The New York Yankees are paying the price for one of Brian Cashman’s biggest missteps in years—letting Yoshinobu Yamamoto get away. What once felt like a near certainty has turned into a nightmare reminder of how far the Yankees have fallen from their “whatever it takes” identity. Now, as Yamamoto shines for the Los Angeles Dodgers and it’s in the conversation in the NL Cy Young race, Cashman’s decision to draw a financial line in the sand looks worse by the day.
When Cashman attended Yamamoto’s no-hitter for the Orix Buffaloes in September 2023, fans thought they were witnessing the start of something special. He stood and applauded from the front row, the image of a general manager scouting his next superstar. But a few months later, Yamamoto chose the Dodgers, signing a 12-year, $325 million contract that included opt-outs and performance incentives.
The Yankees reportedly offered $300 million with a higher annual value and flexible clauses, but they refused to exceed Gerrit Cole’s $324 million deal on principle. Cashman’s reasoning? Yamamoto hadn’t yet thrown a pitch in Major League Baseball. That “logical” restraint might have made sense in theory, but baseball’s free-agent market rarely rewards caution — and this one proved costly.
Dodgers Went All-In, Yankees Played It Safe
The Dodgers knew precisely what they were doing. They didn’t just sign a pitcher. They invested in a global icon who could anchor their rotation for a decade and strengthen their brand across continents. By pairing Yamamoto with Shohei Ohtani, they cornered both the competitive and marketing sides of the sport.
Yamamoto rewarded that faith instantly. Through his second MLB season, he’s posted a 2.73 ERA across 173.2 innings, dominating October with a 5-1 postseason record and a 2.47 ERA in six career playoff starts. His latest masterpiece, a World Series complete game where he retired 20 straight batters, cemented his status as one of the best pitchers on the planet.
The Yankees, meanwhile, settled for Max Fried, signing the lefty to an eight-year, $218 million deal. Fried’s résumé was strong, but he was entering his 30s, and his postseason collapse against the Blue Jays only underscored the gap between him and Yamamoto. While the Dodgers are celebrating a potential Cy Young winner, the Yankees are left analyzing “what if.”
Cashman’s Legacy Takes Another Hit
This wasn’t just about one missed free agent—it’s a symptom of a larger problem under Cashman’s leadership. The Yankees have repeatedly come up short in securing elite talent when it mattered most. They did it with Freddie Freeman. They did it with Blake Snell. And they did it again with Yamamoto.
For an organization built on star power and swagger, that shift toward restraint has cost them both credibility and championships. The Yankees used to set the market. Now, they’re being used by agents as leverage to drive up offers elsewhere.
A year after Yamamoto’s decision, the contrast couldn’t be sharper. The Dodgers are in the World Series, their rotation anchored by the Japanese ace the Yankees once courted. Cashman, meanwhile, is left defending another offseason of “smart spending” that produced nothing but regret.
Had he gone just $25 or $50 million higher, Yamamoto could’ve been dominating October in pinstripes instead of Dodger blue. Instead, the Yankees’ general manager once again chose logic over legacy. That might be the decision that finally defines his era.
Like Heavy Sports’s content? Be sure to follow us.
This article was originally published on Heavy Sports
The post Yankees Paying the Price After Cashman Failed to Land World Series Hero appeared first on Heavy Sports.