Jun 13, 2025; Boston, Massachusetts, USA; Boston Red Sox pitcher Garrett Crochet (35) throws a pitch against the New York Yankees in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images David Butler II
Phillies' managing partner John Middleton met with the media Friday, and while the countdown to the 2026 MLB All-Star Game at Citizens Bank Park was the primary topic, there was some discussion of the upcoming July 31 trade deadline.
When the Phillies reassigned former general manager Matt Klentak in October of 2020, Middleton spoke of a desire for the organization to get better at developing talent, something they had rarely done well in the long history of the franchise.
Fast forward close to a half decade, and the Phillies are in a much better situation with their farm system. But they're also at the back half of a World Series window. So how, in Middleton's estimation, will president of baseball operations Dave Dombrowski balance wanting to make the most of this core without gutting a farm system that's turned around in a pretty drastic way in recent years?
"Well, I agree with Dave," Middleton said. "Some of those players are in the back half of their careers for that window. But there are other players who are at the beginning of their window. You gotta keep thinking about that."
It is true that a franchise with the financial might that the Phillies possess shouldn't fall off a cliff when a current core ages out, like they did from 2012-2017.
But it's also true that the Phillies aren't going to have the chance to sign Hall of Fame-level performers like Bryce Harper, Zack Wheeler and Kyle Schwarber at the peaks of their power in every era. And if you're a good team that's spending a lot of money, it's more difficult to find superstars in the MLB Draft.
👂🎧 John Middleton gave @TimKellySports a very candid answer when discussing balancing wanting to keep prospects with trying to maximize this World Series window. pic.twitter.com/x6BzKojui7
Middleton, though, made an astute point in reflecting on how the Phillies operated from 2009-2011, when they tried to add a second World Series trophy to that era after winning it all in 2008.
Ruben Amaro Jr. — who was promoted to general manager when Pat Gillick retired after 2008 — acquired Cliff Lee (x2), Pedro Martinez, Roy Halladay, Roy Oswalt and Hunter Pence between 2009 and 2011. It produced a lot of regular-season wins, but didn't put another ring on the fingers of Middleton and key contributors from that era.
"Every move that he made was an A+ move," Middleton said. "Every player that he brought in performed at a very high level. And we still lost. Not only did we not win the World Series, but we exited every year one round earlier than the year before.
"You can do everything right and you still don't win. It's a bad call ... it's a bad break ... a bad bounce of a ball ... it's some guy just gets ridiculously hot and beats you," Middleton added. "So those things, you have to weigh all that because we're gonna be playing baseball in five or 10 years from now, right? And we want the fans to be excited about the team 5 or 10 years from now. And to do that, you can't just trade everybody."
It's clear that the scars of 10 straight seasons without a playoff appearance after the golden era of 2007-2011 continue to be part of the calculation for the Phillies. And they probably should be. As he points out, games in 2030 will count just as much as ones in 2025.
John Middleton: “A bullpen in the regular season is an entirely different animal than a bullpen in the postseason.”
(Via @TimKellySports) pic.twitter.com/aRgs9DLsrX
Middleton, without naming any names, added that there are also names that Phillies fans would probably like to see the team acquire aren't actually available. Also, there are ones who will come with too steep of an asking price for the Phillies to meet.
The Phillies, according to Middleton, had a particularly difficult time balancing the present with the future last summer when they were trying to acquire LHP Garrett Crochet from the Chicago White Sox.
"We made a spectacularly good offer," Middleton revealed. "So good that Dave looked at me at one point and said, 'I don't know that I should be doing this.' And he said, 'You know what, I'm ambivalent. If they take the deal, great. If they don't take the deal, great. I'm really happy with keeping the guys we were gonna give them.' And that's the way I was."
ESPN's Buster Olney and Jesse Rodgers reported that the Phillies weren't willing to part with No. 1 prospect Andrew Painter in talks for Crochet. Matt Gelb of The Athletic later reported that the Phillies offered the White Sox a package of prospects that included Aidan Miller and Justin Crawford, only for Chicago to turn it down. When the White Sox circled back in the offseason, not only did the Phillies continue to keep Painter off the table, but Gelb reported that they weren't willing to replicate the offer from the summer.
Crochet was ultimately dealt to the Boston Red Sox. In his first season with the Red Sox, Crochet has been one of the best pitchers in baseball, as he'll enter the second half leading the sport with 160 strikeouts and 129 1/3 innings pitched. He is tops in the AL with a 2.23 ERA and 185 ERA+. As is, the Phillies' rotation is probably the best in baseball, even if Jesús Luzardo has been hit-or-miss since a scalding-hot start. But if you swapped out Luzardo for Crochet, the Phillies might have baseball's best rotation since their 2011 one that included Roy Halladay, Cliff Lee, Cole Hamels and Roy Oswalt.
To Middleton's point, though, despite winning a franchise-record 102 games in 2011, the Phillies went home in the NLDS. The 1990s Braves only won one title with perhaps the greatest starting rotation in MLB history. Manny Ramirez (Los Angeles Dodgers) and CC Sabathia (Milwaukee Brewers) were two of the best trade deadline pickups ever, yet both of their clubs were eliminated in the playoffs in 2008 by the Phillies, who opted for more modest additions like Joe Blanton.
There's the desire to take a big swing before every trade deadline. That's heightened this year for the Phillies, both because of a clear need for a bullpen makeover and the finite amount of years with this current core. But making a major move wouldn't assure a parade in late October, and as the Mets are now finding out as Pete Crow-Armstrong has developed into a superstar with the Chicago Cubs, sometimes the short-term reward (a couple months of Javier Báez, in that case) isn't worth the long-term consequences.
"You have to balance that," Middleton said. "He's got 40 years in the business. Nobody is perfect, nobody gets every call right. But he's made a lot of them really well. And so, you just have to trust Dave to think this through."
