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  Promoted to assistant GM late in 1992, Cashman became the second-youngest general manager in baseball history in February 1998, taking the reins of the Yankees following Bob Watson’s resignation. Then thirty years old, Cashman was the sixteenth GM to hold the office under Steinbrenner, and never dreamed he’d be the last. Uncertain if he wanted the position long-term, Cashman told Steinbrenner that he would operate through his first year on a handshake agreement.

  “My attitude at the time was, I don’t want the Yankees tied into something if they don’t know if it is going to work or not,” Cashman said. “I was smart enough to realize this is too great of an opportunity to turn down, but I understood this job is so much more important than yourself.”

  When Joe Torre’s team started the season with four losses in its first five games, Steinbrenner panicked and placed a call to Gene Michael, who’d served as the Yankees’ GM from 1990–1995 and was settling into a role as the team’s director of major league scouting. Steinbrenner told Michael that a mistake had been made and that he should return to his old office, taking over for Cashman.

  Michael stalled for time, assuring Steinbrenner that Cashman would be capable of handling the job if given a chance. The 1998 Yankees proved to be a powerhouse team, going on to set an American League record with 114 wins (later surpassed by the 2001 Mariners, who won 116 games) and sweeping the Padres in the World Series. Cashman received a legitimate contract following that season, eventually becoming the longest-serving Yankees GM since Ed Barrow led the team from October 1920 through February 1945.

  “This would be nothing I ever would have thought was possible, in any shape or form,” Cashman said. “The general manager I happen to be today is radically different than the one that started this job. Experience has served me well, but it doesn’t hold me back in recognizing that I don’t have all the answers. I don’t ever have this job figured out.”

  Given his damn-the-torpedoes education in the Yankees family, Cashman could have been tempted to overlook the red flags popping up as his team approached the midway point of the 2016 season. Six years after The Boss’ passing, “rebuilding” remained a dirty word in the offices, and few would have faulted Cashman if he wanted to pitch the idea that the aging roster could capture some magic and sneak into the playoffs.

  It would have been a message that played well upstairs at Yankee Stadium and on the fourth floor of the Tampa facility that now bore Steinbrenner’s name, where Hal Steinbrenner—a self-described “finance geek”—spent many of his hours poring over forward-looking spreadsheets. Perhaps they could add to the roster; Cashman had enjoyed a fair amount of success when approaching ownership with requests to add salary, despite his current boss’ oft-repeated statement that a chance to win a title should not require more than $200 million.

  Yet as Cashman surveyed the roster that bore his fingerprints, he could not convince himself that it was a team capable of great things. For example, their offense had been built around the expectation that Alex Rodriguez and Mark Teixeira would combine for 60 homers and 200 RBIs; the tandem would manage 24 homers and 75 RBIs that season. In what Cashman would later characterize as a series of the most difficult conversations that he had ever presented to ownership, the GM was forced to explain to Steinbrenner why his team wasn’t good enough to win the 2016 World Series.

  That was the bad news. The good was delivered as Cashman detailed to Steinbrenner how he envisioned re-establishing the Yankees as a “super team,” with this seeming to be a prime opportunity to accelerate that process. Cashman’s recommendation was to flip some of the Yankees’ better-known assets in order to replenish the farm system for 2017 and beyond. If executed properly, that tactic would accentuate the youth movement that had already delivered Luis Severino and Greg Bird (when healthy) to New York. It was the only viable route; Steinbrenner would never authorize an outright rebuild like the Astros and Cubs had recently endured.

  “The easy thing is to see that cliff and recommend, ‘Let’s just drive off the cliff,’” Cashman said. “Then, all of a sudden, you’re in that tanking mode and you’re not straddling that halfway mark where you’re rebuilding and trying to compete at the same time. That could bring you to the middle of the pack.”

  The Yankees were in Houston when the first domino fell, with Cashman agreeing to ship left-handed closer Aroldis Chapman to the Cubs in exchange for a four player package that included nineteen-year-old Venezuelan infielder Gleyber Torres, who was rated as Chicago’s top prospect. Cashman referred to Torres as “the equivalent of a firstborn,” and the move would have been recognizable to any Wall Street insider as a classic turnaround flip.

  When the Yankees acquired Gleyber Torres from the Cubs in July 2016, general manager Brian Cashman referred to the standout infielder as “the equivalent of a firstborn.” (© Laura Nawrocik)

  Chapman had been what Cashman called “an asset in distress” when the Yankees acquired him on the cheap from the Reds prior to the season, facing what would be a thirty-game suspension under Major League Baseball’s domestic violence policy. A trade that would have sent Chapman to the Dodgers during the 2015 Winter Meetings was called off when reports surfaced that he and his girlfriend had been involved in an October disturbance during which Chapman allegedly fired eight gunshots toward a garage wall.

  Police were dispatched to the pitcher’s home in Davie, Florida, and though Chapman was not arrested and no criminal charges were filed, the optics of the incident were enough to scare the Dodgers off. Cashman and Steinbrenner spoke at length about the delicate situation. Chapman was the hardest thrower in history, regularly exceeding 100 mph with his fastball, and had been an All-Star during his final season in Cincinnati. The Yankees fully expected that the league would discipline Chapman for his actions, but they also believed it wouldn’t be a season-long suspension and that he would pitch somewhere in 2016. It might as well be for them.

  The Reds told Cashman that they were now willing to make a deal without obtaining any of the Yanks’ untouchables, and so three days after Christmas, a trade was consummated in which Chapman went to New York for four mid-level prospects: right-hander Caleb Cotham, right-hander Rookie Davis, third baseman Eric Jagielo (who’d been selected twenty-sixth overall in 2013, ahead of Aaron Judge at thirty-two), and second baseman Tony Renda. In his remarks following the trade, Cashman said he recognized that because of the ongoing circumstances, “The price point on acquisition has been modified.”

  That deal had created a three-headed bullpen monster of Dellin Betances, Andrew Miller, and Chapman, and now Cashman saw a chance to cash in on Chapman’s restored value, two months before Chapman would be eligible for free agency. Smartly tagged “No Runs DMC,” the trio had been as good as advertised: the Yanks were 19-2 when Betances, Chapman, and Miller all pitched, combining for a 1.36 ERA and 13.70 strikeouts per nine innings in those games.

  Cashman said that the thought of flipping Chapman for prospects had been part of those initial conversations with Steinbrenner prior to the trade with the Reds.

  “If it played out well enough with all aspects of the club, then we’d see where it would take us,” Cashman said. “If it did not, we knew we would be in a situation where, as long as he stayed healthy and performed to his norms, there would be potential upside on someone that was going to be a free agent in almost two months. We decided to maximize that value.”

  In addition to Torres, the Yankees re-acquired right-hander Adam Warren, who had been traded to the Cubs in the Starlin Castro deal, plus minor league outfielders Billy McKinney and Rashad Crawford. Cashman said that it had been “an easy call, and the right call” to move Chapman because the Yankees were able to trade from an area of strength to complete the transaction.

  Theo Epstein, the Cubs’ president of baseball operations, said that the Yankees’ insistence on receiving big league-ready starting pitching forced the teams to work on a more creative package. Warren’s inclusion helped to convince Steinbrenner to offer his stam
p of approval, as his impact on the big-league roster would be immediate, not years down the line.

  “This isn’t a white flag,” Cashman said. “This is a rearrangement.”

  Cashman said that the Yankees had maintained strong interest in Torres since 2013, when they viewed the Caracas, Venezuela, native as the top international free agent available. Born less than two months after third baseman Charlie Hayes squeezed the final out of the 1996 World Series, Torres instead signed with the Cubs, from whom he scored a $1.7 million signing bonus and quickly established himself as one of the brightest prospects in the sport.

  McKinney was a toolsy left-handed hitter from Plano, Texas, who had emerged from high school to become the twenty-fourth overall pick in the 2013 draft, hearing his name called by the Athletics. Cashman said that the Yankees had intended to select McKinney if he fell to them at twenty-six, and they watched closely when McKinney landed with the Cubs a year later as part of Chicago’s return for a trade involving pitchers Jeff Samardzija and Jason Hammel. Cashman referred to Crawford, a raw lefty-swinging outfielder from Atlanta, as “a lottery ticket.”

  “The total package was something that we targeted and strived to get, and if we got it, we would move toward a recommendation,” Cashman said. “I made the recommendation to ownership that they thought on, and they gave the sign of the cross to it.”

  Steinbrenner instructed Cashman to continue assessing market values, both coming and going. Cashman reported to Steinbrenner, team president Randy Levine, and chief operating officer Lonn Trost that it seemed to be a “very volatile time” throughout the baseball landscape. The addition of a second Wild Card was partially responsible for that, making it more difficult for teams to honestly assess if they should consider themselves contenders or pretenders.

  • • •

  The clock at Tropicana Field read 8:57 p.m. ET on the evening of July 30, when Rays closer Alex Colome zipped a 94.8-mph fastball past Starlin Castro for the final out of a 6–3 Yankees loss, their third straight. The Yankees were now a game over .500 at 52-51, in fourth place, and 6½ games behind the division-leading Blue Jays. Having been among the 25,883 in attendance at the dimly-lit Trop, Steinbrenner crossed the Howard Frankland Bridge toward Tampa and decided that he had seen enough.

  Shortly before midnight, Steinbrenner told Cashman that he was free to trigger more trades. Cashman was reminded that it was not in ownership’s DNA to permit a strategic tank job, recalling his marching orders to walk the fine line between rebuilding and contending, “but not to fall off.” Cashman and his lieutenants worked their sources in the overnight hours, eschewing sleep in favor of encouraging opposing clubs to ask about everyone and anyone on the roster.

  “Any business entity or corporation needs to be honest with itself,” Cashman said. “If you’re going to change course, you can double down or triple down like a guy who’s losing his shirt at the poker table and try to win it all back, or you have an honest assessment and say it’s time to change course. If it’s a poker player, it means folding up your tent and walking away because I don’t want to lose anymore, or it’s we need to plot a new course and do it fast because things can get much worse if you don’t.”

  The Yankees had not acted as midseason sellers since their dismal 1989 season, when they traded future Hall of Famer Rickey Henderson to the Athletics for pitchers Greg Cadaret and Eric Plunk, plus outfielder Luis Polonia. Suffice it to say that these opportunities did not come around very often in the Bronx, and so Cashman was intent upon securing both quality and quantity.

  “The Yankees have acted a certain way for a long time, and trying to change course from that was difficult,” Cashman said. “But at the same time, it’s continuing to remind everybody that the chess board that we’re playing is way different than the one their dad was playing. They have limitations on the international amateur space, they have limitations in the domestic amateur space, they have penalties on winning, and a significant portion now is the luxury tax and revenue sharing. There are a lot of different things dragging you under that are preventing us from being all we can possibly be.”

  On the morning of July 31, Andrew Miller reached for his buzzing cell phone, expecting to see an alarm going off. Instead, Cashman’s name popped up on the caller ID, and Miller realized that his final pitch as a Yankee had been thrown. Miller was informed that he had been traded to Cleveland for a four player haul of outfielder Clint Frazier, left-handed starter Justus Sheffield, and right-handed relievers J.P. Feyereisen and Ben Heller.

  Indians president Chris Antonetti described the talks for Miller as having been “excruciating,” but the Yankees knew there was great value baked into the player, given that his team-friendly contract offered Cleveland control for two more seasons after 2016.

  “I think most trade talks are excruciating. Most don’t go anywhere,” Cashman said. “The more interesting dynamic in the Miller discussions were negotiations with ownership, simultaneously with opposing clubs. Even if I got satisfied from an opposing team standpoint like we did with Cleveland, there was no guarantee that ownership would relinquish the short-term for a longer view. It was a lot of heavy lifting I was going through, from all ends.”

  A tall, personable southpaw with one of the game’s most lethal sliders, Miller had bypassed asking for a no-trade clause in his four-year, $36 million Yankees contract. That occurred in part because the Tampa resident loved having spring training near his home, which allowed him an extra two months of the year in his own bed. Unfortunately for Miller, the Indians hold their spring camp in Goodyear, Arizona.

  “I was focused on being a Yankee,” Miller said. “The important thing was being part of a winning team. I made a lot of good friends; I miss those guys in New York. They were great teammates, it was a great team to play for, it was a great city to live in. But I’ve got a chance to be a part of a team that’s going to the World Series, and you couldn’t ask for anything better.”

  In surveying the Indians’ assets, the Yankees had refused to be moved off of Frazier, an energetic twenty-two-year-old outfielder nicknamed “Red Thunder” whom Cashman said “shows up for the National Anthem in a dirty uniform.” During that same conversation, Cashman lauded Frazier’s bat speed as being “already legendary,” and that skill promised to carry the right-handed swinger all the way to the majors from his modest upbringing in Loganville, Georgia.

  Having moved from third base to the outfield prior to his junior year, Frazier was the first high school position player taken in the 2013 draft, going fifth overall to Cleveland. Frazier received a $3.5 million signing bonus to bypass his commitment to the University of Georgia, which was the largest bonus that the Indians had doled out at the time.

  The cash influx was desperately needed. Frazier’s father, Mark, was a building supplies salesman who had been laid off twice and was struggling to keep up with the mortgage of their home. With a few dashes of a pen, those problems were erased; Frazier insisted upon using his bonus for that purpose, a gesture that prompted tears of joy from his mother, Kim. For good measure, Frazier gifted his father a new Dodge pickup the next Christmas.

  Ten days after the draft, the reigning Gatorade National Baseball Player of the Year was invited to take batting practice at Progressive Field. The Indians’ big-league roster celebrated the occasion by wearing bright red wigs, a nod to the distinctive red curls that flowed out of the back of Frazier’s batting helmet as he slugged a school record of 63 homers at Loganville High.

  Frazier thought the goof had been “awesome,” as were the long conversations he enjoyed that day with Indians manager Terry Francona and veteran Jason Giambi, with whom he played video games before exchanging cell phone numbers. Soon, Frazier was boarding a jet to take his first professional at-bats with the Indians’ rookie-level club in Arizona, fulfilling a dream that he had identified while most of his classmates were busy finger painting and learning the alphabet.

  “It’s what I always wanted to do,” Frazier said. �
�My mom still has a picture that I drew in kindergarten that she saved and put away in a scrapbook. We had to draw what we wanted to be when we grew up, and I drew a baseball player.”

  Cashman personally reached Frazier on the day of his trade, welcoming him to the organization and informing Frazier that he should report to the Yankees’ Triple-A affiliate.

  “I remember having the conversation with Brian Cashman,” Frazier said. “One of the first questions I asked him was, ‘Do I have to cut my hair?’ And I did.”

  Left unsaid during that call was that the Yankees believed Frazier had been aggressively promoted to Triple-A by the Indians; at twenty-one, he was more than five years younger than the average player at that level. Cashman thought that Frazier probably should have spent the entire 2016 season in Double-A, but ultimately the GM decided that adding a demotion to the trade would over-complicate the situation.

  Cashman had more work to do as the minutes ticked off to 4:00 p.m. ET on August 1, with the trade deadline pushed a day from its usual July 31 place on the calendar. Though trades could still be completed after that date, all involved players must pass through waivers, providing opponents with an opportunity to block the moves.

  It was a risky game within the game. In August 2000, the Yankees placed a claim on the Devil Rays’ Jose Canseco, intending to keep the aging slugger from impacting the division race. To Cashman’s surprise, Tampa Bay gave Canseco’s contract to the Yankees, gratis. A spare part that Joe Torre never seemed sure how to use, Canseco appeared in thirty-eight games for Yankees, including a pinch-hit appearance in Game 4 of the World Series. He struck out looking.

  Chapman and Miller were now gone, and as the Yankees shopped the rest of their wares, Cashman bluntly labeled his team as a “playoff pretender.” Carlos Beltran and Ivan Nova soon became former Yankees, on their way to join the Rangers and Pirates, respectively. A well-respected switch-hitter from Puerto Rico with a promising Cooperstown case, Beltran netted a three player package of pitchers Nick Green, Dillon Tate, and Erik Swanson, with the Yankees kicking in approximately $3.7 million to offset the thirty-nine-year-old’s remaining salary.