Fuelled by a mixture of cheap debt and skillful financial engineering, the industry reached its recent high watermark in the spring of 2007, months before the financial crisis erupted.
Instead, Henry comes from the world of futures trading and appears to keep his company lean.
A handful of traders run his future business John W Henry & Company's computer trading programmes at its head office in Boca Raton, Florida.
When Henry, alongside Larry Lucchino and Tom Werner, won the fight for the Boston Red Sox in early 2002, it’s believed that their $660m offer was not even the highest of the six bids on the table.
But the Yawkey Trust, which controlled the club following the death of Thomas Yawkey – who had snapped the team up for $1.2m in the depths of the Great Depression in 1933 – liked the group’s plans for a club whose struggles on the field were hampering its commercial development off it.
While little is known of the finances of J W Henry as it’s a private company, its value is likely to have diminished in the past five years as larger rivals such as London-based Winton Capital and Aspect grab larger market shares.
However, his ownership of the Boston Red Sox suggests Henry, Lucchino and Werner know how to increase the value of a brand — something that will prove key given Liverpool’s global reach.
New England Sports Ventures has overseen a doubling in the value of the Red Sox from $426m - that valuation excluded the debt it assumed when buying the club - in 2002, to $870m this year, according to Forbes data. In the same period, the club has gone from nursing an $11m loss to being $40m in the black.
The Red Sox have overtaken the New York Mets and LA Dodgers in Forbes’s annual Major League valuation table and are now only second to the New York Yankees, their closest rivals.
“They have transformed a mundane franchise into one of the most successful in the business,” according to a leading sports banker, who has worked with Henry.
“They have diversified their revenues by selling advertising and other spin-offs, and improving the concessions at Fenway Park,” he said.
“They also enhanced their media exposure and improved the experience in the stadium. You cannot get a seat at Fenway Park any more.”
He said he was confident the tycoon could replicate the success at Liverpool but that this would require substantial investment.
And serious questions remain for Henry, including the possible building of a new stadium – something that Hicks and co-owner George Gillett never managed.
“There are big questions,” the financier said. “Liverpool needs a new stadium, which would cost about £700 million.
“And the success of the product starts on the field. You need to build a very good team and there is no limit to how much you can spend on players.”
While not a financier reliant on debt, Henry is still likely to find restoring Liverpool’s fortunes on and off the pitch will require him to dig heavily into his pockets.
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