New York Yankees Must Respond To Dylan Cease’s $210 Million Contract

Tampa, FL: New York Yankees owner Hal Steinbrenner speaks during a press conference regarding changes to the Yankees facial hair policy during spring training at George M. Steinbrenner Field in Tampa, Florida on February 21, 2025. (Photo by Thomas A. Ferrara/Newsday RM via Getty Images)

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The New York Yankees have made it abundantly clear that free agent outfielder/first baseman Cody Bellinger is a top priority this offseason. Even if a reunion with Bellinger were to occur alongside center fielder Trent Grisham after accepting a one-year, $22.025 million qualifying offer, the Yankees would be at status quo from last season and still a distance behind the Los Angeles Dodgers and Toronto Blue Jays. Right-handed pitcher Dylan Cease has put additional pressure on the Yankees after agreeing to a seven-year, $210 million contract with the Blue Jays. Confidence never wavers when it comes to spending on payroll, but it seems as if the Yankees are struggling with how $300 million has become the cost of doing business in Major League Baseball if you’re a large market franchise. An $8.2 billion valuation according to Forbes, the Yankees need a blockbuster trade or something bold to occur in free agency given the intense competition for premium talent and constantly being stuck in neutral when it comes to achieving success in the postseason.

Yankees And Payroll Scrutiny

Hal Steinbrenner, managing general partner and co-chairperson, is fiscally conscious by nature and runs the Yankees with prudence rather than emotion. Steinbrenner knows the Yankees cannot serve as an exit strategy for several franchises across Major League Baseball who are suffering from self-inflicted wounds courtesy of egregious contracts. Giancarlo Stanton is a constant reminder for Steinbrenner even though the 36-year-old designated hitter has had periods of excellence sprinkled throughout his injury-plagued eight seasons in the Bronx. The Yankees’ payroll is always under scrutiny whether it is for Competitive Balance Tax purposes, overspending on marginal talent or missed opportunities in free agency. Some are still perplexed as to why the Yankees only flirted with first baseman/outfielder Bryce Harper and third baseman Manny Machado in free agency prior to the 2019 season.

Return on investment for the Yankees is defined in a vastly different manner than nearly every franchise in Major League Baseball, especially after spending $319 million on payroll last season. However, Steinbrenner cannot publicly complain about $100 million payments to New York City every February 1st without giving a detailed explanation. It’s not a simple income statement example to elicit sympathy for a global sports juggernaut. Instead of expressing frustration with questions pertaining to the Yankees’ budget, Steinbrenner should educate everyone on how the franchise saves millions through a payment-in-lieu-of-taxes (PILOT) agreement. Let’s not forget the millions the Yankees have saved on right fielder Aaron Judge’s nine-year, $360 million contract given how compensation doesn’t align with historic performances on an annual basis.

It’s hard to fathom how the Yankees have become stagnant amid tremendous success in terms of revenues and on-field performance. According to Sports Business Journal, Yankee Stadium generated $339.5 million in aggregate ticket and premium suite licensing revenue through the end of September. Regardless of revenues reported in the disclosure pertaining to Yankee Stadium bonds, the sizable gap that already exists between the Dodgers and Yankees is widening and payroll isn’t the only culprit. The Dodgers are operating under a different mindset when it comes to winning as the Yankees are in dire need of new voices and fresh ideas. The Blue Jays are also making matters worse after eliminating the Yankees in the 2025 American League Division Series and nearly winning the franchise’s first World Series since the 1993 season after a thrilling seven ball games versus the Dodgers.

Yankees Need To Question How Money Is Being Spent

Steinbrenner’s comments in support of a salary cap and lowering payroll will not deter the Yankees from spending money and having one of the highest payrolls in Major League Baseball next season. The real question is whether the money is being spent wisely based on the recommendations of Brian Cashman, senior vice president, general manager. It’s nearly impossible for the Yankees to delicately manage the pursuit of World Series glory without overspending on payroll. Besides legitimate questions pertaining to accountability and responsibility when it comes to roster construction and player development, a common criticism of franchise leadership is the absence of passion. It is unfair to compare father to son, but George Steinbrenner’s flaws and indiscretions were mostly absolved due to his unrelenting passion for domination while treating the concept of winning as if it were oxygen.

Amid recent trade rumors regarding Corey Seager of the Texas Rangers, the Yankees were immediately linked to the 31-year-old shortstop based primarily on the ability to absorb the remaining six years and $186 million remaining on the contract according to Cot’s Baseball Contracts. The rumors only intensified after the Rangers traded second baseman Marcus Semien to the New York Mets in exchange for outfielder Brandon Nimmo. Besides age and contract status, complexity surrounds Seager as he is an elite ball player who has an extensive injury history like Bellinger. However, it hasn’t stopped fans from thinking about signing Bellinger and trading for Seager. It could be viewed as two for the price of free agent Kyle Tucker, a 28-year-old right fielder who is projected to secure a contract of at least $400 million in value.

Yankees Need To Embrace Creativity

The Yankees need to embrace creativity this offseason, and it goes well beyond the pursuit of Japanese right-handed pitcher Tatsuya Imai who has been posted by the Saitama Seibu Lions of Nippon Professional Baseball (NPB). Would the Yankees be willing to entertain trade conversations involving Jasson Domínguez, Spencer Jones, George Lombard Jr., Anthony Volpe, Ben Rice and Will Warren? What if Detroit Tigers left-handed pitcher Tarik Skubal miraculously became available and the asking price was at least four of the previously mentioned ball players? Would the Yankees say no because Skubal will command a $400 million contract in free agency after renting his services for one season?

The New York Yankees need to send shockwaves throughout Major League Baseball, and it has nothing to do with dominating the offseason headlines. It’s about demonstrating a passion for winning and spending wisely on talent without complaining about payroll. A swift response is needed to the Toronto Blue Jays signing right-handed pitcher Dylan Cease to a seven-year, $210 million contract. A series of transactions should focus on pitching excellence, stellar defense, smart baserunning, high contact and low strikeout ball players. By no means will the process be easy as is often the case with a series of transformative decisions. Hal Steinbrenner values consistency and stability, but the time has come for change given how intense competition is pushing the Yankees aside as the Bronx is no longer the epicenter of Major League Baseball’s universe.