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NOBODY COULD believe what Gary Sánchez was doing late last summer, least of all Gary Sánchez. After every one of the 20 home runs he launched in a span of just 48 August and September games, the 23-year-old rookie catcher returned to the Yankees' bench for a few deep, incredulous breaths. Is it really me who's doing this? he would ask himself. My god, is it really me?

It was. Although he had participated in just one big league game over the season's first four months, Sánchez's historic, mesmerizing streak—he reached 19 homers faster than any rookie in baseball history—propelled him to a second-place finish in the AL Rookie of the Year voting. It also spurred rivals around baseball to ask themselves: My god, are these really the Yankees?

By the time Sánchez arrived they looked little like their usual collection of high-priced mercenaries. As early as June, with New York floating around .500, Brian Cashman had begun suggesting to the club's rebuilding-averse ownership that he might want to assume a role he had never taken on in his first 18 years as general manager: trade-deadline seller. By Aug. 12, with owner Hal Steinbrenner's approval, Cashman had not only dealt outfielder Carlos Beltrán and relief aces Aroldis Chapman and Andrew Miller for prospects, but he had also given Alex Rodriguez a respectful, if involuntary, early retirement. Two days later, with playing time now available, Sánchez slugged his second homer of the season, the start of a streak announcing that the Yankees' future had arrived. By September, the Yankees' youth contingent also included outfielder Aaron Judge, first baseman Tyler Austin and pitchers Luis Cessa and Chad Green.

To Cashman, the future looked a lot like the past. Few teams—and few institutions—fetishize their history quite like the Yankees. But for years a pastiche of pinstripes, monuments and scalloped arches has masked the club's disconnection from its greatest legacy: winning. While the Yankees haven't finished below .500 since 1992—the year Cashman, at 25, became assistant GM—they haven't had a playoff victory since '12, despite continuing to spend more than any other club except, recently, the Dodgers. "Most teams don't back a truck up and buy a world championship," Cashman says.

It appeared to many as if he had done just that in 2009, after a winter in which New York dropped $423.5 million on free agents A.J. Burnett, CC Sabathia and Mark Teixeira was followed by a 27th title. But the heart of the team was still largely the same as it had been for 1996's number 23, and for numbers 24, 25 and 26, which came during Cashman's first three years as GM, starting in '98: Derek Jeter, Andy Pettitte, Jorge Posada and Mariano Rivera, players who came up through the Yankees' system.

Cashman's 2016 deadline dealings brought back three prospects who appear on Baseball America's new top 100 list: shortstop Gleyber Torres (No. 5), outfielder Clint Frazier (No. 39) and pitcher Justus Sheffield (No. 91). In reality, though, Cashman had been preparing to change direction for a while. That new trio joined four other top 100 prospects (outfielders Judge and Blake Rutherford, shortstop Jorge Mateo and righthanded pitcher James Kaprielian) to give the Yankees the consensus No. 2 farm system in baseball, after the Braves.

The result is that no team other than the Cubs seems better positioned to (eventually, anyway) string together a run of dominance like the Yankees' of 20 years ago, nor to more effectively take advantage of what promises to be history's greatest free-agent class two years from now, one that might include Bryce Harper, Clayton Kershaw, Manny Machado and Josh Donaldson.

One position at which they appear set for the long term is catcher. Sánchez seemed an overnight sensation late last summer, but he wasn't at all. Back in February 2009, Cashman flew down to the team's facility in Boca Chica, D.R., to watch a workout by the 15-year-old his scouts kept raving about. Though Sánchez wasn't far removed from the days when he and his brother had been in the streets hitting dolls' heads with broomsticks, Cashman agreed with his scouts: "I told my guys, 'Listen, we have to do whatever it takes to get this guy to say yes to the Yanks.'" It took $3 million.

The next five years brought challenges that would overwhelm most teenagers, even rich ones. Sánchez had to learn how to be a professional; how to live in a new country; how to speak a new language (he still uses a translator with the media, though not with his pitchers); how to properly play the sport's most demanding position. For a while it seemed as if he might never rise above Double A Trenton (N.J.), where he spent parts of three consecutive seasons. "Yeah, I got tired of Trenton," he says.

The birth of his daughter, Sarah, in 2014, kicked him into gear. "As a father, you want the best for your kid," he says. This winter was the first, though, in which he found himself stopped by fans wherever he went in New York and the Dominican. "Are you Gary Sánchez?" they asked. He couldn't fib if he wanted to: On his left forearm, stretching nearly from wrist to elbow, is a tattoo that reads SÁNCHEZ in green and blue. "Maybe if I wear long sleeves, I could get away with it," he jokes. Hardly. All they need now is a glimpse of his face—the face of a new Yankees era.