The Phillies’ win-now window: What the Zack Wheeler extension means for 2025 — and beyond


As Zack Wheeler sat Monday morning in a cafeteria wearing a rumpled plain T-shirt, extolling the virtues of an organization that keeps throwing big money at star players, it had been 717 days since the Phillies crossed the Rubicon. The defining moment of this free-spending era was not Bryce Harper’s $330 million, or Wheeler’s initial $118 million contract, or another $300 million handed to Trea Turner.

It was March 18, 2022, when Nick Castellanos agreed to a $100 million contract — and pushed the Phillies above the threshold that triggered the luxury tax for the first time ever. For years, the Phillies had danced around it. Team officials insisted it was not a hard cap but often treated it as such.

But the Phillies had hired Dave Dombrowski to guide them from the rebuild darkness and, ever since, Dombrowski has excelled at what he does best — convincing rich owners to spend more of their money.

Once the Phillies waded into the tax penalties, they started to win, and the whole thing is intoxicating. It’s why Wheeler did not have to entertain free agency; the Phillies agreed to pay him the fourth-highest annual salary in baseball history with a three-year, $126 million contract extension that begins in 2025. The Phillies are now known throughout the industry as an organization that takes care of its players — on and off the field.

There is no more dawdling. The Phillies know what they want, and they are not concerned with the efficiency of it all. It is not a long-term business strategy, but it is the one the Phillies have chosen in the immediate. They have already committed $207.4 million in payroll (as calculated for luxury-tax purposes) to nine players for 2025. That is the highest figure in baseball and $20 million more than the Dodgers.

The future?

“Figure let’s tackle that at the end of the year, and we’ll see where it takes us,” Dombrowski, the club’s president of baseball operations, said at Monday’s news conference. “But, sure, there’ll be some challenges.”

This is how the Phillies do business now. Consider how the negotiations with Wheeler’s agent, B.B. Abbott of Wasserman, began: “Well,” Dombrowski remembered telling him, “let’s establish right now he’s one of the best pitchers in baseball. Is he first, second, third? We don’t have to get into that. But he’s one of the best.”

The minutiae should not derail a good transaction. There is no need to debate Wheeler’s exact place in baseball. Maybe it means spending a few extra million here or $10 million there. So be it.

“Zack really wanted to pitch here,” Phillies managing partner John Middleton told reporters in Clearwater, Fla. “We obviously really wanted him to pitch here. You find a way — you just have to kind of get it done.”

Between Wheeler and Aaron Nola, the Phillies have spent $298 million in the past four months on starting pitchers in their 30s. That is not typically advisable. There are risks, and the Phillies have acknowledged as much. Quality starting pitching is expensive. Developing it is difficult. Winning without it is almost impossible.

So, 717 days after the Phillies crossed into uncharted territory, they minted their first $40 million-plus player. There are future ramifications; the Phillies have contemplated them even if Dombrowski did not want to elaborate on Monday. The goal is to compete for a championship now while avoiding a complete cratering of the franchise similar to the one that unfolded in 2012-14 and bled into the unmentionable years. The Phillies have a win-now window, but it’s not absurd to thread the needle with much of this current group and an infusion of younger talent in 2026 and 2027.

Wheeler even broached the subject as the Phillies negotiated his massive deal.

“That was something that we talked about,” Abbott said. “I talked a lot about that with Dave, who in turn talked about that with Mr. Middleton. And they seem confident they can take this window — we were calling it a championship window — and put a really good team around him and on the field.”


Zack Wheeler’s extension will push the Phillies payroll to new heights in 2025. (Eric Hartline / USA Today)

The Phillies will field a massive payroll in 2025, once Wheeler’s extension begins. They will certainly exceed the second tax threshold — triggering stiffer financial penalties — and will have a difficult time avoiding a payroll that climbs above $281 million. That’s the third threshold in 2025, and if the Phillies eclipse it, their top selection in the 2026 MLB Draft will be moved back 10 places in the order.

It’s not ideal, but it is not a back-breaking punishment — especially if the Phillies are picking near the end of the first round, as they hope. This is one reason they have worked hard to retain their full allotment of picks for the 2024 draft; the Phillies did not sign a free agent attached to a qualifying offer for the first time in years. Those missing picks — and the bonus money that comes with them — have harmed their farm system. (This is but one reason the Phillies have never seriously discussed Blake Snell, multiple major-league sources said — no matter how short the deal is.)

Their only free agents after 2024 are Matt Strahm, Seranthony Domínguez and Whit Merrifield. The Phillies hold club options on Domínguez and Merrifield. J.T. Realmuto and Kyle Schwarber are free agents after the 2025 season. So is Ranger Suárez. Nick Castellanos, Taijuan Walker and Alec Bohm are free agents after the 2026 season. That’s real money coming off the books, but also real needs that will have to be filled.

The Phillies’ farm system ranks in the bottom half of baseball, according to most evaluations. It lacks upper-level talent. But, given the current needs of the big-league club, those on the development side have time. The Phillies have invested in more high-ceiling hitting talent, and many of those prospects need two or three more years of experience. At least. Squint a little and it’s not hard to see how the Phillies are trying to align things.

With $207.4 million tied to nine players in 2025, there are certain roster realities.

“It means you’ve got to have some really good youngsters coming up, frankly,” Middleton said. “You need people like (Bryson) Stott and Bohm. You need (Johan) Rojas to develop, and you need (Brandon) Marsh to continue to develop. You need (Mick) Abel and (Andrew) Painter and (Griff) McGarry to develop and (Cristopher) Sánchez to develop. You need that. Because that’s kind of the blend that you have to have to be really successful in baseball, in my experience.”

Even so, with Middleton and Dombrowski atop the organization’s masthead, it will always be connected to star players. The Phillies drew three million fans in 2023 for the first time in a decade. Stan Middleman bought 16.5 percent of the club last summer and team sources have described him as an invested owner who is in line with Middleton’s philosophies on payroll expenditures. (Middleman has a title — vice chairman — and that separates him from other recent ownership partners who were not as involved.) The Phillies can keep spending on stars, but there will be a limit.

Maybe.

“I think we can find a way to do it if it becomes a necessity,” Middleton said. “But maybe the star that we add is Painter or Abel, or Rojas gets all of a sudden comfortable at the plate and he’s starting to hit .285 to .300 with his defense and he’s a star. And Marsh could be a star. Stott, I think, already is a star. … That’s what you need.”

All of that sounds great, but the Phillies know it never happens as planned. The Wheeler deal was a steep price to pay, but also sensible business. It’s what invested franchises do.

Now, they have to win.

“There is pressure to live up to the contract,” Wheeler said. “But if you take care of what you need to, hopefully, it will take care of itself on the field in the performance.”

The Athletic’s Jayson Stark contributed to this report. 

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(Top photo of Zack Wheeler receiving his 2022 National League championship ring from John Middleton and Dave Dombrowski: Gregory Fisher / Icon Sportswire via Getty Images)





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