3 sneaky trades Phillies must make to boost World Series chances

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3 sneaky trades Phillies must make to boost World Series chances

Zachary Howell · ClutchPoints

Sat, Jun 28, 2025 ·

4 min read

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The post 3 sneaky trades Phillies must make to boost World Series chances appeared first on ClutchPoints .

The Philadelphia Phillies have been neck-and-neck with the New York Mets for the division lead all season. Philadelphia manager Rob Thomson has dealt with drama amongst his players extremely well. He has the team in position to make a deep run in the playoffs without changing a single thing. However, the Phillies cannot afford to rest on their laurels around the trade deadline.

Philadelphia picked up Max Kepler as a free agent this offseason . Other than that, the Phillies did not make many moves in the winter. On paper, Thomson's roster can stand toe-to-toe with any team in the league on pure talent. However, Aaron Nola 's absence from Philadelphia's rotation has fans concerned. If he comes back at full health, no team has a better group of starters.

Thomson and the Phillies got to the NLDS before losing a heartbreaking series to their division rivals. They have been stewing on their defeat to the Mets for almost a year. That loss could make them more opportunistic at this year's deadline. Thomson and the front office want to ensure that it won't happen again.

Philadelphia is in great position to enter the playoffs with momentum. Making the right trades at the deadline could give them a leg up in an uber-competitive NL, though.

Here are three trades that the Phillies could make to catch the league off guard before the deadline.

Minnesota Twins Outfielder Harrison Bader

Phillies receive: OF Harrison Bader

Twins receive: OF Dylan Campbell

Almost every contender in Major League Baseball is interested in Luis Robert Jr., including the Phillies . However, the bidding war experts expect will break out for the Chicago White Sox outfielder could get really expensive really fast. For a team with a payroll as large as Philadelphia's, a cheaper option could accomplish the same goal without gutting their resources.

Bader has bounced around the league since spending the first five and a half seasons with the St. Louis Cardinals . However, he is not a player moved because teams do not like having him. Instead, his fielding and clutch hitting has made him a valuable asset. He was not great for the Mets in last year's postseason, but Bader hit five postseason home runs for the Yankees in 2023.

Bader is on a one-year deal worth just over $6 million . Bringing him in is little to no risk for the Phillies. With Max Kepler unhappy with Thomson and the organization, a replacement left fielder could eliminate that distraction. Bader is a veteran player who can give Philadelphia what they need without causing commotion.

Chicago Cubs Relief Pitcher Ryan Pressly

Phillies receive: RP Ryan Pressly

Cubs receive: RP Wen-Hui Pan

While trades within the same division are rare, ones between two teams in the same league happen all the time. After mulling over the deal, Pressly joined Chicago in a trade this offseason , but has moved into a setup role in Craig Counsell's bullpen. Despite the demotion, the veteran reliever has been just as effective as ever.

Matt Strahm , Orion Kerkering , and Jordan Romano have all spent time as Thomson's closer. However, the relievers as group could use one more addition to round out the group. Pressly is a proven player with plenty of postseason experience with the Houston Astros .

Pressly will be tough to pry away from Chicago, but not impossible. For a team led by a young star like Pete Crow-Armstrong , the Cubs' future is murky. Chicago is preoccupied with keeping him and Kyle Tucker on the team past this season. Despite their success, future security and a good prospect are attractive options to the Cubs, especially for a cheap veteran.

Pittsburgh Pirates Relief Pitcher Dennis Santana

Phillies receive: RP Dennis Santana

Pirates receive: SP Eiberson Castellano

Dennis Santana is having a good season. The Pirates are not. This trade is just as simple as that, really. Pittsburgh has fought rumors that they will trade Paul Skenes away all season. The team has been unable to get out of their own way all year. Unfortunately, that includes Santana, who was handed a four-game suspension by MLB earlier in June .

The relief pitcher was seen swinging at Pirates fans during a game delay. It is a bad look for a team that does not need any more negative publicity this season. Outside of that incident, Santana has pitched effectively. Pittsburgh has 33 wins on the season and Santana has saves in five of them to go along with a 1.57 ERA .

Santana's play this season, combined with the outlook on him right now, make him a perfect trade target. The Phillies could take advantage of the fact that the Pirates want to get rid of him and bring him in at pennies on the dollar. In a season where Philadelphia feels they are so close to a title, every little bit they can get out of all of their trades could make the difference.

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