Theo Epstein was the fresh-faced, newly hired assistant GM of the Red Sox in 2002 when he started getting lengthy, late-night emails from principal owner John Henry, whose curiosity about the way the baseball operations department valued players and the hidden world of baseball math appeared to be boundless.
“It was a turnaround operation, so we were working late all the time,” said Epstein, who was promoted to GM the following year and helped bring the Red Sox their “curse-breaking” World Series win in 2004. “I’d be in the office, get an email from John and read through [the] whole thing. I figured, it’s late and I’m here. I may as well get credit for being here. I’m going to reply real quick.
“And then another one would come in.”
Henry’s emails revealed a fascination with then-cutting-edge metrics and an appetite to rely more on them when valuing players and considering moves.
His dedication to figures over feel was never more evident than when he approved Epstein’s request to trade shortstop Nomar Garciaparra, a face-of-the-franchise type whose metrics didn’t support his station. Henry didn’t bring up the public hit they would take. He wanted to know how Garciaparra’s defensive deficiencies were affecting the club, and what a replacement might look like.
“Sometimes there are business reasons to do things, and I was always adamant about the commercial aspect never interfering with the baseball aspect,” Henry said, explaining an approach he has clung to since buying the team. “You don’t want somebody signing a star who is washed up to sell tickets. You don’t want to make trades to energize the fan base.”
Henry told Epstein that if a Garciaparra trade penciled out, he should make it. When they did, the blowback was intense.
“I remember sitting in the office after making that trade, literally all by myself, thinking about the consequences of it,” Epstein said. “And the one person who called was John.”
“I was just thinking through this,” Henry began, “and, man, you must feel like the loneliest guy in the world right now.”
“It was exactly like I felt,” Epstein said.
This is the difficult-to-resolve dichotomy that is John Henry.
There is the seemingly obsessive, numbers-crunching quant, dissecting trends and firing off overnight emails, curious about the thinking that underpins every decision and the minutiae of how everything works.
And then there is the gentle, quietly enthusiastic leader who is more likely to listen than speak and to query than command, winning over the hearts and minds of alpha types across sports and throughout his own organization.
“He gave some amazing speeches this weekend, but that’s not normally how he leads,” Fenway Sports Group General Counsel Ed Weiss said as the group’s partners meetings wound down this spring. “He normally leads by knowing more about something than anybody else, being more forward thinking than anybody else, and then by sending emails at 3 and 4 in the morning.”
Mike Gordon, the FSG president and stakeholder who shares Henry’s fascination with numbers and background as a fund manager, is one of many who points to his listening skills as a differentiator.
“John is a great listener, and I mean that as a discreet, identifiable skill,” Gordon said. “He takes a lot in. He processes. And then he will offer an opinion. Everyone stops and takes in what he has to say. And he’s almost always right. He’s not a domineering presence. But he’s very enthusiastic about what we do, regardless of the topic. And he’s very open-minded. That’s an analog to being a good listener.
“He is not set or hardened or entrenched in a point of view. A lot of people, especially people who have had that kind of success, get to this point and they fit facts to support a conclusion. He really has a very open, almost Socratic way of processing things.”
It is both a hallmark of Henry’s decision-making process within FSG and his superpower when advocating on his teams’ behalf.
“Like a lot of very effective people, John is one who wants to understand the context before he weighs in,” said MLB Commissioner Rob Manfred. “Having the patience to hear the room before you speak has been something that has served John really well, because he understands whether people agree or disagree with him. He understands better where other people are. And it puts him in a position to make very effective points.”
Many who have sat around a conference table or on a board call with Henry share stories of him patiently listening and politely questioning — and then sometimes exiting without rendering a definitive decision, leaving them to determine, or perhaps decode, it on their own.
Julie Swinehart, who joined FSG as CFO four years ago after filling that role at publicly traded companies, recalled a meeting in which Henry asked a few questions at the start of a 30-slide presentation to review a potential investment, then left before it could resume.
“Well, we’re approved,” Kennedy said, adjourning.
“I’ve never seen someone who can motivate so many people by not dominating a conversation,” Swinehart said. “There’s not micromanaging or mandates or orders, but you know, and then you coordinate with your colleagues to make sure everyone heard the same thing.”
Now an adviser to Henry and FSG partner, Epstein said he has seen the gap between the deep-in-thought analytical thinker and the collaborative, people-focused leader narrow since Henry married the former Linda Pizzuti in 2009.
“Linda has been great for him, helping him share that passion with people,” Epstein said. “He’s enjoying himself a lot more and smiling a lot more. It’s great to see.”
Listen Up …
“He doesn’t speak the most in the room. He doesn’t speak the loudest in the room. But he frequently gets to the crux of the issue better than anyone else in the room.”
— Theo Epstein, FSG adviser and former Red Sox GM
“He doesn’t feel a need to fill the air with his commentary. He asks thoughtful questions, and when he makes points they’re reasoned points. They’re not simply advocating for his point of view.”
— Milwaukee Brewers owner Mark Attanasio
“There are some people who think they can learn while they’re listening to themselves. John’s not that type. He doesn’t keep quiet and listen because he’s shy. He listens because he wants to learn from what people are saying and evaluate what they’re saying.”
— Chicago White Sox owner Jerry Reinsdorf
