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Trying time for a quiet man

Henry’s analytical approach with Sox faces huge challenge

By Shira Springer
Globe Staff / October 16, 2011

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The magic happens in the early-morning quiet. That’s when Boston Red Sox principal owner John Henry’s mind starts to race, often taking him on tangents few others see and then off to his keyboard.

“He’s relentless with 4 a.m. e-mails,’’ says Mike Dee, a former Red Sox chief operating officer. “When you woke up and saw John Henry in your inbox, you knew it was going to be something good.’’

Henry’s late-night brain bursts run from grand visions to negotiating tactics to little things that bother only him.

Lately, however, his attention has turned to crisis management - and to something that bothers all of Red Sox Nation. After the Red Sox’ historic September collapse, Henry enters the most unsettled and unsettling period of his nearly 10-year ownership. His tenure and management style are facing withering attack.

General manager Theo Epstein and manager Terry Francona quickly made for the Fenway Park exits, with some of the players responsible for the ‘entitled’ culture Francona said he battled almost certain to follow.

What had once been a franchise with one of the shiniest images among professional sports franchises - a model for others, many would say - is suddenly riven by controversy and a media piñata. Even David Ortiz, the clutch-hitting, jovial face of the Red Sox, says he is tired of the Boston drama, threatening to join the New York Yankees.

If Henry, 62, was not already nocturnal by nature, a man who amassed billions by tracking market trends around the clock, the most recent Red Sox developments would surely leave him sleepless. And, he says, he does worry about it all.

“It’s my job to be accountable for everything that happens to the Red Sox,’’ Henry told the Globe, responding to questions via e-mail. “We were the best club in baseball until September. The fact that we didn’t make the playoffs is unacceptable.’’

He doesn’t see an organization in chaos, but rather one that needs to rebuild team chemistry and player accountability, regain the fans’ trust, and repair a battered brand. Faces in the clubhouse and front office will change, but Henry will stay true to his ownership philosophy and management style, say friends, current business partners, and former Red Sox executives.

He will still value statistics as an evaluational tool. He will try to think unconventionally and hire smart people, following the approach that has already brought him success in business and baseball. As a commodities trader who capitalizes on the volatility of financial markets, Henry knows how to ride out troubled times and finish ahead. He also knows every investor has a bad stretch from time to time, and the Red Sox are coming off a very bad stretch.

September “was a painful month for the fans,’’ says Henry. “That fact is etched upon my psyche. It will spur us on to ensure that we come back very strongly, get the right manager in place, and do the right things for this great club. When we failed and failed terribly to make the postseason this year, I felt deeply responsible. I take everything with this club personally, because the Sox are beloved by so many who have stuck by the Sox through every failure and every triumph.’’

In his time atop the Red Sox chain of command, Henry has been the pale, spotlight-shy ownership face of the team. Leading a group that paid $700 million for it, he was “over the moon’’ when he bought it with Red Sox chairman Tom Werner by his side and president Larry Lucchino on board. (The New York Times Co., owner of the Globe, was a co-investor; it has since reduced its stake.) Henry saw himself as a “caretaker’’ for all the club stood for and meant to New England.

And for years, all was good, very good, with two World Series titles, Fenway Park attendance records, and Fenway brand expansion into NASCAR and English football. But these days, with fan loyalty in question, Red Sox Nation turns to Henry and wonders if his interests in Roush Fenway Racing and English Premier League team Liverpool have diluted his focus on the Sox.

“The fact is that very few owners run their clubs day-to-day exclusively,’’ says Henry. “They usually run other companies. But Tom and I spend most of our waking hours working on ensuring these entities have the resources necessary to be champions, that we are adhering to sound business practices and philosophies as organizations and ensuring the right people run them.

“You wouldn’t want us making the baseball decisions, other than financial decisions. That’s not our expertise. But we do question and we are constantly looking for ways to improve everything.’’

Henry canceled a trip this weekend to Liverpool to take in yesterday’s match against rival Manchester United. A photo of Henry beside Miami Heat star and Liverpool minority stake owner LeBron James would have been another wrong message at the wrong time.

He clearly senses this is no time to further test the fans’ patience; they have reached their limit. Already predisposed to hand-wringing and to conjuring worst-case scenarios, many faithful now worry that the days of championship celebrations may be a long time returning.

But the view from the very top of the baseball pyramid is a little different.

“Henry, Werner, and Lucchino were the right people at the right time for the Red Sox franchise, and I still feel that way today,’’ says Major League Baseball commissioner Bud Selig. “Given their track record, they’ll do it again.’’

When Henry first arrived in town, in the winter of 2001-02, Patriots owner Robert Kraft offered the newcomer advice, particularly an education in the local sports scene and Boston fans. “We chatted a lot,’’ says Kraft, who respected the way Henry methodically tackled problems “almost like an engineer.’’

Kraft saw a personality with the best blend of skills for ownership-a careful nature combined with a willingness to make bold moves and commit capital. Kraft understands the challenges ahead for Henry.

“We’ve learned it’s harder to sustain success than it is to attain it,’’ says Kraft. “When you have success, you have a lot of different factions within your organization that think they’re the main reason for the success. It’s marketing. It’s sales. It’s managers. It’s general managers. It’s coaches. It’s players. That’s all natural. But when you have success, it becomes a more complicated management job to try to hold it together.’’

Or, to stop a free-fall.

Some have tried to infer from Henry’s frail-looking build, quiet demeanor, and even quieter voice that he may not have the personal toughness to address the challenge at hand. But some who know him, personally and professionally, believe Henry will find a way to manage the team through the furor.

“The way he thinks through issues is very much outside the box, refreshing,’’ says Werner. “I’m not going to compare John to Steve Jobs. But they share one thing in common. They are both very unconventional thinkers and see things sometimes in ways where people would say, ‘Well, they’re geniuses.’ . . . Part of it is John was a musician. Part of it is he’s an artist in some ways.’’

Werner cites the hiring of an inexperienced, untested 28-year-old Epstein and a restructuring of Liverpool management as examples of such outside-the-box thinking. In Liverpool, Henry put in place a director of football, the equivalent of a general manager, which rarely exists in the English Premier League. Dee cites Henry’s vision for the Fenway Sports Group, leveraging the Red Sox brand beyond baseball.

Henry can be unconventional, quirky, and impetuous. Impetuous is the word Werner used to describe him before his wedding to Linda Pizzuti Henry. Others might say impulsive. With 45 minutes to go before the ceremony, the bridegroom had a hankering for a hot dog. After they pulled in to a roadside stand, Henry, his best man Werner, and two others in tuxedos snapped a picture of the scene and sent it to the future bride.

Impetuous and impulsive both describe Henry on Friday, when he made an impromptu visit to local radio station 98.5-FM The Sports Hub to defend the state of the Red Sox. It was an uncharacteristic move for Henry, who prefers his interviews conducted via e-mail with the opportunity for carefully worded responses. The radio appearance turned combative at several points, showing an angry side of Henry rarely heard in public, and a caustic wit capable of effectively landing jabs.

It was the first time since the Red Sox failed to make the playoffs, losing a nine-game lead the last month of the season, that fans could hear how much he cared and shared their frustration, that the September collapse and its fallout had fired him up.

While Henry describes baseball as “an affair of the heart, and has been since I was a small boy’’ rooting for the St. Louis Cardinals, fans rarely see his passion. His competitiveness - a quality essential in driving this Midwestern farm boy with asthma to become a rock musician and then a phenomenally successful financier - is seldom displayed.

“He’s tenacious,’’ says Dee, now the Miami Dolphins CEO. “His quiet nature would sometimes confuse people. When he truly wants to get something done, he’ll put his mind to it and find a way to get it done. It’s not an accident that he’s in the position and the role he’s in.’’

In meetings with executives, Henry takes a quiet, calm, questioning, yet demanding approach. “You couldn’t give John an answer that was not grounded in the facts,’’ says Dee. “You had to be on your game.’’

Liverpool’s director of football, Damien Comolli, praised Henry’s “ability to listen,’’ to take in new ideas with an openness rare for owners. Werner said Henry “operates in a way of looking for consensus’’ with Red Sox decisions. Those who have worked with Henry says he is innately expert at juggling personalities, giving executives space to thrive in their roles.

One criticism of Henry’s management approach is that he prefers to avoid conflict and is sometimes inattentive to day-to-day details. This year, his critics say, too much latitude was given to his subordinate managers. And he was slow to step in as things went south.

That pattern has a precedent in his tenure. In October 2005, after the Chicago White Sox swept the Red Sox from the playoffs, Henry was not aware how discordant the relationship between Epstein and Lucchino had become, how trust had eroded.

Epstein resigned that Halloween and, to evade reporters, left Fenway in a gorilla suit. At a press conference later, Henry said, “Maybe I’m not fit to be principal owner of the Boston Red Sox.’’ Until now, it was the low point in his tenure as owner.

The team, of course, recovered from that acrimonious interlude and won another championship. Henry’s friends in the Boston business community say they expect he will find the right people to help him lead the team out of this hole, too.

“John is a great manager of people,’’ says friend Jack Connors, founder of the Hill Holliday ad agency and a local philanthropist. “He’s a world-class owner. He’s a great delegator. But what comes to mind now is that quote from Ronald Reagan. I think you might see a little more of the ‘trust, but verify’ for a while.’’

Henry’s basic management method is to gather bright people around him. He delights in engaging smart people on all manner of subjects. The books on his shelves are eclectic. He has been influenced by Eastern philosopher Jiddu Krishnamurti, who spoke against conformity and traditional thinking. He talks about Joseph Campbell and “The Power of Myth,’’ which discusses heroes, creation myths, and following your bliss.

“When you’ve got something to say to John or you want to deliver a point, he takes it on,’’ says Comolli. “He’s someone you can talk to, someone you can give ideas, and he will bounce back ideas. It is a fantasy ownership.’’

Part of the desire to branch out into auto racing was the intelligence of NASCAR icon Jack Roush. After reading the book “Men And Speed,’’ Henry called Roush to learn more about the race team.

Roush talks of a rewarding relationship with Henry and synergy with the Red Sox brand. In contract negotiations with drivers and crew chiefs, Roush has also seen Henry’s competitive side come out, wanting to get the best deal for the racing team.

“Do I think he’s taken on too much?’’ says Roush. “All of us who are entrepreneurs, who are challenged by the opportunities our activities present, should be aggressive. We should make sure not to waste a day.’’

Now, for Henry and the Red Sox, the need for aggressive action - for just the right 4 a.m. inspiration - has never been more pressing.

Shira Springer can be reached at

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