Note: This is a three-part article series. It is important to know the data set analyzed dates are from 2015 to present day. Also, long-term extension for this purpose was defined as 5+ years.
The New York Yankees have long been synonymous with big spending, marquee free-agent signings, and a “championship or bust” mentality. Managing General Partner Hal Steinbrenner has repeatedly expressed a desire to lower payroll while maintaining a “championship-caliber roster”. In an evolving Major League Baseball (MLB) landscape, New York must alter their outdated approach on roster construction.
Unlike forward-thinking teams such as the Atlanta Braves, Boston Red Sox, San Diego Padres, and Arizona Diamondbacks, the Yankees have largely ignored the proven modern trend of signing young players to early extensions. This has led to situations where homegrown stars reach free agency and demand massive contracts—sometimes forcing the Yankees into expensive, long-term commitments or losing key players altogether.
Aaron Judge is a prime example. The Yankees failed to extend Judge before he reached free agency, ultimately signing him to a massive nine-year, $360 million contract in 2022. Had the Yankees approached an extension earlier in his career, they could have secured him for far less, avoiding the risk of losing him or overpaying in his 30s.
Steinbrenner and General Manager Brian Cashman have been notoriously hesitant when it comes to handing out long-term extensions. Instead, the Yankees often wait until players reach free agency, leading to costlier contracts or key departures. In fact, over the past decade, the Yankees have only handed out a single long-term extension. That came in the form of a disastrous seven-year, $70 million to Aaron Hicks in 2019. However, the reluctance to embrace extensions has arguably hurt the team more than one bad contract ever could. While other organizations extend their stars early, securing cost control and roster stability, the Yankees often let players enter free agency, where bidding wars drive up prices.
The Yankees must evolve if they want to remain perennial contenders without breaking the bank. Early contract extensions offer a clear solution to ownership’s payroll concerns while ensuring roster stability. Their resistance to this approach has led to costly contracts for players already past their prime, further complicating Steinbrenner’s payroll goals. If the Yankees fail to modernize their approach, they further risk losing their competitive edge in a rapidly ever-changing MLB landscape.
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