When catcher J.T. Realmuto joined the Philadelphia Phillies in February 2019, the organization was top-notch in almost every respect—except for one detail.
“I wouldn’t say I requested a new plane,” Realmuto remarks. “But I did point out that there were better options available.”
For instance, the Miami Marlins, who traded Realmuto, flew on a Delta Boeing 757 equipped with custom card tables and additional first-class seating. In contrast, the Phillies were using a standard United jet. So, when Realmuto signed a five-year, $115.5 million contract with the Phillies in 2021, he casually brought up the plane situation to president of baseball operations Dave Dombrowski. Dombrowski then spoke to team owner John Middleton, and by the next season, the Phillies were flying on the same type of plane as Miami.
What did this change cost?
Middleton, who was taking a break during batting practice to hand out balls to fans, shrugged it off. “I really don’t care,” he said. “What matters to me is that the players aren’t thinking, ‘Wow, look at these cheap guys.’”
No one would accuse Middleton of being tight-fisted. This season, the Phillies have the fourth-highest payroll in Major League Baseball at $242 million, marking the fifth consecutive year they’ve ranked in the top 10. Players and staff members credit Middleton as one of the best owners in the game, recognizing his commitment to spending on more than just player salaries, which has contributed to the team’s success as they pursue a third consecutive deep playoff run.
“This isn’t just a job or an investment for him,” says right fielder Nick Castellanos. “He genuinely wants to win. He’s not Santa Claus, but he uses good judgment. If our requests are reasonable, he usually makes it happen.”
As major league teams face restrictions on financial advantages regarding player salaries, Middleton—who is 69 and the heir to a tobacco fortune—has redirected funds toward off-field improvements.
“When I signed here, that was a significant factor,” says first baseman Bryce Harper. “Anything that can help the team succeed—training staff, food, clubhouse amenities, travel—he understands what we need, not just for players, but for the staff too. He’s dedicated to delivering the best.”
When Harper’s wife, Kayla, showed an interest in nutrition, he asked team chefs to source pasture-raised beef and raw milk from Amish country. Upgrades quickly followed when players voiced concerns about outdated batting cages and requested a new pitching machine. When designated hitter Kyle Schwarber expressed a craving for hibachi, the team had it ready after their game in Pittsburgh.
Middleton, who maintains close relationships with former players like Carlos Ruiz, often supports improvements without needing to consult higher-ups. Dombrowski noted that changes for the players typically don’t require Middleton’s explicit approval because he already knows Middleton’s supportive mindset.
“I’ve told Dave since he got here: ‘Your job is to create a championship team, and mine is to provide the resources to make that happen,’” Middleton explains. “That championship team involves more than just the players. If they see new batting cages, red jerseys, or a nicer plane, it creates a positive atmosphere. Happy players can focus on winning, not on complaints about cheap amenities.”
Middleton has embraced a management philosophy he calls “management by wandering around,” inspired by the book *In Search of Excellence*. He believes in being present, interacting with employees and players rather than remaining hidden in an office.
He chuckles when asked if picking up balls after batting practice fits into this philosophy. “Absolutely,” he says. “That concept made a lasting impression on me, and I’ve practiced it throughout my career.”
He values personal interactions and relationships, especially when evaluating potential star acquisitions. He emphasizes the importance of understanding a player’s character and how they fit within the clubhouse culture. To have these candid discussions, he believes a foundation of trust is essential.
Although he initially worried about overstepping his baseball operations staff, he has learned to know when to step back and heed their advice. For instance, when players requested to change the annual family trip date, he consulted Dombrowski and agreed to maintain the original timing to avoid distractions.
“I must support that overall effort,” he says. “You want a good manager and general manager working cohesively, without an owner constantly saying no.”
To foster goodwill, Middleton often says yes. For the alumni weekend, he personally covers costs to host former Phillies and their families at his home, believing it’s vital for them to feel appreciated.
After the Phillies won the National League pennant in 2022, he provided high-quality rings to everyone in the organization, including replicas for players to gift to loved ones.
“Sure, we could have saved money by opting for less extravagant rings,” he admits. “But investing in our culture is essential. Ultimately, our legacy will be judged by our success on the field. If spending money helps attract players and makes them happier, that’s worth it.”
He reflects on baseball’s history, citing legendary teams like the 1927 Yankees. “Did they turn a profit? Maybe. But who cares? No one is concerned about whether I make money.”
Including himself.
He shrugs. “My great-great-grandchildren might be upset with me, but I won’t know them!”
Leave a Reply