For most of John Henry's two decades running the Red Sox, you could question individual decisions, but never his motives.
Unlike publicity-hungry Patriots counterpart Robert Kraft, Henry prefers the background. Rarely has the camera found his owner's box, and his next press conference will be his first since early 2020.
Henry's reticence is annoying in good times, but generally tolerable when the team is doing everything it can to compete. He may not have much to say, but money talks, and for years Red Sox fans knew he'd extend himself to field a winner.
Those days feel disorienting and distant. Today, Henry is the owner fans jeer while rooting against his newest priority.
The NHL didn't do Henry any favors by sending his Pittsburgh Penguins to Fenway Park for a Winter Classic matchup with the Bruins on Monday. Pittsburgh's presence merely reminded Red Sox fans of Henry's divided loyalties. While he buys hockey teams, tries to score an NBA franchise alongside LeBron James, and figures out exactly what to do with his foundering Liverpool soccer club, the Red Sox languish.
They're in the midst of one of their most disappointing offseasons ever, playing perpetual bridesmaids in free agency and losing more talent than they've added. The days of Theo Epstein breaking furniture and Larry Lucchino breaking heads over the likes of Jose Contreras and Mark Teixeira choosing pinstripes are over.
Boston Red Sox
Now, the Red Sox can't even win bidding wars for relatively modest talents like aging DH Jose Abreu or nondescript right-hander Zach Eflin. They never made fan-favorite shortstop Xander Bogaerts a competitive offer, they somehow lost Nathan Eovaldi to the Rangers despite clearly wanting him, and they face a reckoning with third baseman Rafael Devers, whom no one will blame if he races to free agency in a fashion that's both fast and furious.
The Red Sox haven't felt this disengaged since Scott Cooper represented them at consecutive All-Star Games in the early 1990s. Not only do they look bad on paper, they're almost completely devoid of star power. The through line from Nomar Garciaparra and Pedro Martinez, to David Ortiz and Dustin Pedroia, to Bogaerts and Devers was supposed to remain unbroken. Instead, it hangs by a thread. God forbid they reach the point of no return with Devers or there'll be no one to cheer except maybe manager Alex Cora.
And so it is that Henry, in a rare public appearance, found himself heckled and booed in his own ballpark on Monday. Two fans recorded themselves imploring him to sign Devers -- or anyone -- as he parked his car. Another had his pro-Devers sign confiscated. Boos greeted him in the concourse. Jake DeBrusk's game-winner in the final two minutes delivered equal parts joy and schadenfreude at the expense of the man hosting the game.
Watching the Bruins disembark wearing vintage 1930s Red Sox uniforms highlighted how far the local nine have fallen. Who would you rather cheer for in those sweet unis -- Nick Pivetta, Alex Verdugo, and Ryan Brasier, or Patrice Bergeron, Brad Marchand, and David Pastrnak?
Whatever anger Red Sox fans feel toward chief baseball officer Chaim Bloom, whose offseason can only be described as ineffectual, it is finally being redirected toward the man writing the checks.
Henry reportedly wants out of Liverpool because he can't compete with oil money in the arms race for talent. He seems to be taking a similar tack in MLB, avoiding showdowns with big spenders like Steve Cohen of the Mets and Peter Seidler of the Padres.
We used to know what Henry wanted, because it was also what we wanted -- to field a winner. Now, who can say? Since hiring Bloom, Henry's Red Sox have generally shown an aversion to paying for top-end talent. They've placed an outsized value on flexibility, be it financial or positional. Rather than build to compete with the Yankees or Astros, they seem content to try their chances at the bottom of the wild card standings vs. the White Sox and Rangers.
As philosophical shifts go, this one is demoralizing. Henry should be prepared to pay for it with empty seats and emptier ratings. His fanbase is growing agitated, and the boos he heard Monday could just be the start.
Red Sox fans may have never really "known" the reclusive Henry, but they thought they knew what he was about. Sometimes he regretted big swings like Pablo Sandoval and Carl Crawford. Other times he struck gold with Keith Foulke or J.D. Martinez. But no matter our grievance of the day, in the big picture, we trusted Henry to run the team.
Now? It's starting to feel like maybe somebody else should have a turn.