How Brian Cashman Sold the Yankees’ Rebuild

TAMPA, Fla. — In the fourth week of July last year, while hosting Baltimore, Yankees general manager Brian Cashman reached an agreement to send Aroldis Chapman to the Chicago Cubs. It would be the first move in a partial dismantling of the club, a rebuild in New York representing one of the rarest roster-construction projects in baseball. But Cashman, and Cubs president Theo Esptein, had to wait. They had to wait for approval from Yankees ownership.

With the framework having been agreed upon, Chapman was still a Yankee as he entered a game on July 23rd against the San Francisco Giants at Yankee Stadium. He pitched the ninth and 10th innings.

“Chapman went two-plus innings, not something normally [that occurs] if you are going to execute a trade” Cashman told FanGraphs. “[Steinbrenner] waited 72 hours to green light it as he discussed it with his family. It was not an easy decision. I was keeping Theo on hold, essentially. I told him ‘I will let you know if ownership says ‘yes’.’ I said ‘I am recommending it. We’ll see what happens.’”

Chapman was still a Yankee as the club boarded a charter flight on July 24th to play a series in Houston. When the Yankees arrived in Houston, ownership had OK’d a type of plan rarely seen in New York. In a rare tactical retreat, the Yankees traded instant gratification — the hope of sneaking into the playoffs as a Wild Card — for the delayed variety. The Yankees had passed the Stanford marshmallow experiment. For Cashman, it had taken more than a year to lobby to adopt such a strategy, an approach that some believe has positioned the Yankees for their next sustained run of excellence.

The Yankees enjoy a No. 2 ranking in Baseball America’s recently released organizational talent rankings, after ranking 17, 18, and 18 in the three previous seasons, respectively. And the Yankees should have plenty of financial flexibility in the 2018-19 offseason, with a relatively paltry sum of $70 million in guaranteed salary on the books for ’19.

“It’s not the first time I’ve suggested that,” Cashman said of retooling. “It’s the first time ownership actually agreed to do it.”

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Cashman’s tenure with the Yankees is remarkable given the temperament and competitiveness of the late George Steinbrenner, given the demands of the market, and given the high bar of expectations constantly placed on the franchise. He began as an intern with the club in 1986 and is entering his 20th season as the club’s general manger. The experience has given Cashman something rare in New York: a blend of perspective and patience.

Part of his survival can be attributed to having never presided over a losing season as general manager, but four of Cashman’s first seven years with the club — when he was an intern and front-office assistant — actually were losing ones: all four years from 1989 to -92.

“When people say you can’t rebuild in New York I say, ‘You’re a liar,” Cashman told me. “We did.”

“I remind [ownership], I’ve been here a long time. I was here for a period of time when the last world championship was in 1978. Between 1996 and 1978, that’s a long period of time. I was here during the development of the Posadas, the Jeters, the Bernie Williams, Andy Pettittes, and Mariano Riveras… Brian Sabean was our scouting director, Bill Livesey was our director of player development and scouting. During that process, we rebuilt it. We rebuilt it in New York, and it led to an avalanche of success. When people say constantly like ‘Hey, they can’t rebuild, you can’t do that in New York,’ I don’t understand that, I was here. I lived through it. That’s powerful in my position to recall, retain, and remember. The most important thing for your fan base, which is your customer base, is to be honest with yourselves.”

Pinstripe Alley’s Harlan Spence has noted that some myth-busting is required to define the early 1990s as a true rebuilding effort. The Yankees still ran some of the game’s highest payrolls and held on to some of their best veteran players. (Steinbrenner had been banned from operating the club from 1990 to -92.) But the Yankees did trade stars on expiring deals like, Rickey Henderson and Dave Winfield, and benefited from a rare top-10 draft pick that led to the selection of Derek Jeter.

So while the late 1980s and early 1990s didn’t constitute a complete teardown and rebuild period, it was a time when the Yankees scouted and developed at a high level without fully flexing their financial muscle in regard to major-league payroll. They Yankees balanced the present with the future. They didn’t trade their top young prospects to improve their major-league club. As a result, the Yankees’ 1998 World Series title team enjoyed pre-arbitration seasons from Jeter, Jorge Posada and Mariano Rivera, who ranked 1st, 10th and 11th on the club that season in WAR. Pettitte, a 22nd-round pick in 1990, was in his first year of arbitration. The Core Four were, of course, homegrown products.

And amateur-player acquisition and development has only become more important over the last quarter century; the game has trended younger since PED testing was implemented. The practice of signing young stars to pre-arbitration extensions was pioneered in the early 1990s in Cleveland and has since proliferated throughout the game, eroding the number of quality free-agent seasons available for purchase. Those are all factors conspiring against the value found in free agency.

“We’re kind of in unfamiliar territory with the Yankees,” veteran first baseman Mark Teixeira told reporters last summer. “You can’t just win through free agency. That’s not the way it works anymore.”

To Cashman, it was clear two years earlier that the Yankees lacked the farm system capable of producing the pre-arbitration talent all elite teams — regardless of market size — require. Cashman believed the Yankees should dismantle to some degree. As early as the summer of 2014, Cashman was thinking about trading veteran players for younger assets.

“Turning the clock back with Robby Cano, it looked like he was going to stay with us. We pursued an extension with him ,and it wasn’t even close with what he wanted,” Cashman said. “He was, to me, someone we ultimately should have moved at the deadline but didn’t. So he left us as a free agent.”

The Yankees’ situation last summer was similar to what it had been in 2014 when Cashman began broaching the idea of selling off assets last season.

“I had recommended strongly that we push the reset button for our benefit,” Cashman said. “Probably starting in June, I had a lot of dialogue regarding what we should do and Hal Steinbrenner was telling me, ‘Well, I’m not thinking the way you are at this moment in time, but keep making recommendations.’ In my dialogue with ownership, [I said], ‘Every decision we make should try to put us closer to the next world championship. We want that to be in the upcoming season, but that doesn’t mean that is necessarily going to be the case.’ We have the most championships in the history of our sport, but we’ve been pursuing excellence for a 100 years plus and we don’t have a 100 championships. So there’s no embarrassment for not winning something [every season].”

En route to a fourth straight season of fewer than 90 wins, a season in which Cashman described his club as a “playoff pretender” when it fell to .500 in mid-summer, his conversations continued with ownership.

“Hal always says he’s open-minded,” Cashman said. “He has a lot of discussions with his family. He has a lot of discussions, with not just me, but our team president, general counsel, ticket director… He has a lot of areas of responsibility. He’s a pilot, so he uses the pilot analogy with me. He says, ‘Cash, you’re the director of baseball operations, you get to look at things at 5,000 feet. But as a pilot, I’m in charge of network ratings, ticket sales, advertising commitments to our sponsors, a whole host of things.’ So he had to look at things at 30,000 feet. Sometimes those decisions don’t match up with what I’d recommend, and I understand and respect that. Being an owner is not easy. We had dialogue throughout, and he eventually green-lighted what we did. I suspect as our team continued to not consistently perform, he eventually allowed us to do what we did.”

And after enjoying four straight seasons of 4 million-plus in attendance from 2005 to 2008, attendance declined steadily during the last three seasons. The Yankees drew 3.06 million last year, their fourth straight 80-something-win season. It was their lowest attendance mark at New Yankee Stadium, and their lowest in nearly 20 years, since 1998, Cashman’s first season as general manager. Consider this chart created by Sean Dolinar:

Following the Chapman trade on July 25 — a return headlined by Gleyber Torres, who has emerged as one of the top shortstop prospects in the game — the Yankees sent Andrew Miller to Cleveland on July 31 in exchange for highly rated prospects Clint Frazier and Justus Sheffield. The next day, Cashman sent Ivan Nova to Pittsburgh for prospects Tito Polo (an outfielder) and left-handed pitching prospect Stephen Tarpley. He also flipped Carlos Beltran to Texas for recent first-round arm Dillon Tate and right-handers Nick Green and Erik Swanson.

Gary Sanchez was already present…

“Every decision we did was not a ‘Go tear it down, globally,’” Cashman said. “It was ‘Bring everything you have to me [Hal Steinbrenner] on a recommendation basis, and I will decide.’”

Not every valuable asset, like, say, Masahiro Tanaka, was moved. But ownership did change its stance. Cashman said he’s not entirely sure what persuaded them to alter their position.

Perhaps the attendance decline shaped ownership’s decision, seeing that mediocrity was compelling fewer fans to travel to the stadium. Perhaps it was a realization that it’s more difficult to buy one’s way to contention in free agency in today’s game. Or perhaps the Cubs’ plan had an impact, a large-market club that was willing to take a dramatic step back, build up a collection of young assets, and then pour in financial resources to fill holes when a flood of young talent was nearing major-league readiness.

Whatever the case, the Yankee completed a rare teardown last summer, their most ambitious re-tooling since perhaps the early 1990s — or longer. And the early returns appear favorable, with a bevy of young bats offering promise.

“There is always this projection of where we might be in a year or two from now, and who may or may not be available, and of course people are always penciling in certain guys here,” Cashman said. “I think it’s in our best interest to develop star-caliber players within, so we don’t have to go to the marketplace. That’s what you want to do.”

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So what’s the reaction of a fan base that’s unfamiliar with rebuilding?

Cashman is a fan himself. He follows the New Jersey Devils and the University of Kentucky men’s basketball team. I was curious if he sensed fans have, to some degree, become more rational and less emotional — even in New York — when following a team that’s entered a rebuilding phase. Is there more understanding and acceptance of The Process?

“I am a fan of other teams and how they go about their business and in what they do, the decision making,” Cashman said. “I appreciate it, and I get it. Fan is short for fanatic. Fanatic means strong emotions come with it. Strong emotions have driven this sport, the attention and the interest, the potential money to be made… I’d be hard pressed to get a pulse on any change… I don’t know if anyone can psychologically diagnose whether a portion of the fan base is evolving from emotion to more practical.”

It’s also possible Yankees Nation will not have its patience tested. For starters, the performances of Sanchez, Gregory Bird and Aaron Judge are giving a glimpse of how promising that future can be. It’s possible the Yankees’ rebuild will not be that deep of a down period. The Yankees are forecast to win 81 games by FanGraphs’ projections; in our staff predictions, the Yankees were the most common No. 2 Wild Card pick in the AL. The lean times might not be all that lean for the Yankees.

“We got derailed, but we honestly assessed where we were,” Cashman said of last season. “It’s not an easy decision for [ownership] but I think it showed great leadership on their part in being willing to do it. I’m hopeful they are pleased with the early results, how the fan base is reacting, and how the foundation is significantly stronger because of it.”

The Yankees are perhaps following the Cubs’ model, at least to a degree. With large markets now operating at times like smaller-market clubs in accruing young assets, and willing to take a step back, it might mean we are entering an era when we will see more dynastic periods. Teams with the most financial might are now taking a longer-term view, which could improve their ability to better sustain success.

The Yankees are perhaps on a path to show us all, that, yes, you can rebuild in New York. You can rebuild anywhere and be better for it.