He may be worth $1.1 billion, but it’s no fun being John Henry right now.

A few years ago, he was considered the smartest owner in baseball. He had not only delivered the Boston Red Sox their first World Series victory since 1918. He presided over a magical sports kingdom, Red Sox Nation, whose proud, giddy citizens felt blessed for the opportunity to pay full freight for an “obstructed view” ticket, which is to say a hard seat behind a giant metal pole.

In the flush of his Red Sox success, Henry bought another storied sports franchise that was down on its luck: the Liverpool Football Club. He was hailed there as a savior, too, and not just because of the miracle he had worked in Boston. The team’s previous owner, the Texas billionaire Tom Hicks, was about as popular in the U.K. as King Richard III or Mitt Romney.

The parallels between the two franchises are striking. Both inhabit historic venues: Fenway and Anfield. Both share a sense of inadequacy, of forever playing in the shadow of their bigger, richer rival (in Boston, of course, that is the New York Yankees; in Liverpool, it is Manchester United). Liverpool fans might not have been as desperate for a trophy as Boston fans when Henry arrived, but a similar angst prevailed.

Henry had dealt with just such a situation before. He could do it again.

Continental Messes

Instead, he has made a mess of two different teams in two different sports on two different continents. The Red Sox are in the basement of the American League East, and Liverpool is off to its worst start since “Love Me Do.” Henry is no longer seen as a genius but as just another rich, out-of-touch, out-of-town owner who has lost the faith of his teams’ fans and the reverence of the sports-business community.

What went wrong, and can Henry fix it?

On the most basic level, he spent too much money, too recklessly. I’ve written about the stupidity of the huge, long-term contracts the Red Sox made a habit of doling out to veterans like Adrian Gonzalez and Carl Crawford. In Henry’s first year in Liverpool, the club broke its transfer-fee record twice within a matter of hours -- most notably on English striker Andy Carroll, who wound up scoring just 11 goals in 58 games.

Henry is now tacking back, and hard. He dumped $252 million in Red Sox contracts on the Dodgers. In Liverpool he not only loaned out Carroll to a competing team for the season, but also opted not to replace him with another expensive striker, offering a meager 4 million pounds ($6.4 million) for American star Clint Dempsey.

Henry seems to be telling us something: He’s done trying to buy championships, and instead will return to the strategy of talent development and bargain hunting that made the Red Sox successful in the first place.

Actually, Henry doesn’t just seem to be telling us that; he is telling us. In this week’s Sports Illustrated, Tom Verducci quotes Henry saying that the Red Sox implosion has made him less inclined to invest in high-priced free agents. And in a letter issued recently to Liverpool supporters, Henry vows to “never again waste resources on inflated transfer fees and unrealistic wages.” In other words, he is getting back to his “Moneyball” roots.

Only it might not be so simple.

In 2002, the year Henry bought the Sox and a year before Michael Lewis’s book about the Oakland Athletics was published, the notion that you could rely on under-appreciated statistics as opposed to a scout’s subjective judgment to evaluate a baseball player was innovative thinking. Now it’s conventional wisdom.

No Moneysoccerball

New analytics are coming to soccer, too, but it’s hard to believe they will transform the game as radically as they transformed baseball -- for one simple reason: In baseball, players may be part of a team, but they work in isolation. Not so in soccer, which makes each individual’s performance far more difficult to predict.

Henry should know this better than anyone. In Liverpool, he hired and then fired the Billy Beane of the English Premier League, Damien Comolli, who signed a few expensive and ultimately disappointing players in part because of their success in “creating chances.”

The problem is that while Henry may be determined to stop spending recklessly, the teams that succeed in the Premier League are generally the teams that spend recklessly. They just spend it on better players than Liverpool has.

If Henry doesn’t want to compete for talent with oil sheikhs and debt-happy American corporate raiders -- see, for example, the Glazer family, which owns Manchester United -- his options are limited. He can continue to subsidize the team’s losses with his Red Sox TV revenue while trying to build another Arsenal (which, like a mutant superhero, seems somehow capable of perpetually reconstituting itself after losing seemingly irreplaceable parts). He can hope that the Premier League finally imposes some spending restrictions on its teams. Or he can go have a last pint at Arkles and sell the club before Liverpool’s supporters are once again burning U.S. flags at Anfield.

(Jonathan Mahler is a sports columnist for Bloomberg View. A long-time contributor to the New York Times Magazine, he is the author of the best-selling “Ladies and Gentlemen, the Bronx Is Burning,” “The Challenge,” and “Death Comes to Happy Valley.” The opinions expressed are his own.)

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To contact the writer of this article: Jonathan Mahler at jmahler11@bloomberg.net or @jonathanmahler on Twitter.

To contact the editor responsible for this article: Michael Newman at mnewman43@bloomberg.net.