In the shadow of Medinah Country Club’s majestic clubhouse, at a PGA Championship long ago, Ben Crenshaw waited for his audience with the boy king. Crenshaw was a month away from serving as captain of the 1999 U.S. Ryder Cup team, so he was closely eyeing the final round of the PGA, watching to see how both teams might gel. Just moments earlier, Sergio Garcia had run out of holes in a thrilling duel with Tiger Woods, failing to claim the Wanamaker trophy but securing a spot in his very first Ryder Cup. “Boy, that kid is gonna be a handful,” Crenshaw said. Finally, the young Spaniard materialized, and Crenshaw offered him a manly hug and some down-home consolation: “You didn’t get this one, but you’re gonna win so many of these you’re gonna get tired of lifting trophies.”

Of course, who didn’t get swept up in the turn-of-the-century Sergiomania? The kid had it all, including a boyishness that transcended borders. But what Crenshaw couldn’t know was that the “99 PGA Championship would propel Woods to the most dominant run of golf ever played. Poor Sergio had his spirit crushed along the way, and by the time the 2002 U.S. Open rolled around, his public image had already curdled, culminating in him flipping the bird to a Bethpage gallery that was mercilessly heckling him. (Sometimes the jeers turned into mockery, as when Sergio showed up for the final round of the 2006 Open Championship, and another showdown with Woods, in an all-yellow outfit. Overserved fans took to calling him both “Big Bird” and “Banana Man.”) Over the next decade and a half, Garcia did indeed manage to lift many trophies, but of course no majors. He had good health, immense wealth and a string of glamorous girlfriends, and yet he somehow became a tragic figure—what the British tabloids liked to call a “nearly man.”