About 11 months ago, John Henry posted a celebratory picture to Instagram of himself smoking a cigar. It came in the wake of the Red Sox signing Alex Bregman to a 3-year, $120 million contract at the very beginning of spring training. Henry seemed extremely pleased with himself.
He stepped in in the final moments, gave Craig Breslow the green light to make Bregman one of the highest single-season earners in baseball history. It was the move the entire fan base had been hoping for.
The problem was that the contract had opt-outs after each season, so Bregman was free to leave at any point, and that's what he did. After just one season in Boston, the three-time All-Star opted out 40 million richer.
Now, instead of Alex Bregman being a Red Sox for the remainder of his career, he'll be playing the next 5 years in Chicago. And, former franchise superstar Rafael Devers is calling San Francisco home for the next eight years.
Instead of helping, John Henry's involvement has been detrimental to the Red Sox
John Henry smoking a celebratory cigar after what ultimately became one year of Alex Bregman — and the trade of Rafael Devers — says everything about the current state of the Red Sox. https://t.co/EjH1S4U7Jm pic.twitter.com/WXY3RXhm1I
— Joon Lee (@joonlee) January 11, 2026
It seemed odd last offseason when the Red Sox were pursuing a third baseman when they already had one under contract for another nine seasons. But the team promised it would work. Instead, it forced their franchise star off his natural position without warning, alienated him, and created clubhouse problems.
Henry stepped in there again. A last-minute flight from Boston to Kansas City, and a closed-door meeting between him, Devers, and Alex Cora. The details of that meeting have yet to see the light of day, but five weeks later, Devers was taken off the team plane and traded.
Theories have been swirling for a few years that Henry and the Fenway Sports Group don't care about the Red Sox anymore. They've involved themselves in other ventures and other teams, and since 2018, it feels like the Red Sox have been put on the back burner. That was until 2025, when Henry stepped up a little bit, and look where it got the team.
Just three months after Boston's first playoff appearance since 2021, it is in a worse place than it was before the Bregman signing. Self-imposed financial restrictions have made the team operate more like it's in a mid-market, and not the team with the most championships in the century.
What was a celebratory, throw it in your face picture, telling everybody that he is still the man, should now be hung in the Hall of Ls.