Rich’s Advice for the Yankees in Wake of Pinstripes’ Latest Playoffs Disappointment

The Yankees got swept out of the division series by the Rays without winning a game, and some in New York would love to see a job posting for a new general manager. Or a new manager. Rich, who reminded the room "I'm the real Yankee fan here," had a longer list of problems than one name on a door.

He started by defending Aaron Boone, at least partly. "It's a results-oriented business," Rich said, but Boone did not have Aaron Judge for two-thirds of the season, did not have Giancarlo Stanton for most of it, and was missing Carlos Rodón, Max Fried and Gerrit Cole at various points. Judge did not take a single swing in the postseason except in the cage, trying to come back from an injury he suffered after returning from the injury that cost him most of the year.

The bigger issue, in Rich's view, is a roster that does not fit together. George Lombard Jr. is "1,000% the Yankee shortstop of the future." Paul Goldschmidt, a Hall of Famer in Rich's eyes, is now a platoon first baseman who only plays against lefties. That creates a logjam with Ben Rice, who is no longer going behind the plate, which was how the Yankees used to get him into the lineup. And Rice may be the one bright spot. Rich called him "Aaron Judge 2.0, a left-handed hitting Judge," who crushed it in the postseason. "Forget about a pulse. He was a heartbeat of the team against the Red Sox," and the only consistent offense against a Rays staff that pitched around him to get to Cody Bellinger.

Then add Stanton, who does not play the field, and Spencer Jones in the outfield, and the question of what happens when Judge is healthy. "The roster, the way it is put together for the Yankees is a big huge ass mystery," Rich said. "And you're throwing that on Boone's lap."

He found poetry in the final out. The Yankees made the right maneuver with Trent Grisham, who came back, and it was "only fitting he made the last out against the Rays by swinging and missing because this lineup just doesn't put the ball in play enough." Against the Red Sox, the Yankees looked like world beaters. Against a Rays team that puts the ball in play, with pitching "not as well decorated or paid as the Yankee staff, but it's damn good," they were a totally different team. Rich did not believe the Yankees held a lead at any point in the series.

The money made it worse. The Yankees carry the third highest payroll in baseball. The Rays are 28th at $95 million. Stanton and Rodón alone will make a combined $56 million in 2026, more than half of the Rays' entire payroll, and all the Yankees got from them in the series was two pinch-hit at-bats from Stanton, both strikeouts in the only swings he had taken since April 24th. Rodón did not throw a pitch, which Rich understood with Cole, Cam Schlittler and Fried starting. But if you are building a roster to reach the World Series, "doesn't matter. You got swept."

Rich also refused to pin it on the fan who leaned over the wall on Anthony Volpe's fly ball, a fan he compared to Jeffrey Maier. Volpe's ball barely reached the wall and would have been a double, not a home run. The back page of the Post read "No Maier miracle this time," and Rich was not nostalgic. That old play was a blown call by Richie Garcia on the "Mount Rushmore of blown calls," and he did not understand why Yankee fans would celebrate it. "If we're hoping that the Yankees are rooting for a blown call to get to a game four, that ain't it."

So why does the GM have a lifetime contract, as one voice in the room asked? Brian Cashman had some great years, Rich said, and Hal Steinbrenner takes a different approach than his father, which is sometimes good. But the elder Steinbrenner once said, "You show me a guy who enjoys losing and I'll show you a loser," and Rich said that could describe his son right now, even as the franchise is winning on the revenue side and spending $300 million on players. The Dodgers, one spot above them, spend on surefire Hall of Famers who stay healthy and put the ball in play, for a manager in Dave Roberts who has "turned into a wizard." Meanwhile Rich watched Jazz Chisholm turn into "Knoblauch 2.0" on a key play and say he would do it again. "No, you should not do it again."

Judge's own words stung most. He said the Yankees should go all in to fill their holes, and that he signed back to "fight for a championship every single year." Rich called it "a killer for Yankee fans to see and hear him like this."

His prescription was simple. Shortstop is found. First base is handled, with Bellinger able to play there too. Rice has to get in somehow. So find people who put the ball in play at second base, "and if that's Volpe, so be it." At third, "give me somebody who doesn't hit home runs. I don't care." Someone who gets on base for all of these guys. "Put the ball in play for crying out loud," Rich said. "The Yankees got productive outs against the Red Sox. They were unbeatable."

Rich knows Mets fans are crying a river and that he can hear the tiny violin. He was just giving voice to what he has seen all year. "It's very frustrating."