Aug 16, 2024; Philadelphia, Pennsylvania, USA; Philadelphia Phillies owner John Middleton before a game against the Washington Nationals at Citizens Bank Park. Mandatory Credit: Bill Streicher-USA TODAY Sports Bill Streicher
Former Montreal Expos and Miami Marlins executive David Samson had some interesting thoughts about the Phillies on a recent episode of his "Nothing Personal" show.
While I don't know David personally, I like listening to his show. I don't always (or usually) agree with him. But I think he represents the cold, calculating business man who has power not only in baseball organizations, but many companies. And he owns it. So even if he comes off as unrelatable most of the time, you know that he's speaking for a lot of people in positions of power in corporate America.
A clip posted to Samson's YouTube page Tuesday was entitled "The Philadelphia Phillies have ONE LAST SHOT at a ring with this roster!" That may be true given the ages of many of the key pieces on the roster, but Samson's point wasn't really to say that time is running out to win with the core of Bryce Harper, Zack Wheeler, Trea Turner and Kyle Schwarber. His point was that managing partner John Middleton and his ownership group can't afford to continue spending how they have for nearly half a decade now:
"The Phillies this year have a projected payroll of $317 million. And this year will be the fifth year in a row that the club has gone into luxury tax territory. Five years. It'll be the second year in a row that they've cleared the highest threshold. What has their return on their investment been exactly? What is it that makes them continue to have the depth that they have, but not have the results that they want or need? If I knew that I was running a club that was constantly over the tax threshold, I would be asking the owner whether he is of sound mind or not. The punitive nature of being over the apron is so significant, the juice is not nearly worth the squeeze."
The Phillies were one of nine teams to pay the luxury tax in 2025. According to The Associated Press, only the Los Angeles Dodgers, New York Mets and New York Yankees paid higher luxury tax penalties than the Phillies, who paid $56.1 million.
Additionally, the Phillies will pay a 110% tax on all payroll above $304 million this year, which is a significant penalty. Phillies fans may wish the payroll was even higher, but this ownership group has been one of the most aggressive in the league in recent years. It's entirely possible that from a bottom line sense — even with sellout crowds and one of the few remaining strong local TV deals — the Phillies have lost money in some or all of the last few seasons.
But it's laughable to suggest the Phillies haven't gotten a strong return on their investment over the last four years. No, they haven't won a World Series. But after a decade out of the playoffs, they've brought back pride around the city's baseball team with four consecutive postseason trips and a World Series berth in 2022. The idea that none of that matters is, to use a phrase from Harper, wild.
Samson continued:
"What I keep wondering about ... when you are John Middleton, and you have wanted nothing more than to win a World Series, and you haven't won one in your tenure, period, hard stop ... what do you do? What do you do when you know your spending is not sustainable? In your own life, what do you do? When your expenses are so much that you're buying stuff on Amazon, or you're doing whatever it is you're doing. What do you do eventually? Don't you eventually just stop, because you run out of money? To me, it is incredibly unlikely that the Phillies continue this streak of being above the tax threshold. This is the last season that these Phillies will continue to be together, and 'run it back for the most part,' as they attempt to get to and win the World Series. The Phillies are going to have to lower their payroll, and put it in line with revenues."
First of all, it's just not true that Middleton hasn't won a World Series in his tenure. The Phillies haven't won the World Series since he succeeded David Montgomery as the face of the ownership group in the mid-2010s, but he was part of what Richard Rys of Philly Mag dubbed "The Phantom Five" in May of 2008, a largely silent ownership group. When the Phillies won the World Series that fall, Middleton was definitely there. When the Phillies lost to the Yankees in the 2009 World Series, Middleton famously told Ryan Howard "Ryan, I want my fucking trophy back. It’s fucking ours."
Secondly, comparing how you run your household budget with the operations of a professional sports team is foolish. Comparing the finances of an every day person to a billionaire is tone deaf. It also ignores that Middleton — who is estimated by Forbes to be worth $4.3 billion — doesn't even own half the team. The Phillies don't reveal specific percentages of their ownership group, but Middleton owns less than 50% of the team. The Phillies added three new limited partners in November of 2024, just over a year after Stanley Middleman bought at 16.25% stake in the team.
At the time of the new trio being added, MLB.com's Todd Zolecki wrote that "when the Buck family decided to divest a couple of years ago, Middleton made it clear to prospective investors that he prizes winning above everything, so anyone who joined would need to be on board with that philosophy."
So all these new owners knew what they were signing up for. And there's enough money in this group that it's comical to suggest that the Phillies are in danger of running out of money in the same way that you would be if you bought a few too many items in an online shopping spree.
Again, that's not to say that this has been the most profitable time for the ownership group, because it probably hasn't been. But the real divide that no one wants to talk about ahead of what's sure to be a prolonged labor battle next offseason is between owners who manage their teams like a business (as Samson is advocating for), and ones who are independently wealthy and feel that they have a responsibility to the public to win it all, even if it means the clubs (which are still growing in value) run a deficit on a year-to-year basis.
Fortunately for Phillies fans, Middleton appears to be in the latter group. That shouldn't be taken for granted, because it's unclear if that will continue when the 70-year-old is no longer at the forefront of the ownership group. You can look at the Detroit Tigers, Washington Nationals and San Diego Padres as evidence that the kids aren't always invested as the parents were. Will the Phillies be running a top-five payroll every season in 50 years? Who knows.
But this was a club that just offered Bo Bichette a seven-year deal in the range of $200 million this offseason. They do have some significant money set to come off the books next winter just from Nick Castellanos ($20 million) and Taijuan Walker ($18 million). If some or all of Justin Crawford, Andrew Painter and Aidan Miller are legit, they will be cheap for a few seasons. Perhaps the Phillies payroll in 2027, assuming there is a season, won't be quite as high as 2026 because of those factors.
However, there's just not any evidence that the Phillies plan or need to cut payroll massively after this year. If anything, recent evidence suggests they will continue to pour money into the club in pursuit of on-field greatness.
