Here we are again.
In the ‘Groundhog Day’-esque nightmare that never ends, the ‘urgent’ and ‘engaged’ Boston Red Sox are up a creek without paddle, vessel, and excuse, having lost out on a top – and very sign-able – free-agent target once again.
Alex Bregman, who spoke on more than one occasion during his lone Red Sox season about how much he enjoyed being in Boston and on the team, and made it clear he would welcome a long-term extension, will instead be a Chicago Cub for most, if not the rest of his playing career.
Several similar debacles have plagued the team over the last six years, but this one may just take the cake.
Let’s unpack why.
Facts and figures
The Red Sox offered Bregman five years and somewhere in the $160-165 million range, not far off monetarily from the Cubs’ winning bid of five years and $175 million. Both proposals included deferrals, though Boston’s structure was reportedly decades long.
Chicago pursued Bregman last offseason, too. They landed him the second time around not because the price tag was significantly higher, but because they understood his priorities.
A father of two sons under four, Bregman made it clear he wanted a place his family could call home long-term. In other words, the security of a full no-trade clause.
Boston’s unwillingness to budge on the NTC, more than anything, sunk them. Bregman couldn’t trust that they would hold on to him for the entirety of the five years they offered him; he had a front-row seat last June, when the Red Sox dumped Rafael Devers on the San Francisco Giants, less than two years into his franchise-record 10-year, $313.5 million extension. Which brings us to…
The Devers disaster
What makes Bregman’s decision an even worse failure for the Red Sox is that they haven’t lost one star player.
They’ve lost two.
In that way, though perhaps this is the recency bias talking, it may be worse than the Mookie Betts trade. Maybe. (More on this in a moment.)
It’s impossible to discuss Bregman without Devers. The Red Sox made sure of that when they misled Devers for months about their targets and bids, signed Bregman the first weekend of spring training ’24, and gave him Devers’ job.
Devers was justifiably outraged. In the unwritten rules of this traditional sport, proven veteran players and franchise cornerstones are accorded a certain level of respect. As the club’s longest-tenured player and only remaining World Series champion, he felt it was disrespectful to not have a conversation with him before signing Bregman. Especially, Devers claimed, because he had been promised long-term positional security when then-chief baseball officer Chaim Bloom signed him to the extension.
Manager Alex Cora’s response: “Chaim is in St. Louis.”
From start to finish, the Red Sox deployed a careless, thoughtless, and passive stratagem.
It would have been one thing if Bregman’s deal wasn’t tantamount to a one-year deal with choose-your-own adventure player opt-outs for the second and third seasons.
Or if the Red Sox had played him at second, instead of forcing Devers off third and into the designated hitter role.
Or if they had platooned them, making them co-third-basemen who alternated as the DH.
But the Red Sox destroyed and ended their relationship with their only true power hitter and proven winner for a player who, though an undeniably excellent addition, was here for 117 total games.
When the Red Sox traded Devers in mid-June, they should have immediately poured that money into Bregman, who was on the injured list at the time and vocal about wanting to stay.
“This is a risky strategy for the Red Sox,” I wrote in my Opening Day ‘25 column. “If Bregman opts out at season’s end, what then? Does Devers go back to third, or do the Red Sox again give the position he wants to someone else? … That’s a problem for another day, but it’s a legitimate possibility.”
Now, it’s today’s problem. And the next day’s.
Worst of the worst?
The Betts trade was a mistake of Babe Ruth-ian proportions.
But unlike subsequent superstar-related debacles, the Red Sox could make some flimsy, but legitimate enough, excuses. They were coming off a winning, albeit disappointing season, and four championships in 15 years when they salary-dumped Betts and David Price on the eager Los Angeles Dodgers in February 2020.
The move came after months of Betts’ repeated declarations that he would test free agency after the ‘20 season no matter what the Red Sox offered – though only after they insulted him with a lowball offer right after his tremendous ‘18 season – and as the club entered a farm system rebuild and (self-imposed) financial reset under a new leader in Bloom.
The present-day Red Sox are on the other side of that rebuild, and have no legs on which to stand in this entirely avoidable calamity of losing both Devers and Bregman.
The impact
Each missed opportunity to add or retain a star has saved the Red Sox countless millions.
They have lost infinitely more in every other way.
They were just starting to make inroads with both fans and free agents, after trading Betts, shoving Xander Bogaerts out the door, and so many other messes and mistakes. Goodwill slowly built last offseason as chief baseball officer Craig Breslow acquired ace left-hander Garrett Crochet, signed Bregman, extended Crochet and rookies Kristian Campbell and Roman Anthony, and the team made the postseason for the first time since ’21.
Why would anyone trust the Red Sox now?
They were having a difficult enough time luring free agents before this latest development. Under current ownership, they first transformed themselves into the ultimate, elite destination for players, then turned themselves into a last resort. Imagine telling someone in 2018 that a free agent presented with identical three-year, $40 million offers from the Red Sox and Rays would choose the latter (Zach Eflin). Or that someone would choose a one-year deal with the Dodgers over a multi-year offer from the Red Sox (Teoscar Hernandez).
The irony is that the Red Sox used to undervalue and lose proven homegrown stars and overvalue and overcorrect with free agents. Jon Lester, replaced with Price, for example.
Now, they aren’t even doing the overvaluing and overcorrecting. They have the fifth-most expensive tickets in the majors, and rank 23rd in revenue spent on players.
When a player does want to stay in Boston, like Bregman or Bogaerts, the Red Sox wait too long and are too cautious or unyielding to get a deal done. Refusing to give Bregman a full NTC certainly won’t endear them to other family-focused players.
Breslow’s longest free agent contract was Bregman’s three years that turned into one. Perhaps Bregman’s new five-year pact will age badly, as he turns 32 on March 30, but it doesn’t really matter.
The Cubs, not the Red Sox, will benefit from the many intangibles Bregman brings to the organization and clubhouse. He is a tremendous leader, a proactively supportive and encouraging teammate and mentor to young players. As evidenced by the number of Red Sox players who made public pleas for him to re-sign at Fenway Fest, those qualities will make Bregman an absolute bargain.
What’s next?
More of the same, probably. Why expect anything different?
The Red Sox will pivot to Bo Bichette, the top remaining free agent position player. Outbidding the Philadelphia Phillies and former Boston boss Dave Dombrowski for him is about as likely as David Ortiz coming out of retirement to provide the pop this Red Sox lineup needs.
And when Bichette puts on another team’s cap and signs on their dotted line, the Red Sox will pivot again. And again.
A month from now, Red Sox brass will fly down to spring training and disseminate the usual messages:
They were engaged and operated with urgency this offseason. They are hungry for another crack at the postseason, and confident the players they have will get them there.
Certainly, this time it will work out better for the Red Sox.
Surely, they are on the cusp of making it up to you.
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