John Henry You Have One Job
It’s time to correct the mistakes that have been made over the last eight years
On February 3, 2019, Boston was at the pinnacle of the American sports world. The Patriots had just won their sixth Super Bowl and a few months earlier the Red Sox won their fourth World Series since 2004. Robert Kraft and John Henry were the greatest owners in Boston sports history, and it wasn’t even close. Sure, Wyc Grousbeck and his ownership group would go on to win a second NBA title in 2024, but then they promptly sold the team. Nobody alive today probably remembers Walter Brown, who founded the Celtics, but his teams were the first dynasty of the NBA.
All of these owners did one thing right. They hired the right people to run the sports side of the business. That is truly the one job of an owner of a sports franchise. Unless you’re Al Davis or Jerry Jones, you’re not going to be involved in the day-to-day operations of the team. Most franchise owners have become billionaires in the business world. You don’t get to that point by hiring ineffective leaders. However, once these same people own sports franchises, they make all sorts of dumb decisions. Making money with a sports franchise and having success on the field are two different things. Most owners excel at the former and fail at the latter. Why is that?
Robert Kraft had been a Patriots fan since their days in the American Football League and like many New Englanders, didn’t have a football team to root for until 1960. Through a series of moves, Kraft bought the land, stadium, and eventually the team in 1994. He inherited Bill Parcells as coach and went to a Super Bowl in 1996, which they lost. Kraft’s first coaching hire was Pete Carroll, but his master stroke was luring Bill Belichick away from the New York Jets. He gave Belichick total control of the team, including scouting, drafting, and player personnel. The rest is history.
When John Henry bought the Red Sox in 2001, he was a billionaire hedge fund manager. He partnered with Tom Werner, who was a television executive. Even though Henry had owned a stake in the Florida Marlins, he was not a “baseball guy.” His master stroke was bringing in Larry Lucchino to the ownership group. Larry had been in baseball operations since 1988 with the Baltimore Orioles and San Diego Padres. He had mentored these two Brookline kids named Theo Epstein and Sam Kennedy since the mid-90s. He installed Epstein as the general manager, and again, the rest is history.
So, as you can see, it’s all about hiring the right people to run your team. Post 2018, both the Red Sox and Patriots fell on hard times. Tom Brady left after the 2019 season and Belichick struggled to win. Kraft had a hard decision to make but he made the right one, letting Bill go. After one disastrous decision to hire Jerrod Mayo as head coach, he realized his mistake and shifted gears quickly, hiring Mike Vrabel. That is the sign of a smart owner, correcting bad decisions. Even though they lost the Super Bowl this year, the team is obviously on the right track.
For the Red Sox, something happened in 2019. Major League Baseball authorized the investment of private equity firms in MLB clubs. Henry moved quickly to sell minority shares of FSG to Redbird Capital. This is very well documented in a recent Joon Lee piece:
Most people think this is where John Henry stopped prioritizing winning and shifted his focus completely to making money. FSG now owned several sports clubs across the globe and was raking in the dough.
After leading the Red Sox to a championship in 2018, Dave Dombrowski was fired in 2019 while the team had a winning record. I document what happened next in an article I wrote last year:
Sam Kennedy became the guy that John Henry trusted with the team. Sam was now fully in charge of all team operations. Sam was allowed to find a replacement for Dombrowski and created a new title, Chief Baseball Officer, reporting directly to him. Sam has made two CBO hires, both disastrous in my opinion. In six full seasons under Chaim Bloom and Craig Breslow, the Red Sox are 442-428 with two playoff appearances. 2026 is starting out in a devastating fashion and the problems are all directly related to Breslow’s mismanagement of the roster. The Red Sox have not fielded anything close to a championship caliber team since Dombrowski left.
John Henry, you have one job, and that is to change the leadership of the baseball team. I’m sure Henry’s first instinct will be to have Sam Kennedy lead the search for a third CBO, but that would be a bad decision. Kennedy has shown that he does not have what it takes to hire an effective leader of a baseball team. In the business world, if one of your leaders makes two terrible decisions, do you give them a third? Last year, I made the case for Theo, and I think that case remains strong today:
Theo Epstein has proven that he can not only build an effective front office, but that he can also provide a vision for the organization. This organizational philosophy reaches all corners of the club, including scouting, drafting, and minor league development. The Red Sox have failed in all these areas since Kennedy took over the team. Surely, this must be clear to Henry now, but the question remains does John Henry care about winning? He and Tom Werner have attended many games at Fenway this season. I don’t think this is a coincidence. Something is brewing. He obviously did not take kindly to those “Sell The Team” chants.
So, what’s up John? You are the greatest owner the Red Sox have ever had. It only took Bob Kraft one year to recognize his mistake and course correct, and the results speak for themselves. It’s been 8 years. It’s time to show Red Sox Nation you give a damn. If not Theo, find another effective leader to rebuild the front office and the team. Otherwise, as the fans have been saying, “Sell The Team.”