what the market dictates they're worth, and Boston will remain uncompetitive as long as it maintains this loser approach.
If the Red Sox want to be taken seriously, they need to get real and meet the market for the players they need. They haven't been serious for years, and its tainting players', agents' and other teams' opinions of them. Their fans have had it, too.