Aaron Judge, the New York Yankees captain and three-time AL MVP, played 66 games in 2026 and none in October, and the lineup hit .130 in a sweep. Seventeen seasons after the 2009 World Series, the Yankees’ payroll above $300 million still has no new ring to show for it.

Prominent MLB agent Scott Boras addressed the franchise’s title-less stretch during an appearance on SNY Yankees. Having negotiated ace Gerrit Cole’s nine-year, $324 million deal with the club, he knows the front office well. His message was blunt.

“There are many things about what the Yankees do that I can tell you they’ve done right,” MLB agent Scott Boras said on SNY Yankees. “But on the other side, have they achieved what they want to achieve? You know what? The group of people and the ownership they have should achieve what they want to achieve. I’m sure they have to look at that every day and say, ‘I have to do more, or I have to do things differently. But the one thing I can’t do is just repeat what I’ve been doing.’”

Boras is not wrong, because the Yankees met nearly every contender input. Payroll sat above $300 million, third-highest in MLB, and 13 postseason trips have come since 2009. The 17-year gap spans 1979 to 1995, ending once homegrown talent matured. Boras made a similar ownership argument two winters ago.

“I’m going to commit my career to it,” Boras said of outfielder Juan Soto’s free-agent mindset in comments carried by SNY in November 2024, “and I want the owner to commit his resources to it.”

Soto signed a 15-year, $765 million deal with the New York Mets weeks after the Yankees lost the 2024 World Series 4-1 to the Los Angeles Dodgers. Spending was never the issue, but availability was.

Judge is the clearest example, a three-time AL MVP signed through 2031 on a nine-year, $360 million deal who managed only 66 games because of rib and calf injuries. The pitching staff dealt with its own absences.

Gerrit Cole, the Yankees’ ace, worked 127 innings after Tommy John surgery. Left-hander Max Fried logged 112 2/3 with an elbow bone spur, yet the rotation still led MLB with a 3.30 ERA, paced by right-hander Cam Schlittler, who went 14-6 with a 1.95 ERA and 239 strikeouts as an AL Cy Young finalist.

The bats failed in a different way.

The lineup scored five runs in three ALDS games against the Rays and slid from first in MLB wRC+ in 2024 and 2025 to 14th in 2026. Those numbers look worse considering who ended the Yankees’ season.

The Rays advanced on a payroll of about $95-98.5 million, roughly a third of the Yankees’ figure, which sharpens Boras’s point about turning payroll into titles.

That gap puts the focus on the people who build and run the roster. Owner Hal Steinbrenner still kept general manager Brian Cashman for a 30th season and manager Aaron Boone for a 10th, so change must come elsewhere.

That change has already started on the coaching staff, as hitting coach James Rowson left for the San Francisco Giants, bench coach Brad Ausmus took the Houston Astros managing job, and field coordinator Tanner Swanson became the Seattle Mariners bench coach.

The roster has holes too. Closer David Bednar faces a $23.15 million qualifying offer, second baseman Jazz Chisholm Jr. is a free agent, and payroll projects near $338.9 million, past the $247 million tax line. Money alone has not solved this before.

The 1990s Yankees showed another route, ending their drought by letting shortstop Derek Jeter, reliever Mariano Rivera, and outfielder Bernie Williams mature before adding targeted veterans. Cashman is retooling a 93-win roster around aging stars, though younger help is arriving.

That younger help is already visible. Slugger Ben Rice broke out, and prospects George Lombard Jr., Spencer Jones and Elmer Rodriguez debuted in 2026, giving Cashman more lineup options around Judge and designated hitter Giancarlo Stanton, who returns for 2027. Those options frame the outlook ahead.

Judge will get more designated hitter reps in 2027, Stanton returns for his final contract year, and the staff will add several new coaches. Whether that qualifies as the different approach Boras described will be settled next October.

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