Nine years ago this month, John Henry was driving around Boston and listening to a local sports radio show as the hosts were picking apart the management of the Red Sox, the baseball club whose season had just collapsed in epic fashion.
Mr Henry, the team’s principal owner, drove directly to the studio, where co-host Michael Felger was so flustered he stumbled over the introduction of his surprise guest.
“John, tuh-whu-do-we-own, uh, to what do we owe the pleasure?” he asked, gulping.
“Well,” Mr Henry replied, calmly, “when you’re misleading the public, you know, you should be challenged on some of the things you’re saying.”
Mr Henry was, at that point, a self-made billionaire in commodities trading, owner of Boston’s beloved baseball franchise for nearly a decade, and had completed one season as owner of Liverpool Football Club. The hour-plus radio conversation that followed touched on a range of topics across his sports empire, from management to spending concerns to player signings and media coverage.
But the nature of the impromptu appearance itself was more revealing about Mr Henry than the sum of his individual answers: a passionate owner who deals in blunt facts, typical of a grizzled trading veteran.
A blend of both traditional and modern archetypes of sports ownership, Mr Henry is both an independently wealthy, mostly private figure content to enjoy his trophy assets and a markets savant with an eye for maximising returns.
That would explain, in part, his recent discussions with RedBall Acquisition Corp, the blank cheque company steered by Moneyball manager Billy Beane, about the possibility of a public listing for Mr Henry’s Fenway Sports Group that would also allow the current owner to remain in control of his clubs.
“John Henry clearly is an unusual owner,” said Paul Finkelman, president of Gratz College and a baseball historian. “On one level he fits the bill of a traditional baseball owner, a guy who made a lot of money and is able to buy a team. However, he is also somebody who is a brilliant and very sophisticated investor.”
Born in Illinois and raised on a family farm in Arkansas, Mr Henry, 71, made his fortune as a trader of commodities futures at a firm he founded. Friends, former associates and historians like Mr Finkelman describe him as a groundbreaking numbers genius.
“The old-fashioned way of hiring baseball players was: ‘does he look like a baseball player?'” Mr Finkelman said. The two people who brought a numbers-driven approach to the sport “were Billy Beane and John Henry”.
Ted Parkhill, managing partner of Incline Investment Advisors, worked at John W. Henry & Company from 2001 to 2007, an experience which he said was “completely career-changing”.
At a time when other people in the markets were using hazy forecasts to imagine the future, Mr Henry’s approach to using data analytics was a novelty.
“As he put it, he never had a better crystal ball than anyone else,” Mr Parkhill said. The firm “was very data driven. He was one of the original quantitative investment guys.”
The results of Mr Henry’s stewardship speak for themselves: he delivered championship trophies to two elite clubs after decades-long droughts. Liverpool won the Champions League and the Premiership in back-to-back seasons, re-establishing itself at the pinnacle of English football. In 2004, the Red Sox brought home their first World Series trophy in 86 years, and three more since.
Dave McGillivray, race director of the Boston Marathon and a life-long Red Sox fan, said Mr Henry’s leadership “changed the culture of spectators of Boston sports. The jinx is gone. We’re back.”
Could Mr Henry yield a similar kind of magic with a listing of Fenway Sports? There is no certainty that discussions with RedBall will lead to a deal, and people briefed on the matter say it remains unclear if Major League Baseball would approve a direct public listing of a franchise. (The Atlanta Braves, owned by Liberty Media, are a rare exception, in part because their business is not core to the media conglomerate’s operations as a whole.)
According to one person who knows Mr Henry well, a more plausible scenario could entail breaking up Fenway Sports Group and keeping the Red Sox private while listing Liverpool on the open market. He is an avowed baseball fan but Mr Henry’s interest in Liverpool is more financial than emotional. “I think he wants to make money,” the person said.
A spokeswoman for Mr Henry disputed that assessment. Mr Henry declined to comment.
Mr Henry’s reticence to explain his actions is consistent. He might have been eager to get on the radio in 2011 to interrupt his critics, but not necessarily to offer deep insight of his own. The show’s hosts pressed him to acknowledge that he had poured in $300m to the Red Sox to soothe fans’ concerns that he would be channelling too much of his money to his new football club.
“I said we spent,” Mr Henry said. “I didn’t say anything about the reason.”