On Wednesday, the New York Yankees fell 4-3 to the Tampa Bay Rays in the ALDS. It marked their third loss in a row and the end of October baseball for the Yankees. The latest playoff disappointment has ignited questions about the franchise’s roster-building ability. The Yankees must evaluate how expensive contracts, trade decisions, and player-development results have delivered for the team in the last couple of years. Meanwhile, a veteran Yankees analyst and broadcaster has demanded a change inside the clubhouse.
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“Something has to change. What it is, I don’t know. I’m not smart enough.
But something has to change,” said Michael Kay on The Michael Kay Show, per Everything Yankees on X. “Either the type of player you’re getting, the philosophy that you’re teaching, something has to change. You can’t keep doing this and expecting, ‘Okay, we’ll run into one.'”
Kay’s frustration with the current team is understandable. With this year’s exit, the Yankees’ World Series drought has been extended to 17 years. New York scored only 5 runs in the three games of the 2026 ALDS.
For Kay, the problem extends beyond one series. Kay spoke about the areas the front office must address to bring back a championship in the Bronx.
The Yankees have the third-highest payroll in baseball. But a high payroll does not automatically translate into wins. While the biggest spender in MLB, the Dodgers, is aiming for a World Series three-peat, the New York Mets have the second-highest payroll. Yet the Mets did not even finish above .500. They finished last in the NL East.
For the Yankees, one such example of roster burden is DJ LeMahieu. After winning the American League batting title in 2020 with a .364 average, LeMahieu signed a six-year, $90 million contract extension. However, his production at the plate declined rapidly, forcing the Yankees to DFA him. But the Yankees still have to pay him the remaining $22 million he owed the team.
The same question surrounds all the Yankees’ long-term commitments. The players might be delivering now, but if they ever suffer a sharp decline, the Yankees would have no choice but to carry those contracts to the end. For instance, Gerrit Cole’s nine-year, $324 million deal is signed through 2028. Aaron Judge’s nine-year, $360 million contract adds another major commitment to the payroll.
With all this money tied up in keeping veteran players, the Yankees ultimately have a limited amount left to sign new players.
Player development is also a relevant concern. Anthony Volpe, a first-round selection in 2019, became New York’s starting shortstop in 2023, but his offensive consistency has remained under scrutiny. Austin Wells, drafted in the first round in 2020, has also experienced difficulties at the plate. His batting average fell from .229 in 2024 to .186 in 2026. To address such issues, the Yankees can focus on their farm system.
Kay also spoke about the 2017 season, when the Yankees lost the ALCS to Houston in seven games. The Astros later won the World Series, but they were involved in a sign-stealing scandal. But it does not change New York’s inability to advance.
“I know a lot of people in the organization felt they should have been in the World Series in 2017. But they came up against a team that cheated… So maybe they would have been in the World Series that year. Maybe they would have won the World Series that year. Maybe. But you didn’t,” said Kay.
With another season ending short of the ultimate goal, general manager Brian Cashman and the organization’s leadership face renewed pressure to assess their contracts, roster depth, trades, and player development. For a franchise with 27 World Series championships, the question is no longer simply whether it can spend enough to compete. It is whether the organization can turn those resources into a balanced roster, better long-term decisions, and ultimately, another championship.