4 All-Stars that could've changed the course of Yankees history, 1 that ruined it

The 2026 Home Run Derby was the most electrifying event in years, and on Tuesday night the All-Star Game will have big shoes to fill. Although some of the game's premier stars won't be playing (Shohei Ohtani, Aaron Judge, Nick Kurtz, Byron Buxton Yoshinobu Yamamoto, Paul Skenes, Jacob Misiorowski, Cam Schlittler, and others), there's still plenty of top-tier talent that'll have fans glued to the screen.

As for Yankees fans, though Ben Rice and Cody Bellinger are in the starting lineup, the 2026 All-Star Game features one former Yankee and a number of free agent misses that could have changed the course of team history during the Judge era. There's also one that could be held accountable for the team falling short over that same span.

So when you're watching on Tuesday night, don't get too emotional. The Yankees still have a very good team this year and could make a run. There's no sense in raging against Brian Cashman unless we absolutely need to.

2026 All-Stars that could've changed the course of Yankees history

Juan Soto

The obvious. The Yankees offered Soto $760 million and he opted for $765 million guaranteed with the Mets (and $805 million total in escalators). So far, his tenure in Queens has been an absolute disaster, whereas his lone year with the Yankees featured the Bombers' first World Series appearance since 2009. If he was on last year's team or this year's team, who knows how different life would've been. We're over it, but we miss him.

Kyle Schwarber

Cashman's white whale who was ... totally attainable but the Yankees never pulled the trigger? We know the fit was imperfect because of Giancarlo Stanton's decade-long presence, but the Yankees somehow didn't have enough lefties in their lineup for years ... during the same timeframe when Schwarber was affordable. He was DFA'd in 2021! He's been the league's most prolific home run hitter besides Aaron Judge since 2022, and if he played half of his games at Yankee Stadium he'd probably have at least 25 more to his name. For whatever reason, it just wasn't meant to be.

Bryce Harper

Why the Yankees never contacted Bryce Harper during his free agency tour in 2018, we'll never know. He grew up a Yankees fan. He openly admitted he wanted to be a Yankee. Once again, the Stanton trade prevented the front office from making a more reasonable investment. Harper was heading into his age-26 season when he was a free agent and totally would've been worth a 13-year contract. At the time, Cashman said the Yankees had too many outfielders and that he wouldn't consider moving a talent of Harper's caliber to first base. Care to guess what position Harper plays now?

Freddie Freeman

We'll never know if Freeman would've come to the Yankees with the Dodgers were in hot pursuit of him ... but this was yet another instance where the Yankees didn't even try (Freeman's words, not ours!). Jon Heyman reported Freeman wanted to return to Atlanta, but if that wasn't on the table he'd prefer LA. Freeman expressed he spoke to Cashman, but the Yankees never made an offer. The Yankees pivoted to Anthony Rizzo, which was disastrous for so many reasons, and ended up paying him $63 million from Aug. of 2021 through the end of 2024. Freeman is on a $162 million contract over the course of six years and is 10 times the player Rizzo was during that span.

Honorable Mention: Yoshinobu Yamamoto, even though we know he always preferred LA and used the Yankees as leverage

Aroldis Chapman ruined the Aaron Judge era in multiple Yankees postseasons

Aroldis Chapman

The worst. The absolute WORST. The guy who remembered how to throw strikes the moment he arrived in Boston after years of erratic pitching. Chapman was a heinous postseason performer for the Bombers, blowing the 2017 and 2019 ALCS matchups against the Astros (who were cheating, but still). And then there was Mike Brosseau's home run with the Rays in 2020.

Chapman was overpaid and ended up leaving the Yankees unceremoniously in 2022 when he refused to show up for a workout because he wasn't guaranteed a postseason roster spot following a tattoo infection. Very cool that he's a back-to-back All-Star in his age-37 and 38 seasons with the Red Sox, though.

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