Inside The Two Billionaire Owners Going Head-To-Head In The World Series

John Middleton of the Phillies and Jim Crean of the Astros made their fortunes in very different ways.


HOld Court Sunday at Citizens Bank Park after his Philadelphia Phillies earned a trip to the World Series, owner John Middleton honored superstar outfielder Bryce Harper, whose eighth home run was the margin of victory. “I think maybe I underpaid him,” said Middleton, who is paid $330 million over 13 years.

It’s not Harper that Middleton, 67, has to thank. This is Major League Baseball. In any other season, the Phillies would be watching the playoffs between tee times instead of chasing a third World Series title. But during this year’s collective bargaining talks, the league tried to expand the postseason, resulting in a 12-team field, up from eight the last time Philadelphia won the World Series in 2008. The change allowed the 2022 Phillies to sneak into the dance with a paltry 87 wins, the fewest of any playoff team this year. Compare that to the 106 regular-season wins of the Phillies’ World Series opponents, the Houston Astros, who are owned by fellow billionaire Jim Crane.

MLB postseason expansion comes down to money. According to industry insiders, ESPN has spent at least $65 million on additional playoff games under its existing television contract. Apple and Peacock’s new deal, worth $115 million a year, brings the total value of MLB’s media rights past the $2 billion mark.

With the promise of other new revenues, such as jersey patch sales and continued growth in sponsorship sales, there has never been a better time to own a baseball team. According to reports, MLB clubs are now worth an average of $2.07 billion, up 9% from last year. Forbes Estimates have both the Phillies ($2.3 billion) and Astros ($1.98 billion) eighth and 15th, respectively, based on team value in the first half of the league. Overall, MLB expects revenue to exceed $10 billion in the 2022 season.

“I think the higher the valuations, the more people are lining up to buy teams,” said Martin Conway, a professor at Georgetown University’s Institute of Sport Management. “It’s almost like art, regardless of what happens in the rest of the market, it just keeps going up in value.”

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That’s welcome news for the billionaire owners of both franchises, who have most of their wealth tied up in baseball. Middleton, who made his money by reviving and later selling his family’s tobacco business, is worth an estimated $3.4 billion. Crane is self-made and has turned his logistics business into a sports property, amassing a net worth of about $1.6 billion.


A billionaire will surely win

The value of MLB teams continues to increase, adding to the wealth of the owners of World Series contenders.


Philadelphia Phillies: John Middleton

Middleton’s wealth dates back to the 19th century. In 1856, his grandfather established a retail tobacco shop in Philadelphia. Almost 100 years later, the business began producing cigars, launching the popular Black & Mild cigar brand in 1980.

According to Middleton, he joined the family business the summer he turned 16 Philadelphia MagazineAnd after college at Amherst and a Harvard MBA, his father quickly promoted him to the company’s board (the other two members were his parents). Despite considerable opposition from his father, Middleton led the acquisition of four tobacco brands from RJ Reynolds, creating a profitable packaged cigarette business.

This opened the door for John and his father, both baseball enthusiasts, to join the Phillies ownership group in 1994. They acquired 15% of the club for $18 million and John made it a point to be active in the club’s operations.

After his father’s sudden death in 1998, Middleton consolidated ownership of the family business, buying out his mother and sisters for $200 million in 2003. Considering Middleton turned around and sold the business to Altria for $2.9 billion, it was quite the deal. 2007. His sister later sued him for more than $1 billion, claiming he misrepresented the company’s assets when she bought his shares. The siblings reportedly settled for $22 million in 2018 Philadelphia Inquirer.

Since exiting the tobacco business, Middleton has only increased his investment in the Phillies. He eventually increased his stake to 48% and took over the club after then chairman David Montgomery fell ill. MLB blessed him as the team’s official controlling partner in 2016. Today, Middleton co-owns the Phillies with the Buck family, investors who bought part of the team in 1981. Former Phillies general manager Pat Gillick and the Montgomery family, former team presidents, have smaller stakes.

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Houston Astros: Jim Crain

Crane, 68, took a different path to success. He grew up as a baseball-crazy kid in St. Louis, occasionally pitching to Cardinals players at local golf clubs and parking cars for patrons at the team’s stadium. He pitched for Central Missouri State University in the mid-1970s and still holds the school’s single-game hitting record with 18.

In 1984, after working in the insurance and shipping businesses, the 30-year-old Crane borrowed $10,000 from his sister and founded the company that became Eagle Global Logistics in Houston. Crane handled the details himself and the business made money in the first month. More than two decades later, in 2007, he sold the company in a leveraged buyout to Apollo Global Management, pocketing more than $300 million. A year later, Crane launched another logistics business, Crane Worldwide. Today, its annual gross income reaches 1.6 billion dollars.

It was around this time that Crane made his first attempt at MLB ownership. In a handshake deal, he agreed to buy the Astros in 2008, but he backed out, angering then-owner Drayton McLean Jr. and then-commissioner of baseball Bud Selig. New York Times. Crane went on to make unsuccessful plays for the Chicago Cubs and Texas Rangers.

His persistence was rewarded in 2011 when he struck a $680 million deal to buy the Astros and a minority stake in a newly created regional sports network. (His Astros contribution is estimated at about 40%). MLB has been investigating and personally naming Crane for months over an Equal Employment Opportunity Commission investigation that accused Eagle Global of racial and gender discrimination in the 1990s. (The company settled for $8.5 million, with $6 million later returned when an arbitrator determined that only 10% of the claims were valid.)

When Crane officially took over, the Astros were downright awful and had back-to-back 100-loss seasons. The club was widely criticized for losing out on collecting top picks in the draft, but if that was the team’s strategy, it paid off. Until 2014, the Astros had arguably the best farm system in baseball, producing stars like Alex Bergman, Carlos Correa and George Springer. The Crane regime also held off marquee deals, including the acquisition of future Hall of Famer Justin Verlander in 2017. That season, the club won its first World Series.

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The legendary turn ended in a nightmare. In 2019, Athletes It accused the Astros of using cameras and other technology to steal signs from opposing teams and give them unfair points. After interviewing 68 people, including 23 Astros players, and reviewing 76,000 emails, MLB found the cheating allegations to be true. The league suspended manager AJ Hinch and general manager Jeff Luhnow for one year, fined the Astros $5 million and stripped them of their 2020 and 2021 first- and second-round picks. Commissioner Rob Manfred exonerated the team owner, saying in a statement that Jim Crain was unaware of any MLB rule violations by his club. Crane fired Hinch and Luhnow.

“I think what the baseball world wanted him to say was a lot more apologetic than what he did,” Conway said. But on the other hand, the people of Houston seemed to see that as a positive, that he wasn’t going to back down and spend or do the other things that they were doing. “The city of Houston and the fans have gotten behind them and perhaps even more so because they’ve been shunned by almost everyone else in sports, baseball and the media.”

More information from Forbes

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