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The low point between Brian Cashman and Derek Jeter as detailed in Andy Martino book ‘The Yankee Way’


Adapted from THE YANKEE WAY: The Untold Story of the Brian Cashman Era by Andy Martino, to be published by Doubleday on May 21, 2024. Copyright © 2024 by Andy Martino.

“I hear you talk [bleep] about me,” Derek Jeter, the Yankee captain, said to Brian Cashman, the general manager.

This was 2006 or ‘07 at the old Yankee Stadium.

“Well, D.J,.” Cashman answered. “If talking [bleep] is defined as me saying that you’re not treating A-Rod well, and your teammates have a problem with it, that they’re uncomfortable with that — I already talked about that to your face.

“If it’s about your defense and your lateral range, then I’ve already talked about that to your face. If it’s about you being so private and not letting people in, I talked to you about that. If that’s me talking [bleep] about you, then I have already dealt with you to your face.

He continued: “Where do you think this is coming from? The intel is coming back to me from our clubhouse. People you’ve won championships with are the ones telling me these things. People you respect.”

“Well, who?” Jeter said.

“I’m not saying who,” Cashman responded. “But it’s my job to confront it.”

THE YANKEE WAY: The Untold Story of the Brian Cashman Era by Andy Martino
THE YANKEE WAY: The Untold Story of the Brian Cashman Era by Andy Martino

Not many people spoke to Jeter that way, but that was Cashman’s style. And he and Jeter had been on opposite sides of a key issue for several years; their relationship was fraying, and they would not find a measure of peace with one another until Cashman attended Jeter’s Hall of Fame induction in 2021.

Of all the concerns that Cashman expressed, his primary worry remained that Jeter wasn’t supporting Alex Rodriguez.

In his third season with the Yankees, A-Rod was still struggling in the clutch, and still hearing boos from home fans. In fact, those boos were getting louder, and Cashman wanted Jeter to ask fans to ease up.

The sharpest visual representation of Jeter and A-Rod’s relationship came on August 17, 2006, when the two converged under a popup hit to the left side of the infield, failed to call for it, and watched as the ball landed on the infield dirt.

“Brian went to Jeter and said, ‘You’re captain of this team,’” says assistant GM Jean Afterman. “‘You don’t get to pick and choose who you’re captain of. You’re captain of everyone on this roster.’ That should have been incredibly persuasive.”

“I did confront him when Alex was getting booed,” Cashman says. “If you turn the clock back a couple years earlier when Jason Giambi was getting booed, he said publicly that fans shouldn’t boo Giambi. They should support our players. He liked Giambi so he defended him publicly. So I said, ‘How is it that you would do it for that one?’ Because his public stance on A-Rod was different. It was, ‘I can’t tell our fans what to do.’”

Jeter addressed these charges, sort of, in his 2022 documentary series The Captain. “What the [bleep] do you want me to do, man?” he said. “Yeah, I get it, but I don’t know what they wanted me to do, actually.”

Says Afterman: “In Jeter’s defense, I don’t know what anybody did expect him to do. I always enjoyed Jeter. I think he has a great sense of humor. But he’s not a warm and fuzzy guy for most of the world. That’s just not his style. I guess what everybody wanted was for him to defend Alex publicly, and that was a bridge too far for him.”

In 2009, at age 35, Jeter had enjoyed an excellent year, and was a key part of the Yankees’ World Series run. He batted .334 in 2009, with a .406 on-base percentage, 18 home runs and an .871 OPS — all upper-echelon numbers for a shortstop at any age.

The 2010 season brought an abrupt decline. In the final year of his contract, Jeter’s average fell to .270, his power faded and scouts inside and outside the Yankees organization continued to see slippage in his defense.

It was hardly the best platform year for free agency, but Jeter and his agent, Casey Close, did not think that should be the only factor; they felt that his iconhood should elevate his value.

In early talks, Cashman believed that the three-year, $45 million offer did just that, exceeding what he would pay any other shortstop of Jeter’s age and production. The Yankees, according to a team official, were also fielding unusual requests from Jeter’s camp for an ownership stake in the team and/or its cable channel, the YES Network.

Despite these differences, Cashman assumed that the negotiation would wrap up with relative ease — until, that is, he read quotes from Jeter’s agent that would reverberate for years to come.

It was a Sunday morning — November 21, 2010, to be exact — when Cashman woke up to learn he was in a public war with his captain.

That day, Daily News columnist Mike Lupica published a rare interview with the publicity-averse Close.

“There’s a reason the Yankees themselves have stated Derek Jeter is their modern-day Babe Ruth,” Close said. “Derek’s significance to the team is much more than just stats. And yet, the Yankees’ negotiating strategy remains baffling. They continue to argue their points in the press and refuse to acknowledge Derek’s total contribution to their franchise.”

Reading that, Cashman says, “we were all caught off guard and pissed off.”

In a meeting at the beginning of that offseason with Jeter, Close, Hal Steinbrenner and team president Randy Levine, Cashman agreed with everyone else to keep discussions out of the press, per Jeter’s wishes.

Cashman insists that he respected those wishes. While he says he can’t be sure that no one in the organization leaked, he cannot figure out which article set Close and Jeter off.

In fact, while preparing to sit for his interview for The Captain, on which Close was a producer, Cashman asked Yankees vice president of communications and media relations Jason Zillo to go back through clips from that time to make sure he wasn’t forgetting a provocative story in which he was quoted. Maybe it was his fault? But Zillo found nothing to indicate Cashman had provoked Jeter.

“I don’t know what it was,” Cashman says. “I still have no idea.”

In fact, it was not a single story that rankled Jeter and Close. Several articles reported from the GM meetings in Orlando, Florida the week before Lupica’s column contributed to a growing sense of irritation among Jeter’s team.

On November 17, Wallace Matthews on ESPNNewYork.com published a story headlined “Rough seas ahead for captain, Yanks?”

“If the New York Yankees could get Derek Jeter to agree to a three-year contract for $21 million per year, they would sign off on it today,” the piece began. “But they can’t get him to agree to that, which is why we are a week away from Thanksgiving Day and a deal that was supposed to be a slam dunk is still on the shot clock …

“Jeter, the source said, wants more. Four years, minimum, and preferably five or even six. Right now, it is a standoff, a dirty dance, a game of chicken in which one side or the other must eventually blink … Tell him the deal is three years at $15 million a year, take it or leave it,’ goes the hard-line approach. ‘Wait him out and he’ll wind up taking it. Where’s he gonna go, Cincinnati?’”

Cashman remains adamant that he had nothing to do with this or a few other stories about Jeter’s free agency prior to Close’s comments in the Lupica column.

Years later he can see how the “What’s he gonna do, go to Cincinnati?” comment in particular seemed inflammatory, but he strongly insists that it was not he who said it, and that he does not know who did.

After Lupica published Close’s comments, reporters reached out to Cashman.

“We responded,” Cashman recalls. “If shot at, we’ll fire back twice as hard. But we honored their ‘Hey, let’s keep it quiet.’ And one day we wake up and there’s Close going public. I didn’t go public in response until every writer came to me in response to Casey Close’s article with Lupica.”

On November 23, Cashman told Matthews, “We understand his contributions to the franchise and our offer [at that point, for three years and $45 million] has taken them into account.

“We’ve encouraged him to test the market and see if there is something he would prefer other than this. If he can, fine. That’s the way it works.”

In regard to Close’s comment about being “baffled,” Cashman told Matthews that he was “certainly surprised. We have actually gone directly face-to-face with Casey and Derek and been very honest and direct. They know exactly where we sit.”

No one in baseball had entertained the notion that Jeter, at 36 years old, would leave the Yankees. It was simply unfathomable. And now the GM was daring him to do just that.

“My fire off of ‘shop it if you don’t like it’ was a response to Casey Close and Jeter’s camp going public,” Cashman recalls.

Talks did not progress from there, and on November 29, Matthews quoted a source saying that Jeter and Close should “drink the reality potion.”

With both sides now upset, they convened in Tampa for another face-to-face meeting. Cashman, playing hardball by this point, enumerated the reasons why he felt Jeter did not deserve more money than the Yankees were offering.

Jeter fired back by asking Cashman who he would rather have playing shortstop. Cashman, put on the spot, named two younger stars, Florida’s Hanley Ramirez and Colorado’s Troy Tulowitzki. He hadn’t intended to go there, but Jeter had brought it up.

“I’m not going to sit here and listen to this [stuff],” Jeter said, according to his documentary.

That was the low point. Fearing that the deal could actually fall apart and Jeter would end up in another uniform before anyone knew what happened, both sides took a pause.

In early December they agreed to a three-year, $51 million contract, and held a downbeat news conference.

“I would be lying to you if I said I wasn’t angry about how some of this went,” Jeter said, standing at the lectern and frowning.

In his documentary, he elaborated.

“It changed my feelings about the front office,” he said. “I know now you were able to just throw me out. You were able to not treat me with the type of respect that I’ve shown you throughout my entire career. It’s not a two-way street. It was a reminder that it was a business.”

Jeter then changed his target from the “front office,” to Brian Cashman himself — who in 2024 is still wondering why he was the problem, when Close had been quoted first.

“Now I didn’t want to have too many conversations with Cash,” Jeter said. “Didn’t really want to speak to him, because I had lost that trust. Never say anything bad about him, but I didn’t want to see him.”

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