John Henry spending money elsewhere should anger Red Sox fans

When the Boston Red Sox went the entire offseason without a deal with Xander Bogaerts, and wound up losing him to the San Diego Padres, it was clear to fans that, owner John Henry, did not want to spend money in Boston
John Henry (right) stands next to Theo Epstein (left) before a game between the Boston Red Sox and the Cleveland Guardians.
John Henry (right) stands next to Theo Epstein (left) before a game between the Boston Red Sox and the Cleveland Guardians. / Billie Weiss/Boston Red Sox/GettyImages

When the Boston Red Sox lost Xander Bogaerts to free agency on a deal worth less money than a contract extension for Rafael Devers, it was clear to fans that John Henry didn't want to spend money on the Red Sox.

To pour salt on the wound, other members of the Fenway Sports Group seem to have gotten in recent years, and continue to be getting more attention than the Red Sox these days. This is definitely something that infuriate fans in Boston.

John Henry will trade for (and give up) big names in regards to Pittsburgh Penguins

When Henry bought a large share of the Pittsburgh Penguins in 2021, it was originally written off as Henry just buying another team; however, when the 2023 NHL Winter Classic matchup was announced, it was not looked upon very kindly by Boston Bruins' fans as the two teams would be facing off against each other at... You guessed it... Fenway Park.

When walking through the grandstands to watch the game, Henry was booed by fans in attendance after both a poor performance by the Red Sox that season, and for his losing of Bogaerts to the Padres just the week before.

Now, I know, you're thinking, how does this all tie into the Red Sox? Just this past week, Boston was on the precipice of a Wild Card spot, however, they were virtually inactive at the deadline, only mustering up a handful of trades, including one for Luis Urias.

On the flip side, the Penguins just flipped a giant three-team trade where they were able to acquire one of the best defensemen in the NHL in Erik Karlsson. To top it off, he was willing to give up some solid players in order to do so in Mike Hoffman, goaltender prospect Tristan Jarry, and others.

John Henry is willing to spend (and lose) millions in Liverpool, but not in Boston

While Henry has been known to dole out a healthy amount of money to certain players like a Pablo Sandoval, or Hanley Ramirez, he has since corrected his mistakes, and has begun the bargain hunting process since then a la Bill Belichick, or Billy Beane if you will.

Some would even say he has over-corrected for his mistakes as, according to, the Red Sox total active payroll sits $187.6 million, when the luxury tax threshold is $233 million, giving him just over $45 million that he could work with.

In Liverpool, where he owns the local football club, it's been an entirely different story. According to, in 2022-23 Henry spent €137.30 million on Liverpool FC, while only making €80.7 million, giving him a net loss of €56.60. The following year, he spent €112.0, and made €60.70, giving him a loss of €51.3.

Keep in mind, this is just on players, not on stadium improvements, with his highest paid players (Dominik Szoboszlai, and Darwin Nunez) making €70 and €80 million, respectively.

RFK racing is also getting some love, more than five the Red Sox top players

While RFK racing collectively gets a lot of attention from Henry, a lot of it is favored towards co-owner, and driver Brad Keselowski. According to, Keselowski is on the books for $9.4 million every year. Now, that may not seem like a whole lot, but for someone who drives a car around a track around (rounding up here) four times per month, it's a lot of money.

Compare that Chris Buescher, RFK's other driver, who makes $5 million. Both numbers are relatively low, but for a sport that is pretty spread out, and doesn't involve daily events like baseball does, that is a lot of money.

In fact, if you add both of their salaries up, it's nearly five times more than five of some of the Red Sox best players right now. To make matters even worse, they are all making under $1 milion right now.

Needless to say, it's safe to say that if you take a look at the books, you can see that Henry is happy to spend his money elsewhere. Boston though? God forbid, he spend it there.