John Henry and the Fans Who Enable Him

“Enablers don’t love. They ruin.” -A.R. Torres

In season 6, episode 23 of Seinfeld, “The Face Painter,” Elaine’s boyfriend David Puddy paints his face while attending a New Jersey Devils game. His reason? “Gotta support the team.” Mind you, this was in the mid-90s when the Devils started their run of three Stanley Cup championships.

I’m not sure if anyone painted their face for Fenway Fest, but I’m sure the reason would have been the same. Gotta support the team.

There was much excitement when John Henry bought the team in 2002. Fans like me had lived through the bleak years of Yawkey ownership. Sure, there were a few World Series appearances, but they all ended in devastating game seven losses. John Henry swept into town with Larry Lucchino in tow and they made one of the greatest decisions in baseball history. They hired Theo Epstein as general manager. Henry let Theo cook, supporting him with trades and free agency signings. He didn’t even flinch when Theo’s moves didn’t pan out, such as the signings of Mike Cameron, Carl Crawford, and (ugh) Matt Clement.

Something changed after the 2018 World Series championship season. Dave Dombrowski was fired in 2019, with the Red Sox having a winning record. Dombrowski had just signed Chris Sale to a $145M extension and Nate Eovaldi to a $68M extension. John Henry and his minion Sam Kennedy were done with high payrolls. They wanted a lackey that would do what they say, cut payroll and build back the farm system so they could have a source of cheap, controllable talent. Enter Chaim Bloom. The rest is history.

On January 11, 2023, the Red Sox signed Rafael Devers to a 10 year, $313M contract. They had previously traded Mookie Betts and let Xander Bogaerts walk because they didn’t want to pay them. Was this finally the signal that John Henry wanted to win again?

Fast forward to June 15, 2025. The Red Sox traded Devers to the Giants, who took on his full salary. The excuse was that he was unwilling to change positions, but let’s call it what it really was, a salary dump. Once again, Henry sent Kennedy to face the media and make his stupid excuses. This continued a pattern of John Henry avoiding the spotlight when there was bad news to report. At the end of the disastrous 2011 season, when the team “mutually parted ways” with Terry Francona, Henry was supposed to be at the press conference but had “car trouble.” I wonder, was it the Bentley or the Rolls?

John Henry and FSG have several businesses, and all are cash cows. He’s raking in the money with the Red Sox. A recent report showed that they earned $574M in 2024 and spent only 42% of that on player payroll, 23^rd in MLB. I think the horrible contracts Chaim Bloom handed out to Trevor Story and Masataka Yoshida have made Henry gun shy. The Red Sox have carried many bad contracts over the years, and Henry has allowed new spending. No more.

So surely there has been a massive fan uprising in response to this new behavior, right? People aren’t going to Fenway or the Red Sox stupid Fenway Fest event, just concluded? Nope. Fenway Fest was sold out. The Red Sox didn’t draw the 3 million per year of their championship years, but they drew 2.7 million in 2025, their highest since 2019.

There is a large portion of the fanbase that is either oblivious to this miserly behavior or just doesn’t care. They will give him their hard-earned money no matter what. I have to give props to @ronniegieger6 on Twitter. I have not seen a better explanation of John Henry’s business strategy:

(Paraphrasing) “He is a brilliant businessman. He can throw out a .500 team and make the same amount of money as if he had a World Series contender. Why spend extra millions when you don’t have to? The problem isn’t him; it’s the fans that continue to support him.”

Ronnie, I couldn’t have said it any better. David Puddy was supporting a championship caliber team. As long as fans put money in John Henry’s pocket, nothing will change. He won’t pay CBT penalties. He won’t sign long term contracts for players over 30. He will wait until the bad money of the Story and Yoshida deals is off the books to authorize new spending.

Maybe a miracle will happen, and the Sox will sign Bo Bichette to a 8 year, $300M contract. Maybe when pigs fly (English), when chicken have teeth (French), or when the sun rises in the West (Hindi). But hey, you’re telling me there’s still a chance!