The Case for Theo

No More Half Measures, John

I know what you're thinking. There is no way in hell Theo Epstein is leaving his house in Connecticut where he reviews spreadsheets on FSG business performance and advises John Henry. He gets to have dinner with his family every night. He gets to drive the kids to school and attend their sporting events and school functions. You may be right, however I tend to think that a person who became one of the greatest baseball executives ever might still have the fire in his belly to do it all over again one last time.

Obviously, you don't pull out Breslow and slap Theo into the same position. Theo Epstein would need to be made CEO of the Red Sox. Sam Kennedy is CEO of FSG so one may assume that Theo would work for Sam. Nope, that's a non-starter for me and should be a non-starter for Theo as well. He's smart enough to know that Sam can't be anywhere near a baseball team given the mess he's made since 2019. For this to work, Theo must answer only to John Henry and have complete control of the team, including scouting, drafting, development, and major league operations. He must have full financial control, up to spending limits set by the owner. Unfortunately, there is no way around that, but Theo has successfully dealt with that before.

You may ask why John Henry would do that, and it's a good question. John Henry is living the dream, with a portfolio chock full of income producing assets. Sam Kennedy is his consigliere, ensuring all franchises in the portfolio maximize their potential revenue and minimize cost. Why would he just pluck the Red Sox away from Sam and give it back to Theo? Sure, the chances of fielding a winning team would increase, but would the profits increase as well? So, the big question becomes Does John Henry Still Care About Winning?

John Henry does still spend time in New England when he's not on his mega-yacht or across the pond in Liverpool taking pictures with the Premier League trophy. Some of his visits to Fenway or other public places haven't gone well for him in recent years. He was booed at Winter Weekend in 2023. He was also booed at the NHL Winter Classic at Fenway Park that same year. I think that didn't sit well with him and some think that led him to pony up the funds for Alex Bregman and Garrett Crochet. Does this indicate that he is now willing to spend on the Red Sox to make them champions again? Maybe.

So, those are the two big hurdles to make this happen. John Henry must want to win badly enough, and Theo Epstein must be willing to build another baseball team from the ground up. Next question, can Theo do it for a third time? Theo has proven that he is an astute evaluator of talent, not just on the field but in the front office. His "minions" in the early days have all gone on to have very good careers in baseball, including Jed Hoyer, Ben Cherington, Josh Byrnes, Jared Porter, and Zack Scott to name a few. Plus, many of the current members of the Red Sox front office came in under Epstein.

I think Theo could build an effective front office. The Red Sox seem to be relying too much on analytics these days and one of Theo's core principles is that analytics should be a tool to be used in conjunction with traditional scouting and minor league development. Theo has always been very transparent with his strategy. I remember when he was hired by the Cubs, he did a radio and TV tour laying out his vision and plan to make the Cubs a winner. Fans appreciated that, so much so that they lived through three long losing years before making it to the NLCS and eventually winning the World Series.

I know, this may all be a pipe dream but imagine if it were to happen. I think Red Sox fans would be thrilled. They might start buying merchandise again. They might start going to the ballpark again. Sam Kennedy has decimated the Red Sox and fans don't trust him anymore. One look at the comments on his recent Zoom call after the Devers trade will tell you that. Sam is a liar and a con man. This team needs someone the fans can trust. We need someone that has a proven track record of team building, decision making, and transparency. It's time for Theo to come home, and that home is Fenway Park.