Both are ardent fans who dipped into their fortunes to resuscitate storied European football franchises, though each betrays a markedly different game face. Only one, for example, is the type to jump into a fountain amid a crowd of delirious fans to celebrate an improbable victory.
Now, in an unlikely turn of events, the two Boston businessmen — and friends — are facing off against each other in stadiums on the other side of the Atlantic in one of the richest sporting contests in the world, one that dwarfs that silly little Super Bowl.
On Tuesday, Liverpool FC of England, owned by John Henry and a team of Boston business executives, faces AS Roma of Italy, owned by James Pallotta and a different team of Boston business executives, in the semifinals of the UEFA Champions League, perhaps the world’s greatest sporting tournament.
Introducing “the Boston Derby” — that’s “dar-be,” for you readers who still call it “soccer.”
“This is a great story line — the two Boston ownerships facing each other,” said Rich D’Amore, a local owner of AS Roma. “I’ll take this.”
Henry and Pallotta are better known in these parts for their other sports pursuits: Pallotta as a part-owner of the Celtics and member of its executive committee, Henry as the principal owner of the Boston Red Sox. (Henry is also the owner of The Boston Globe.)
The first leg of the two-game semifinal is in Liverpool at historic Anfield stadium. The second, on May 2, is at Stadio Olimpico, scene of Roma’s greatest accomplishment so far under the Boston ownership, the miraculous victory over Lionel Messi’s Barcelona on April 10 to advance to the semifinals.
That astonishing feat prompted Pallotta, celebrating in a crush of fans that night in the Piazza del Popolo, to inelegantly flip backwards into the Fontana dei Leoni in what could be the most expensive swim in history.
This is the furthest Roma has ever advanced in the Champions League, a tournament of Europe’s best soccer clubs, while it’s Liverpool’s deepest run since a 2007 loss in the final. The teams met in the final of a previous European cup, in 1984, which Liverpool won on penalty kicks.
The winner will advance to the finals, possibly against soccer superstar Cristiano Ronaldo and Real Madrid. And a trophy would undoubtedly elevate either Henry or Pallotta to knighthood, if not sainthood, in his adopted soccer home.
If, as some of the more giddy oddsmakers in England are wagering, the crown goes to Liverpool, is it possible Henry pulls a Pallotta with a swan into a fountain in that city?
Pallotta, for one, deftly sidestepped a suggestion to challenge his opposite number.
“He’s a little more measured. Me, I’m Italian,” said Pallotta, who grew up in Boston’s North End and often has spirited chats with fans on the streets of Rome. “I just feel comfortable having those conversations with people — it’s the way I’m built. As it turns out — that openness — our fans like it a lot.”
Even when it proves costly. Frolicking in Rome’s historic fountains is proibito, with a fine of nearly $600. Pallotta cheerfully paid up during a meeting with the mayor of Rome the next morning — and for good measure, donated some $280,000 to upgrade another old fountain.
The more reserved Henry wouldn’t bite on the fountain dare, either, focusing instead on how “exciting” it is for Boston to have two “iconic sports clubs” in the Champions League.
“Jimmy and I have known each other almost since I arrived in Boston more than 16 years ago. . . . There are few Bostonians who have done more than Jimmy has to support the most important causes in our community,” he said.
So much for a little pregame trash-talking.
The stakes are enormous, beyond soccer glory. Their deep runs in this elite tournament have reportedly earned Roma more than 90 million euros ($110.6 million) so far, and Liverpool 66 million ($81.1 million); and winning the trophy will bring additional millions.
The list of Roma and Liverpool investors reads like a Business Round Table of Boston. In addition to D’Amore, a partner at North Bridge Venture Partners, Roma claims Paul Edgerley of Bain Capital, also part-owner of the Boston Celtics; David Gross-Loh, also of Bain Capital; former Aetna and Caesars casino executive Gary Loveman; Tom Roberts of Summit Partners; and Mike Ruane of TA Realty. Bruins great Cam Neely is on Roma’s board.
For Liverpool, the Fenway Sports Group also includes Thomas Werner, the television producer and screenwriter who chairs both Liverpool and the Red Sox; and investor Seth Klarman of the Baupost Group; as well as Frank Resnek, Henry McCance, Herb Wagner, and Mike Gordon, who runs Liverpool day-to-day.
“It’s fun to have a rivalry, where you really are a mile apart from the different owners,” said Edgerley.
It took a few years, but that business firepower is having an effect.
Like the Celtics and the Red Sox, both were celebrated clubs that had fallen from atop their sport when they were bought by the Boston groups — Liverpool in 2010 and Roma in 2011. They are once again consistent — and feared — competitors.
David Ginsberg, who also has an ownership in the Fenway Sports Group, has worked for both Henry and Pallotta, first as an executive at Fenway Sports and now by helping Roma build a new stadium.
“They’re both pretty serious about their sports. They both bring a unique combination of business acumen and passion for sports,” Ginsberg said. “It says something about Boston being a sports town. You don’t get there by accident.”
Adding to the frisson is the fact that arguably the best soccer player on the planet right now is Liverpool striker Mohamed Salah, who has scored 40 goals in all competitions this season, but who at this time last year was playing for . . . Roma.
At the player’s request, the club sent Salah to Liverpool during the offseason — for an initial fee of around 42 million euros ($51.6 million).
A week after the deal, Henry and Pallotta had lunch together at Quincy Market, and the subject of the Salah “bargain” came up.
“John said, ‘I cannot believe we paid you so much for Salah,’ ” Pallotta recalled. “I said, ‘Really? You should have paid us more.’ ”
So far, Henry has gotten the better end of the deal — in two ways. Pallotta picked up the lunch tab that day as well, “because he thought we were a little crazy in how much we paid for Mo,” Henry recalled. “Frankly, I thought it was a lot at the time, so I was very happy to have a free lunch.”
Until Tuesday, then.Milton J. Valencia can be reached at email@example.com. Follow him on Twitter @miltonvalencia. Andrew Caffrey can be reached at firstname.lastname@example.org. Follow him on Twitter @andrewcaffrey.