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John Henry a keen student of risk, reward

John Henry, who dropped out of college, caught rock ’n’ roll fever in the 1960s.

ASSOCIATED PRESS/FILE 2007

John Henry, who dropped out of college, caught rock ’n’ roll fever in the 1960s.

John W. Henry was a college dropout playing guitar in a rock band when his life took a sudden turn in the 1970s. The death of his father gave him control of the family’s soybean farm in Arkansas, a business that didn’t seem to suit him any better than being a rock ’n’ roller.

So he did something different. With a natural affinity for numbers, Henry used his growing knowledge of the soybean business to trade commodities, making a fortune that allowed him in time to become the principal owner of the Boston Red Sox.

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Now, Henry, 63, is making another unconventional move: taking on ownership of The Boston Globe, New England’s largest and most influential newspaper.

In a brief statement early Saturday, Henry said it would be premature to comment on his plans for the Globe, but said he felt strongly about its place in Boston. “This is a thriving, dynamic region that needs a strong, sustainable Boston Globe playing an integral role in the community’s long-term future,” Henry said.

In his different pursuits, Henry has earned a reputation as a smart businessman willing to make bold, risky bets — and winning many of them.

“He’s not the kind of person who’s going to . . . come in and hack everything to pieces and sell off the parts,” said Boston businessman Joseph O’Donnell, who in 2001 led a rival effort to buy the Red Sox. “He’s determined to do things his way, and he’s won two world championships, so it’s hard to argue he hasn’t been successful.”

After shutting his shrinking commodities firm last year, Henry focused his attention on Fenway Sports Group , which owns the Red Sox, a majority stake in the popular regional sports channel New England Sports Network, a successful NASCAR racing team, and a sports-marketing arm. In 2010, Henry made another big leap when his group paid $477 million for one of the most storied brands in soccer, England’s Liverpool FC.

Though technically a media veteran through his ownership of NESN, Henry’s ownership of the Globe marks his first foray into the mainstream news business. He has entered an agreement to buy the Globe from the New York Times Co. for $70 million in cash. The deal also includes BostonGlobe.com and Boston.com; the Worcester Telegram & Gazette newspaper and its website; the Globe’s direct mail business; and a 49 percent interest in the Metro Boston commuter newspaper.

Besides the obvious difficulties of running a struggling company in a volatile industry, Henry faces a challenge unique to this purchase: ensuring the Globe continues to provide objective coverage of his baseball team.

Like any sports owner, Henry has periodically chafed at the treatment of his team by local news media, and the Globe’s coverage of the Red Sox’s epic 2011 collapse particularly rankled him. He was upset that the Globe had opened a window into the personal life of former Sox manager Terry Francona when it reported that unnamed team sources were concerned the skipper’s failing marriage and use of painkillers had distracted him from his job during the season.

“It’s reprehensible that it was written about in the first place,” Henry said in a radio interview soon after the season’s end.

Jack Connors, a former advertising executive who also bid for the Globe, said he believes Henry will be sensitive to potential conflicts over sports coverage.

“I don’t think he’s going to dictate,” Connors said. “John is very analytical. He loves data and he loves modern technology, and I think you’ll see him want to make investments on the dot-com side.”

Boston Celtics co-owner Steve Pagliuca, an executive at Bain Capital and a friend of Henry’s, said Henry may be interested in a multimedia approach, involving NESN and Globe sports coverage. “There could be mutual benefits for the television property and the news operation to combine forces,’’ he said.

As for the newspaper’s mission outside of sports, Pagliuca said Henry will do the right thing for the Globe and its readers. “If you’re going to have a successful newspaper, it’s going to have to be balanced,’’ he said.

Henry typically keeps a low profile, seen more often in the personality pages than in news or political coverage because he and his wife are regulars at society and charitable events. His Twitter bio summarizes his philosophy: “It’s dangerous for execs to have opinions and humor.”

Although soft-spoken in public, Henry lives in high style, with a net worth of some $1.5 billion, according to Forbes magazine. He owns a 164-foot yacht, the Iroquois, and in 2009 married Linda Pizzuti, a 30-year-old real estate developer. He and Pizzuti have a toddler, and Henry has a daughter from his first marriage.

In 2007, he bought the Brookline home of Frank McCourt, the former owner of the Los Angeles Dodgers and unsuccessful Red Sox bidder, and promptly tore it down, building a 35,000-square-foot mansion.

The first quality friends and associates cite about Henry is his intelligence, that he is something of a business savant who seems to have an almost eerie ability to spot profitable opportunities.

“He’s prescient, he sees what other people don’t see,” said David D’Allessandro, the former chief executive of John Hancock Financial Services who was a Red Sox limited partner during Henry’s early tenure at the team.

“He’s both left and right brain, and extreme in both,” D’Allessandro said. “His mind works well both creatively and quantifiably. Most people have a narrow range.”

Others said Henry has a knack for finding talented executives to run his businesses, and letting them do their jobs. That said, Henry is firm in his convictions.

“He’s not a guy who backs down easily,” added O’Donnell, who for a period in 2001 discussed with Henry about teaming up to buy the Red Sox, only to walk away after lengthy, “tough” negotiations.

“I wouldn’t describe him as rigid,” O’Donnell said. “But he is single-minded. He’s got a strong mind, and it’s very hard to change his mind.”

Born in Quincy, Ill., to soybean farmers and raised mostly in Arkansas, Henry and his family moved to California when he was in high school, where he caught the rock ’n’ roll fever of the 1960s. He enrolled at a junior college, then shuttled among the campuses of the University of California, but never graduated.

At the time, he was more interested in touring with a pair of rock bands, Elysian Fields and Hillary, in which he played guitar. Like many a would-be male rock star in America, Henry told Bloomberg News in 2009, he wanted an adoring audience of “screaming women.”

Henry’s most notable collegiate accomplishment grew out of his aptitude for numbers. He and an instructor at UCLA published a paper about how to win at blackjack. He has said he was kicked out of Las Vegas casinos at age 22 for card counting.

Henry’s life took a more serious turn when his father died a few years later, leaving him in charge of the family soybean business. Rather than farming, Henry entered the highly speculative commodities business, which some in the industry say is closer to gambling than investing. But by 1981, Henry was winning more often than losing, using a method of statistical analysis he developed by studying decades of market prices.

In 2004, Henry told the Globe his approach was to focus on “what is, not what should be,” a lesson he learned in his early 20s after meeting Jiddu Krishnamurti, the late Eastern mystic who influenced millions.

The other key underpinning to that trading philosophy was a belief that humans, by nature, are trend followers, reacting mechanically to events, much as the clapping of one person in Fenway Park will typically be followed by another and another until it becomes widespread applause.

“Markets are really people,” observed Henry. “If you make a certain type of statement, you can make a pretty good prediction of how George Steinbrenner will react.”

At its peak, in 2006, his company had $2.5 billion under management. Its success gave Henry opportunities to invest in a lifelong passion for baseball that began during his childhood in Forrest City, Ark., where he listened to St. Louis Cardinals games on the radio. In 1998, with his company based in Boca Raton, he bought the Florida Marlins (now the Miami Marlins) for $150 million.

Owning a baseball team, Henry said then, is “a dream I’ve had for a long time.”

It wasn’t long, however, before Henry’s eye wandered toward one of the sport’s premier franchises, the Red Sox, which became available in 2000 when the club’s former chief executive, John Harrington, said he planned to sell the Yawkey Trust’s majority stake.

Henry led a successful bidding team that included the New York Times Co., from which he is now purchasing the Globe. The group bid $700 million for the Red Sox and 80 percent of the New England Sports Network, closing on the purchase in early 2002.

Within a few years, the Red Sox had won two World Series, ending an 86-year drought in dramatic fashion in 2004.

Henry and his partners built a reputation for spending huge sums to make the Red Sox competitive, splurging on superstar players, developing young talent in the minor league system, and making a series of upgrades to restore and modernize Fenway Park. The team’s success on the field fueled a record sellout streak of 820 games at Fenway that coincided with strong ratings on NESN during the team’s championship runs.

But the spending strategy backfired badly in 2011 when a roster thick with multimillionaires surrendered a late-season lead in the wild-card race and, mired in mediocrity and acrimony, finished out of the playoffs.

After struggling through another off year that included a sell-off of some of its biggest contracts, the Red Sox are again experiencing a revival, owning one of the best records in baseball and battling for first place.

Henry’s Liverpool investment, however, hasn’t been so clearly successful — yet. The club has not regained its perch atop the highly competitive English Premier League, though it has been steadily rebuilding under a new manager. In its annual listings of sports teams, Forbes ranks Liverpool as the 10th most valuable soccer franchise in the world, worth $651 million; the Red Sox, by contrast, are worth $1.3 billion.

Meanwhile, in the investment world, Henry’s commodities firm never recovered from the beating it took during the financial crisis. With most of his attention consumed by his sports business, Henry complained it had become too hard to make money in the investment trade. Assets at his firm had dwindled to less than $100 million, and in 2012, he announced that John W. Henry & Co. would stop managing client money.

He first emerged as a potential Globe buyer in June, when he and Bruins owner Jeremy Jacobs teamed up on a bid through NESN, 20 percent of which is owned by Jacobs’s Delaware North Cos. But their joint venture bid for the newspaper fell apart last month, leaving Henry to pursue the Globe on his own.

Casey Ross can be reached at cross@globe.com. Callum Borchers can be reached at callum.borchers@globe.com.

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