Inside The Pinstripes

Yankees Linked to Surprising Phillies Outfielder

The New York Yankees could offer a deal to this free agent coming off a year with the Philadelphia Phillies.
Oct 6, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies left fielder Max Kepler (17) runs to third base after hitting a triple against the Los Angeles Dodgers in the eighth inning during game two of the NLDS round for the 2025 MLB playoffs at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images
Oct 6, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies left fielder Max Kepler (17) runs to third base after hitting a triple against the Los Angeles Dodgers in the eighth inning during game two of the NLDS round for the 2025 MLB playoffs at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | Bill Streicher-Imagn Images

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The New York Yankees have been working all offseason to make a massive signing in the outfield. Their main target is to bring back heavy-hitting veteran Cody Bellinger, but negotiations have yet to prove fruitful for the club. Now, a new idea has emerged, with Philadelphia Phillies left fielder Max Kepler looking for a new deal.

Kepler, entering his 12th year in the majors, played the first 10 seasons of his career win the Minnesota Twins before signing with the Phillies as a free agent on a one-year, $10 million deal. He played 127 games with Philadelphia in 2025, slashing a .216/.300/ .391 for an OPS of .691 and hit 18 home runs.

While his 2025 stats are an improvement from a 2024 season marred by injury, Kepler certainly didn't become the offensive cornerstone Phillies president of baseball operations Dave Dombrowski hoped he would be last year. That fact makes a reunion with Philadelphia unlikely, but also makes a big deal with the Yankees even more unlikely.

Should the Yankees Sign Max Kepler?

Then there's the issue of handedness. Yankees general manager Brian Cashman recently went on the record as describing the Yankees as "left-handed dominant throughout [their] lineup." Adding Keppler would add yet another left-handed hitter to the list consisting of Austin Wells, Ben Rice, Jazz Chisholm Jr., Ryan McMahon and Trent Grisham. Bellinger is also left handed, but offers more consistentcy and better stats across the board then Kepler.

One of the chief concerns about Bellinger comes from his age. After a great season to start his 30s, many are expecting Bellinger to want a big, lengthy contract that some analysts have tabbed as worrisome. The Yankees, or any team that signs the outfielder, run the risk of having him on contract past his prime.

Philadelphia Phillies left fielder Max Kepler
Oct 4, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies left fielder Max Kepler (17) hits a double against the Los Angeles Dodgers in the ninth inning during game one of the NLDS round for the 2025 MLB playoffs at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images | Bill Streicher-Imagn Images

Kepler represents a similar conundrum, as he'll be 33 when the 2026 season begins. However, Kepler would likely be on a much smaller contract for only one year, similar to the one he signed with the Phillies, which makes him less of an investment.

While Kepler looks like a possibility the Pinstripes could entertain, he's likely only an emergency option. The Yankees are reportedly deep into talks to bring back Cody Bellinger and have made inquiries about Chicago Cubs outfielder Kyle Tucker as well. Kepler is likely only in the picture if talks with Bellinger fall apart or they deal their best trade capital elsewhere.

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Delilah Bourque
DELILAH BOURQUE

Delilah Bourque is a writer and copyeditor based out of Pittsburgh, PA. She received her Bachelor's degree from the University of Pittsburgh in 2021. After a few years in corporate marketing, she joined On SI as a full-time copyeditor and contributor to the New York Yankees On SI, as well as occasional contributions across the Pittsburgh Pirates and Pittsburgh Steelers on SI.