Emailing with John Henry

Given the mind-boggling, globe-trotting schedule of John Henry, you can understand his reluctance to submit to a sit-down interview. But he did agree to answer a series of questions, and to be honest, that was actually preferable since it would give him a chance to open up at his own leisure. What you are about to read is a slightly abridged version of our Q and A, in which the Qs are softballs -- thrown on tiptoes -- and the As are rattled off the Green Monster.

WULF: What do you consider your proudest achievement in sports?

HENRY: I would have to say it's winning a second World Series in 2007. Winning in 2004 was heart-rending -- deeply emotional -- because Sox fans had waited so long and had gotten used to finishing second so painfully over those 86 years. Some people even thought the club was cursed.

But for those of us in the organization, knowing how hard it is to prevail in baseball's postseason, the second championship in 2007 proved that we had the right people in place and the right philosophy. We had often been criticized as too heavily statistics-based. People didn't realize how strong we were in scouting and player development until so many of our young players starred in that postseason. We feel we have an opportunity in 2011 to be a special team again.

WULF: Since you've taken over the Red Sox, you've had many causes to celebrate, and relatively few disappointments. What was your happiest celebration, and conversely, what has been your deepest disappointment?

HENRY: Well, 2004 was quite a celebration. 86 years was a long time. It really began after we had won the last four games for the American League championship, culminating in going into Yankee Stadium for Game Seven. There had never been a comeback in baseball postseason after losing the first three games. That celebration picked up again at the end of the World Series and we fulfilled a promise to take the World Series trophy into every town in Massachusetts -- hundreds of towns as well as communities throughout New England. We were exhausted when the 2005 season began.

Our greatest disappointments were the very strong teams we had in 2006 and 2010. Those two teams were decimated by injuries. Injuries are a part of the sport, but those were two really strong clubs. It's also been disappointing how baseball works economically, but the advantage has been that it has caused us to branch out into other sports.

WULF: On the one hand, Red Sox fans are loyal, knowledgeable and passionate, and that is part and parcel of the team's success. On the other hand, they can be so demanding that they can seem ungrateful. How closely do you listen to them?

HENRY: I honestly haven't met ungrateful Sox fans. The most common thing that is said to me is, "Thank you." And it's usually said with a palpable seriousness. They're grateful that we were able to save Fenway and many are pleased with how vibrant Fenway is every night. But it's really the fans selling out the park every night that creates the magic and vibrancy that is so evident. And of course Tom and Larry have spent 10 years listening hard and working hard to bring all of this about.

They're also grateful that we're able to spend enough to compete with the Yankees. But again, that's because of their support, the support of our under-acknowledged partners and our sponsors. They're grateful that we have put solid teams together every year and have a chance to win every year. But they give us that ability.

WULF: How closely do you read the Boston writers?

HENRY: I don't read that much written opinion about the Sox because there's enough to keep track of internally, and there are so many bloggers and websites. But the Sox are blessed with knowledgeable writers whose jobs get harder every year. It seems like we are less and less controversial every year -- thankfully.

WULF: Does your organization have an overriding philosophy?

HENRY: Trying to win championships in professional sports is very, very difficult. You have the best of the best in each sport competing on and off the field at the highest levels. You have approximately 30 organizations in each sport in the U.S. trying to accomplish one thing -- win the last game that is played in your sport that year. But only 1 out of those 30 will be successful.

So our philosophy is that you can leave no stone unturned in trying to win. You have to be bold, inventive and most of all judicious in every area of a sport. To be judicious requires an intense study of all of the factors -- old, current and future factors that are going to determine your success. Then implementation is dependent on how effective your organization is. You can't be successful on the field without being very successful off the field. All of that requires tremendous commitment from the people of your organization; it takes sacrifice. But the rewards are immense, and you feel yourself part of something much larger than yourself. We do.

There is a certain discipline that emerges out of this shared commitment and a tremendous camaraderie unfolds that nourishes the spirit. The rewards we enjoy are not possible in most industries.

Finally, in the modern world, you can't win in any sport without heavily concentrating on revenue generation. You have to be relentless in that regard if you are going to be able to afford the kind of players you need to compete at the highest level. There simply is no way around that.

WULF: Was there an epiphany, an aha moment, so to speak, that motivated you to invest in 1) the Red Sox; 2) Roush Racing; 3) Liverpool FC?

1. If you are a sports fan and have the chance to buy the Boston Red Sox and you can afford it -- I think every red-blooded American male would say, "Where do I sign?" We know every morning as we start work that what we do matters to millions. And as you pointed out previously, it matters greatly to our fans. We see the same passion with Liverpool fans around the world. You want to be involved in something that matters to people, touches them profoundly.

2. iRacing is what led me to Roush Fenway Racing. It's a passion I share with Dale Earnhardt Jr. and a number of other enthusiasts. Dale and I have been doing everything we can to support Dave Kaemmer's genius in bring the racing community together on the Internet ... [with] a simulation so real that it has become a tool for racing professionals.

One reason investing in Roush appealed to Fenway was our frustration over baseball's economic system -- we began to look for revenues outside of baseball. As an example, we own Fenway Park, we invested more than $250,000,000 in the park over the past 10 years, and yet when the 100th anniversary of Fenway approached for 2012, we found we couldn't even produce a book about it. MLB, through its agency agreement, has an exclusive license to the name and photographs of Fenway. We had to produce a book through MLB and pay them to do so.

Another reason was that Jack Roush and I really hit it off when I went to see him about getting involved at the highest level of NASCAR. It has an entrepreneurial structure, and Jack is one of America's best entrepreneurs. So when we met, we found we shared Mid-western values and were kindred spirits competitively. Jack burns to compete. He's survived terrible automobile and plane crashes and is still flying and driving to racetracks every weekend, burning to win.

3. This was the rarest of opportunities. How often do you get the chance to be a part of the most historic club in the world's most popular sport? When this opportunity was presented to us, we found that Liverpool Football Club is probably the most beloved football club in the world. There is a passion for this amazing club that is every bit as deep as what we have experienced with the Red Sox. They are a part of the biggest rivalry in sports. Manchester United and Liverpool meet twice a year in the English Premier League, and the viewership for those matches is a multiple of America's biggest television event -- the Super Bowl. We thought Yankees/Red Sox was big, and it is very, very big in the U.S. However, United/Liverpool is global.

So the chance to be a part of both was mind-boggling to us and remains so.

There were a number of parallels to what we faced when we arrived in Boston. For one, Liverpool has Anfield -- an analogue to Fenway in that it's over 100 years old and 30,000 seats smaller than Manchester United's stadium. Anfield is perhaps the most sacred ground in football. So we have to be just as careful there as we were in Boston. Also the rivalry has been one-sided much like Sox/Yankees before we arrived. And Liverpool was used to winning titles in Europe -- particularly in England -- but hasn't won the Premier League in its 20 years of existence. So we saw a tremendous challenge within the context of a second historic club.

Another major reason was that we felt stifled in baseball by all of the restrictions outside of New England. Liverpool is a global phenomenon that presented an opportunity for all of the creative people in Fenway Sports Group. We've driven revenues as far as baseball will allow and here was an opportunity to compete globally in a league without borders. We saw the challenge of letting Liverpool fans around the world who care so much about their club know that their club and organization care about them as well. We know their number one agenda is silverware -- trophies.

WULF: Friends, colleagues and employees often praise you for your sense of empathy and decency. Where do you think that quality came from?

HENRY: How about a different question? Look at the people I work with. They are all people you can learn from -- not just about baseball and football, but in how exemplary their lives are. Their work is an affair of the heart and a responsibility they feel deeply.

I'd prefer a question like this: Who were your major influences?

Joseph Campbell had an impact on my life when he said, "If you follow your bliss, you put yourself on a kind of track that has been there all the while, waiting for you, and the life that you ought to be living is the one you are living. Wherever you are -- if you are following your bliss, you are enjoying that refreshment, that life within you, all the time."

I always give that advice to young people because it has served me so well. With the Red Sox, Roush Fenway, Liverpool and iRacing.com, I'm following my bliss. That's what led me into the financial world. I started John W. Henry & Company because I enjoyed applying mathematics to markets, and it was a profound challenge that resonated within me.

I also spent some time with Jiddu Krishnamurti who was such an iconoclast that he taught me to pay attention to "what is" rather than what should be. That enabled me push aside my opinions in financial markets and in sports in favor of paying attention to "what is." We spend so much of our lives immersed in thought, immersed in victimization -- if you really pay attention to "what is" there is a significant intelligence that operates and enables you to improve almost any situation.

WULF: How would you characterize your management style?

HENRY: I'm a tough manager. I question almost every assumption in what are hopefully pragmatic ways. The more you question, the more you learn, and the more the person you are questioning learns. But it is only productive if you are both completely focused on what you are trying to accomplish. More than anything else, management is a question of ensuring you have the right people in place. and they have the resources necessary to be successful.

WULF: Given your kaleidoscope of interests, what is your typical day like?

HENRY: I spend a lot of time working via email and have spent a lot of time researching football over the past year. I try to watch all 10 EPL matches each week as a way of learning the sport. I watch Barcelona and Real Madrid as well. I'm just now beginning to understand why the sport is so different in warmer and colder climates.

I watch 162 Sox games if you don't include the postseason. It's so difficult to wait a week for the next Liverpool match. I prefer the daily ups and downs to weekly ups and downs. Tom [Werner] and I spend more time on league issues in baseball than anything else unfortunately. Thankfully we have 81 magical home games each year. Each night at Fenway the games are meaningful, with a packed house, an intensity and energy that mirrors the postseason, and there is this profound sense that these nights are somehow at the very core of the fabric of these fabulous yet intimate New England summers.

WULF: Can you give me some idea of your ports of call in the last six months? I don't mean to pry, but you do seem to get around.

HENRY: Ouch, I get tired just thinking about that question.

Steve Wulf is a senior writer for ESPN The Magazine.