The atmosphere in New York was filled with anticipation when their newest star acquisition stepped into the spotlight. Max Fried, the left-handed ace whose talent was undeniable, was signed by the Yankees for what was the largest contract for a pitcher—a whopping $218 million! It was a deal that had fans and analysts alike buzzing with excitement, imagining Fried’s electric arm in pinstripes. However, beneath all the glitz of this historic agreement lies a looming question: Is this deal worth it? Is it as much of a risk as it is a reward?

As it turns out, Fried’s contract quickly birthed attention beyond just the Yankees fans. Fox Sports, in its analysis of the riskiest contracts of the 2025 offseason, included Fried’s massive deal on their list. Despite the immediate connection and bond he made with the team, his injury history made the $218 million commitment one of the most precarious in the game. His past and the extended length of the contract have raised eyebrows on whether the Yankees are taking on more risk than they bargained for.

And why wouldn’t it raise concerns? Max’s track record is not one to dismiss easily. Over the years, the left-hander has battled an unsettling series of injuries that have kept him sidelined for a long period. It started with a blister on his middle finger in 2018, which sent him to the injury list, followed by a strained left groin in 2019. The setbacks continued into 2020 with a muscle spasm on his left side and, in 2021, a strained right hamstring. Then came the concussion in 2022 and a series of injuries in 2023—strained left hamstring, strained left forearm, and another blister on his left index finger.

While Fried’s talent and potential are undeniable, it’s the injuries that raise concerns. The Yankees are no strangers to high-stakes contracts, but with this $218 million deal, they’re betting on Fried’s ability to defy the odds. The pressure would be on him to stay healthy and perform. His massive contract might have the potential to be a reliable pillar for the Yankees. But one wrong step, one unpredicted injury, and this deal could very well go down as one of the riskiest moves in baseball history.

Max Fried explains why he chose the Yankees.

Max Fried was at a crossroads in his career, where free agency had him pondering his next destination. Despite having several offers from different teams, a certain team had him intrigued in a way that others couldn’t: The New York Yankees! A franchise synonymous with championship glory. For Fried, it was more about just the terms, it was about winning.

“I was walking through the clubhouse and there’s three words that were put up on the wall- Prepare, Compete, and Win,” Fried recalled during his introductory press conference in the Bronx. The words deeply resonated with his competitive core; this was no ordinary team but the Yankees, a team whose legacy is built on relentless drive and unwavering commitment to win.

In 2024, Fried posted a 3.25 ERA and 166 strikeouts with a 1.16 WHIP, proving his worth as a top-tier starter. But for him, it was never just about the numbers. “Winning is a big priority for me,” he said. Now with a record-breaking $218 million deal, Fried’s arrival in New York is welcomed with massive expectations. While the deal has its own share of risk involved, his commitment to winning gives the Yankees hope that he’s exactly what the franchise needs to add another championship banner to their rich history.