Both the Brewers and Phillies have had shorter-than-expected postseason runs as of late. Could a Devin deal bring them both closer to the World Series?

Why They Need Him

There isn’t a lot in common between Philadelphia and Milwaukee. Other than the phonetic parallels between “cheese” and “cheesesteak,” the main shared characteristic between the two cities is how their baseball teams have struggled to translate regular season success into meaningful playoff performances.

The Phillies have had back-to-back heartbreaks after making the World Series in 2022 as a Wild Card team.

In 2023, they seemed nigh untouchable at home but folded under the pressure of a seven-game Championship Series against the Diamondbacks.

In 2024, they won 95 games, the second-most in baseball, but once again lost to an underdog team that barely squeezed itself into the bracket, as the Mets needed just four games to end Red October before the Phillies even made it back to the NLCS.

The statistics reflect this lopsided success story. The team had a regular-season OPS of .750 (5th in MLB) and an ERA of 3.85 (11th in MLB).

The rotation was especially solid, led by Cy Young finalist Zack Wheeler, and strong seasons from Aaron Nola, Cristopher Sánchez, and Ranger Suárez, all of whom are still under team control in 2025. The bullpen picture was a little iffier, a problem that would rear its ugly head at the worst possible time.

Hoping to recapture the success he found in 2023, they redeployed José Alvarado as their closer to subpar results, eventually pivoting to Jeff Hoffman.

To his credit, Hoffman was pretty good, posting a 2.17 ERA and ten saves, but wanting a more experienced closer, the team acquired Carlos Estévez from the Angels at the deadline. With great backup options like Matt Strahm and even Orion Kerkering, it seemed like the bullpen was set, but the postseason figures told a different story.

Phillies relievers combined for a gruesome 11.37 ERA across 12 ⅔ innings during the NLDS. Hoffman (40.50 ERA, 1 ⅓ IP), Alvarado (27.00 ERA, ⅔ IP), and Strahm (18.00 IP, 2 IP) couldn’t get it together, and despite pitching admirably, Estévez blew a crucial save by giving up an epic grand slam to Francisco Lindor in the final game of the series.

Devin Williams doesn’t have the greatest postseason record, but with Estévez now a free agent, he could be the fix the team needs to have more pitching stability in later innings.

Hoffman’s past two years have been great, and Strahm has shown incredible promise, but Williams would be the only reliever with extensive experience as a closer, giving the bullpen a leg up.

What They Have to Offer

The Phillies have a decent group of prospects under control, topped off by four names in MLB’s Top 100 ranking. The type of player most closely aligns with Milwaukee’s typical trade haul would be prospects ready to make the big leagues within the next year or two.

Furthermore, with a strong nucleus of young position players in the lineup and farm system, they’ll likely hone in on pitchers with high developmental upside.

Andrew Painter and Mick Abel fit this description well but are likely too juicy for a rental reliever. Instead, an interesting alternative could be Jean Cabrera (#13 PHI prospect), a right-handed starter who posted a 3.39 ERA over 14 starts with High-A Jersey Shore. He jumped to Double-A Reading towards the end of the season and struggled to find the same success, but he’s just turning 23 and still has plenty of time to figure things out. Scouts note him as having a sinker in the mid-90s and a four-seamer up to 98 mph, two weapons that play well off of his changeup.

While likely insufficient by himself, right-handed reliever Wen-Hui Pan might also be worth a look. He posted a 1.29 ERA and 9.4 K/9 over 21 innings with High-A Jersey Shore. Scouts credit his high-velocity fastball that can touch 100 mph with a good arm-side run for his success and an outstanding splitter with very little spin. His inning count is low after missing time due to a broken pinkie he sustained in spring training, but that shouldn’t be a recurring issue.

Moisés Chace was a trade piece that sent Gregory Soto to the Orioles at this year’s deadline. After performing well in High-A, the Phillies promoted him to Double-A Reading, where he made four starts.

Over the 80 ⅓ innings he pitched this year, he had a 3.59 ERA and a wicked 13.9 K/9.

His fastball has a lower velocity than some, but with a great ride and low vertical approach angle, he makes it work in the upper part of the strike zone, akin to Paul Sewald. His unorthodox profile could be yet another fun project for the Brewers’ pitching lab to perfect.

Outside of pitchers, the Phillies don’t have a lot to offer that would feasibly make the Brewers better.

Milwaukee could ask for someone like Otto Kemp, an infielder with solid numbers in Single-A and Double-A, to use in a future trade to acquire someone else, but the pickings are slim otherwise.

So what’ll it be for the Phillies: another awesome regular season followed by a bullpen collapse at the eleventh hour or a fresh closer ready to save the city from its rabid fans?

With so much talent already on the team and just one primary area of weakness, adding Devin Williams could be like sealing up that one gap in the Death Star and making this roster impregnable.