Inspired by the Eagles’ Super Bowl win, John Middleton readies for another Phillies season with high expectations

Philly connects with its sports franchises differently than almost any other city. And when Middleton steps into the clubhouse Monday to address the Phillies, he plans to remind them.

Phillies owner John Middleton juggles baseballs during spring training last season in Clearwater, Fla.Read moreHeather Khalifa / Staff Photographer

by Scott Lauber

Published Feb. 14, 2025, 6:00 a.m. ET

CLEARWATER, Fla. — A week later, John Middleton is still processing it.

Middleton owns his hometown baseball team, a privilege he doesn’t take lightly, judging by how much money he spends annually to field a World Series contender. Foremost, though, he identifies as a Philadelphia sports devotee. And since he left Eagles owner Jeffrey Lurie’s suite and walked out onto the streets of New Orleans last Sunday night, he has tried to contextualize the Birds’ domination amid nearly seven decades of fandom.

“That Super Bowl was clearly one of the greatest sports moments in my life,” Middleton, 69, said Thursday in a wide-ranging interview from his third-floor office at the Phillies’ spring training complex. “I don’t know exactly where it would fall, but you’ve got the ’08 World Series and, frankly, the ’22 NLCS. They are the three. I’m not sure of the exact order.

“If I really had to think about it, I’d probably put the ’08 World Series as No. 1 because it was my team. I won as a fan, but I also won as an owner, and that was hugely significant for me. But I might well put the Super Bowl No. 2. It certainly wouldn’t be No. 3. Those two others [with the 2022 NLCS] might be tied for two. That’s how big it was.

“As a fan, I mean, you just can’t help but get charged up over the game but also over the fans’ reaction to the game — before the game, during the game, after the game. It was a spectacular experience. And so you carry that with you. It shapes you. It shapes your experience. It shapes your memories.”

It isn’t a uniquely Philly feeling, but surely Philly connects with its sports franchises differently than almost any other city. If you know, you know. And when Middleton steps into the middle of the clubhouse Monday to address the Phillies before the first full-squad workout, he will make sure that everyone — players, coaches, staff — knows. Or better yet, remembers.

Many got a taste in 2022, when the Phillies went on an unexpected ride to Game 6 of the World Series. But despite winning more games in each of the last two regular seasons and the organization’s first division title since 2011 last year, they backslid in back-to-back Octobers.

It didn’t sit well with Middleton, a former collegiate wrestler who joked that he tends to “get a little excited” when he watches his teams, regardless of whether he has invested more than $300 million in payroll (Phillies) or merely his heart and soul (Eagles).

After signing at least one player, often more than one, to a nine-figure contract in every offseason since 2018-19, the Phillies were quiet, relative to other NL contenders. The Mets dropped $765 million on Juan Soto; the Diamondbacks landed Corbin Burnes for $210 million; the Dodgers won the winter (after winning the World Series), adding a two-time Cy Young winner (Blake Snell), two All-Star closers (Tanner Scott and Kirby Yates), and a phenom from Japan (Roki Sasaki).

But for fans who feel angst over keeping the core intact for one more run at an elusive championship, Middleton remembers a time, a half-century ago, when the Phillies were vanquished in three consecutive League Championship Series, then missed the playoffs before coming back to win the World Series in 1980.

“Philadelphia has seen this play before,” said Middleton, who taps into his fan sensibilities by mingling with paying customers on the concourse at Citizens Bank Park and throwing baseballs into the stands from atop the dugout before playoff games. “I think people need to recognize that it is a really good team. We have a really good team. And frankly, we’re a better team today than we were when we walked out of Citi Field last October.”

Middleton’s basis for that statement: a solid starting rotation that got deeper with a December trade for lefty Jesús Luzardo and the looming return of top prospect Andrew Painter, who missed two seasons with a torn elbow ligament that necessitated Tommy John surgery.

“If Andrew Painter had been pitching for us for those two seasons before he hurt his arm, we might have won the World Series and won it more than once,” said Middleton, who recalled when Clayton Kershaw came out of the bullpen for the Dodgers against the Phillies as a 20-year-old rookie in the 2008 National League Championship Series. “Having Andrew Painter even coming out of the bullpen in ’23 or ’24 would have changed games, frankly.”

Maybe. But in 2025, the Phillies’ road to finally getting over the World Series hump might well be paved in a shade of green that not even the Eagles can inspire.

The Dodgers’ luxury-tax payroll stands at $392.5 million, according to Spotrac. After re-signing slugger Pete Alonso last week, the Mets are up to $321.5 million. Middleton has taken the Phillies’ payroll to unprecedented heights — roughly $306.2 million by some estimates — but it’s worth wondering how much higher he can go.

Having already surpassed the outermost luxury-tax threshold, a status that carries a 110% surcharge on every dollar over $301 million, is there a limit to how much more they can spend?

“I would say no,” Middleton said. “I look at the payroll — and I push [president of baseball operations] Dave [Dombrowski] to look at the payroll — as a meaningful guidepost. But that’s kind of all it is.”

So, if Dombrowski recommends that the Phillies would benefit from adding, say, another late-inning reliever or righty-hitting corner outfielder at the trade deadline in July, Middleton said he will authorize a move. The same goes for dealing from a stable of prospects in a rebuilt farm system the Phillies have fiercely protected over the last few years.

But Middleton also has charged Dombrowski to “win now and win later,” which explains why the Phillies didn’t pull off a prospect-rich swap for then-White Sox lefty Garrett Crochet at last summer’s trade deadline or this winter. Middleton conceded that they had “great opportunities” last July but “weren’t willing to pay the price that people were asking for us.”

It’s a delicate tap dance.

“I don’t think we get to the World Series without [trading for] Cliff Lee in ’09. I just don’t,” Middleton said. “And I would say the same thing about Roy Halladay. I don’t think we get to the NLCS [in 2010] without Roy Halladay. Those guys were real difference-makers. And if you can get them, as we got Roy, where you’re trading good players but you’re also getting an extension so it’s more than a rental, that’s significant.

“If Cliff or Roy’s equal is available in July, or would have been available this past December, I think you have Dave Dombrowski talking to me in a very different way than he was talking to me.”

But as Middleton quickly noted, two things can also be true.

”You can make those deals and sign Cliff Lee, trade for Cliff Lee, or trade for Roy, and you still don’t win,” he said. “So it’s hard.”

For now, then, Middleton will take his chances with the team he has. That includes a seven-player core — Bryce Harper, Trea Turner, Zack Wheeler, Aaron Nola, J.T. Realmuto, Kyle Schwarber, and Nick Castellanos — that makes a combined $182 million; a supporting cast that must keep improving (Alec Bohm, Bryson Stott, Brandon Marsh, Ranger Suárez, Cristopher Sánchez, Orion Kerkering); and a group of newcomers who are seeking to bounce back from injuries (Luzardo, Max Kepler, and Jordan Romano).

Middleton declined to share the message he’ll deliver when they gather together Monday morning. He typically comes up with a theme for his spring training speeches. Last year’s centered on wanting to win back his [dang] World Series trophy. It was a powerful sentiment. As Stott put it, Middleton was “the most fired up I think I’ve ever seen him.”

If those players were with him in Lurie’s suite last Sunday night, they might have seen him top it.

Call it a hunch, then, but Middleton probably will mention the Eagles and his powerful Super Bowl experience a time — or two.

“You can’t go through that last weekend and not [talk about it],” he said. “Most of these people, the players and staff, were on the ’22 team. They understand what Philadelphia’s like when you have a really good team and particularly when a really good team has a deep postseason run. Are there a few players who weren’t on that team who probably never experienced anything close to what we have in Philadelphia? But most of those guys were there and experienced it.

“To me, it’s more about trying to convey to them how extraordinary it was Sunday and get them remembering how extraordinary ’22 was and the feeling of winning the NLCS and going to the World Series. Just help them to remember more vividly what they went through and understand.”