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Inside the three days leading to the Yankees’ selloff

Back in December of 2015, shortly after an aging Yankees roster limped back into the locker room after being silenced by Dallas Keuchel and the Astros in the Wild Card Game, team president Randy Levine spoke on the state of the franchise.

“What has to be noticed here, unlike very few teams, what we’ve done, is we can’t rebuild here,’’ Levine said. “That’s not what we’re about. We’re trying to win every year and we’re trying to get younger and transition. Most teams, they have two, three, four years to rebuild. We don’t do that.’’

The Yankees don’t rebuild, but they wanted to get younger. Can there be one without the other? Surely some short-term success would have to be sacrificed if the Yankees were to establish a brighter long-term outlook for themselves heading into the 2016 season. But even as losses mounted, and with it the gap swelling between the Yanks and a playoff spot, the direction of the franchise heading into the trade deadline appeared clouded. The Yankees don’t fold. They don’t sell. And they definitely don’t rebuild.

“One of the executives from another team gave me a call and said, ‘Do you think these guys are really going to sell?’” ESPN’s Buster Olney told Pinstripe Alley of the talk around the league heading towards the 2016 trade deadline. “Nobody was used to that. No one had ever seen a Yankee team that would think about selling off players midseason. I remember covering them in 2000 when they made nine trades to add. That’s what everyone was used to.”

By July 25, it became clear that this wasn’t 2000. The Yankees, 7.5 games back in the division at the time, pulled the trigger on a trade of Aroldis Chapman, who was dealt to a Cubs team in desperate need of bullpen help to end a painful title drought. The prized return was top prospect Gleyber Torres, while also bringing back Adam Warren to appease Hal Steinbrenner and his desire to keep veteran talent on the roster. The trade brought back a massive haul, but still didn’t indicate that the Yankees were expected to unload veteran talent before the deadline passed, particularly their other superstar lefty reliever Andrew Miller.

“I believe they got permission to make a move on Aroldis Chapman relatively early because he was a free agent in the fall,” Olney said. “But because Andrew was under contract, it was more complicated.”

There was another hurdle to clear for the Yanks to commit to an all-out sell: the team was actually playing better.

Heading into the final series of July, a three-game set against the Rays at the Trop, the idea of selling off top-tier talent to acquire young, promising prospects was considered a possibility. But after winning eight of their last 11 games to pull within six games of the division lead on the loss side, questions lingered about if the Yankees would actually do the unthinkable and wave the white flag, potentially dooming themselves to their first losing season since 1992. Following a loss to the Astros, this three-game set in Tampa, wrapping up just before the trade deadline, would be pivotal in determining the fate of the franchise for years to come. Would Chapman be the only trade chip to be parted with, or would the financial powerhouse and World-Series-or-bust Yankees actually commit to a reload?

“As teams were having conversations with the Yankees, people wondered if it would be a lot of talk that led to nothing,” Olney said. “On one hand, Brian Cashman was very serious about it, but it was very apparent to folks from other teams that he was going to have to get ownership to go along.”

July 29 — Rays 5, Yankees 1

The Yankees knew if they were to stay in the race and give ownership a glimpse of promise heading into the final two months of the season, they would have to take care of business against the last-place Rays, who were at the time 22 games below .500.

“We know what we have to do and it’s no time to let our guard down,” Mark Teixiera told the New York Post heading into the Tampa series. “We are going to take this series like every one since the break knowing we should win it and we have to win it if we want to stay in this.”

Well, the Bombers’ offense didn’t echo Teixeira’s rally cry, especially not in game one. The Yanks lost to Jake Odorizzi while potential trade chip Ivan Nova was knocked around for five runs in 4.1 innings in a 5-1 loss. With two straight losses, the Yankees’ postseason odds had dipped below eight percent, and before the game, Cashman was reportedly receiving calls about Miller, specifically from the Nationals, who offered Lucas Giolito, one of the top-ranked pitching prospects in baseball, in return. The Yanks wouldn’t take the deal, but were fielding calls from other teams, and Cashman remained adamant about dealing Miller, who was under team control through 2018 and could bring in a Chapman-like haul.

Seattle Mariners v Chicago Cubs Photo by Joe Robbins/Getty Images

“Part of the reason Brian felt it was the right time to move those guys because they were relievers...and it’s a volatile asset,” Olney said. “In the winter, teams don’t usually overpay for relief help...and Brian understood that he had a situation where the one time a year teams are willing to pay big for relievers is in the weeks leading up to the trade deadline. Not only was the timing right in that respect, but both of those guys were also pitching great. Everything fell into place for them to have relatively high demand compared to other relief pitchers.”

July 30 — Rays 6, Yankees 3

The losing streak reached three games after a 6-3 defeat to clinch a loss in the series to the Rays, dropping playoff odds to under five percent, per FanGraphs. The hot streak that surrounded the Chapman trade was a distant memory, though even during that mini surge, Cashman never questioned what he thought was best for the franchise.

“I know as a member of the media here that you would write about how they’re having success and that could raise questions and what would the fans think, but I don’t think Brian ever wavered on what was the best course of action,” Olney said. “Brian, especially in the last 15 years, has been rooted in the data, and FanGraphs has this great thing where they go day-by-day on a team’s chances to make the playoffs, and I think Brian absolutely was aware of those numbers and believed in those numbers. But on the other hand, you have Hal Steinbrenner who respects and understands the fanbase’s perspective that ‘we’re the Yankees and we always go for it.’”

The numbers didn’t lie, and the recent performance on the field backed them up. As calls continued to come in asking about Miller, Cashman had the go-ahead from ownership to move forward with the fire sale. This wasn’t the trade of a pending free agent, but of an All-Star reliever with two more years of team control. The Yankees were really doing this.

July 31 — Rays 5, Yankees 3

Hours before the Rays completed the sweep of the Yankees and dropped the Bombers to an even .500 on the season, Ken Rosenthal broke the news that Miller had been dealt to Cleveland. The return package was highlighted by Clint Frazier, a former fifth overall pick, and Justus Sheffield, a top-100 prospect. After three straight losses and dwindling playoff odds, it was the right move, but it still was difficult to grasp in real time that the New York Yankees had seemingly bowed out of the playoff race to secure a brighter long-term future.

“I remember there was surprise around the industry and that they took that step, because nobody had ever seen it,” Olney said. “I remember early in the year and in early July that there were columns saying ‘Hey, what are we doing here, the Yankees always go for it.’ I remember some folks were writing along those lines, and maybe because they were conditioned by George [Steinbrenner] all of those years.”

But George’s son Hal had heard Cashman’s plea, and the sales were on. Had the Yankees gone into all-out sell mode? Just ask Seth Berkman, who wrote this in the New York Times shortly before the trade deadline: “The true signal that the Yankees are ready to abandon this season to build for the future would come by trading the team’s best hitter, Carlos Beltran.”

Well, that came a day after the sweep at the Trop, as the yankees sent Beltran to the Rangers, and Ivan Nova to the Pirates shortly after. Nearly every tradable asset was moved, silencing any questions of whether the baseball’s Evil Empire would do the unthinkable and bow out of the playoff race.

“Once Chapman goes, Hal has kind of put his foot in the pool, and once Miller goes, he’s gone into the deep end,” Olney said. “You might as well move all of the assets.”

That’s just what the Yankees did.

“There’s a line all teams must straddle, the line between doing what’s best for winning in the present, and making choices about preparing for the future,” Jack Curry said on the YES Network shortly after the Miller trade. “For the win-now Yankees, it’s even trickier to tip-toe that line, because the Yankees are a win-now team every year. Except this year. This year, the Yankees did something they haven’t done in more than a quarter of a century, when they traded major-league assets for minor leaguers, a concession that it was time to reboot, time to use some of their best players in the present to build a brighter future.”

MLB: AUG 01 Twins at Indians Photo by Frank Jansky/Icon Sportswire via Getty Images

As the fallout from the Yankees’ unprecedented trade deadline unfolded, the question lingered: would history have been different had the Bombers showed up at the Trop, and continued their winning ways rather than falling into a four-game losing skid just before the deadline?

“In baseball especially, as we become rooted in analytics, a small sample size doesn’t really matter anymore,” Olney said. “But that’s the one time of year, like a 10-day period at the end of July where a small sample size can mean everything...that’s the one time where teams just look at it differently, and one win or one loss can convince an owner which direction to go.”

The fateful sweep at the hands of a last-place team changed the course of a franchise. As Gleyber Torres rises to superstardom and other assets from that deadline bring in major-league talent like James Paxton, Yankees fans can embrace the irony that for the most successful franchise in sports history, a crucial turning point in their trajectory came as a result of on-the-field failure.

“The fact that it went as planned, they made great trades and took a big step forward the next year, I think we do look at that time as a pivot point,” Olney said of the 2016 trade deadline. “From that point forward, I think Brian had more buy-in from Hal in terms of executing a more efficient way of looking at players.”

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