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

John Middleton of the Phillies and Jim Crain of the Astros built their fortunes in different ways.

HOwner John Middleton thanked superstar shortstop Bryce Harper, whose eighth-inning home run was the margin of victory Sunday at Citizens Bank Park after his Philadelphia Phillies advanced to the World Series. “I think maybe I underpaid him,” said Middleton, who is paying the forward $330 million over 13 years.

It’s not Harper that Middleton, 67, should be grateful for; this is Major League Baseball. In any other season, the Phillies would have been in the playoffs instead of winning a third World Series title. But during collective bargaining this year, the league pushed for an expanded season, and the result was a 12-team field, up from eight teams since Philadelphia last won the World Series in 2008. This change allowed the 2022 Phillies to sneak in. to dance with 87 wins, the fewest of any playoff team this year. Compare that to the 106 regular-season wins of the Houston Astros, the World Series rivals of the Phillies, owned by billionaire Jim Crane.

MLB postseason expansion is all about money. According to industry insiders, ESPN has committed at least $65 million to additional playoff games under its existing television deal. The new deals from Apple and Peacock, worth $115 million annually, bring the total value of MLB’s media rights past $2 billion.

With the promise of other new revenue streams such as jersey patch deals and the continued growth of sponsorship sales, there has never been a better time to own a baseball team. MLB clubs now average a record $2.07 billion, up 9% from last year. Forbes assumptions. Both the Phillies ($2.3 billion) and Astros ($1.98 billion) are in the upper half of the league in terms of team value, ranked eighth and 15th, respectively. Overall, MLB expects revenue to exceed $10 billion in the 2022 season.

“It seems to me that the higher the prices, the more people will line up at the door,” says Martin Conway, a professor at Georgetown University’s Institute of Sport Management. “It’s almost like art, no matter what happens in the market, it continues to increase in value.”

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That’s good news for the billionaire owners of both franchises, who have tied up much of their fortune in baseball. Middleton, who made his money from reviving and then selling his family’s tobacco business, is worth an estimated $3.4 billion. Crane is a self-made man who turned his logistics business into a sports property and has amassed a net worth of about $1.6 billion.


MLB teams continue to increase in value, adding to the wealth of World Series contender owners.

Philadelphia Phillies: John Middleton

Middleton’s wealth dates back to the 19th century. In 1856, his great-grandfather founded a small tobacco shop in Philadelphia. About 100 years later, the business began producing cigars, and in 1980 it launched the popular Black & Mild cigar brand.

According to Middleton, he joined the family business the summer he was 16 Philadelphia Magazine, and after college at Amherst and an MBA at Harvard, his father quickly brought him onto the company’s board (the other two members were his parents). Despite considerable encouragement from his father, Middleton led the purchase of four tobacco brands from RJ Reynolds and built a profitable cigar packaging business.

This opened the door for John and his father, who were both into baseball, to join the Phillies ownership group in 1994. They collected 15% of the club for $18 million and John indicated that they would be active in the club’s activities.

After his father died suddenly in 1998, Middleton consolidated ownership of the family business and bought out his mother and sisters in 2003 for $200 million. 2007. His sister later sued him for more than $1 billion, claiming he misrepresented the company’s assets when he bought the stock. According to the publication, the brothers settled for 22 million dollars in 2018 Philadelphia Inquirer.

After leaving the tobacco business, Middleton only increased his investment in Filius. 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 managing partner in 2016. Today, Middleton owns the Phillies along with the Buck family, investors who bought a piece of the team in 1981. Former Phillies general manager Pat Gillick and the Montgomery family, former team chairman, own smaller shares.

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Houston Astros: Jim Crain

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

In 1984, after working in insurance and freight forwarding businesses, the 30-year-old Crane borrowed $10,000 from his sister and founded what would become 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 to Apollo Global Management in a leveraged buyout, pocketing more than $300 million. A year later, Crane started another logistics business called Crane Worldwide. It has annual revenue of about $1.6 billion today.

It was around this time that Crane made his first foray into MLB ownership. In a handshake deal, he agreed to buy the Astros in 2008, but he agreed, angering then-owner Drayton McLain and then-commissioner of baseball Bud Selig. New York Times. Crain continues his streak of no-hitters for Chicago Cubs and Texas Rangers games.

His persistence was rewarded when in 2011 he secured a $680 million deal to buy the Astros and a minority stake in a newly formed regional sports network. (His stake in the Astros is about 40%.) Crain also received a $70 million discount on the deal by agreeing to the club’s move to the American League. MLB has been investigating Crane for months since the Equal Employment Opportunity Commission, which accused Eagle Global of racial and sex discrimination in the 1990s, named him personally. (The company settled for $8.5 million and was later refunded $6 million when an arbitrator found only 10% of the claim valid.)

When Crane officially took over, the Astros were extremely bad, posting over 100 losses in back-to-back seasons. The club has been widely criticized for losing out on collecting top draft picks, but if that was the team’s strategy, it paid off. By 2014, the Astros were arguably the best farm system in baseball, producing stars like Alex Bregman, Carlos Correa and George Springer. Crane’s regime also pulled off marquee trades, 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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A fantastic comeback ended in horror. In 2019, Athletic Accused the Astros of using cameras and other technology to steal signs from opposing teams, giving them an unfair advantage. After interviewing 68 people, including 23 Astros players, and examining 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 forfeited their first and second draft picks in 2020 and 2021. Commissioner Rob Manfred released the owner, saying in a statement that “Jim Crane was unaware of any violation of MLB rules by his club.” Crane fired Hinch and Lukhnov.

“I think what the baseball world wanted him to say was more apologetic than he really was,” Conway says. “But on the other hand, people in Houston seemed like it was a positive that he didn’t want to back down and stop spending or doing the other things that they were doing. The city of Houston and the fans are behind them. received and perhaps even more rallied around them because they felt alienated by everyone else in sports, baseball, and the media.”


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