The Yankees were out early to stretch prior to the deciding game of the 2001 World Series -- the one where Luis Gonzalez would break their hearts with a soft flare off Mariano Rivera. An 11-year-old boy wearing a replica jersey watched intently from the first row down the right-field line at what is now known as Chase Field, clutching a homemade sign that read, "Yankees Fan Today, Tomorrow, Forever."
Seven years later, the Yanks gave Gerrit Cole an opportunity to wear the pinstripes for real, using the 28th overall selection in the 2008 Draft on the stud right-hander from Orange Lutheran High School in Orange, Calif. Cole's development into a big league star begs the question: What might have been?
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"It's happened more than a few times," said Yankees general manager Brian Cashman. "We had Mark Prior [in 1998] -- we drafted him [in the first round, 43rd overall] and he wound up choosing to go to college instead of starting a pro career here. Like Mark Prior, with Gerrit Cole, there was a signability question -- but one we vetted. We felt comfortable that despite it being difficult, it was something that if we met demands, we could make it happen. In both cases, the signability changed."
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Cole hopped on a conference call with the New York media shortly after the Draft, jovially recalling how he'd had peanuts thrown at him that night in Arizona, and how he and his father had run into Derek Jeter and Paul O'Neill while wandering the lobby at the Yankees' team hotel. Cole expressed hope that his negotiations with the Yanks would go smoothly, though he explained that he needed to sit down with his parents and advisors, weighing a professional contract against his commitment to UCLA.
Despite the college commitment, Yankees officials felt confident that the right offer could sway Cole. Damon Oppenheimer, the Yanks ' vice president of amateur scouting, said that the organization tried to do everything it could to sign Cole, "and do it the right way. That talent level was just too good to pass up."
Of course, no agreement was reached -- in fact, no offer was made, at the family's request. Cole's father, Mark, wanted his son to honor his commitment to UCLA, but it wasn't all about education.
"We did a ton of thinking -- just an absurd amount of thinking about this," Cole once told the Los Angeles Times. "My dad has a Ph.D., and he's a real visual kind of guy, so he made charts, and we went over financial figures, comparing people who are drafted in the first round and have somewhat of a baseball career with others who graduated college and the average gross of what they make in baseball and afterward."

Cole pitched three seasons at UCLA before being taken with the first overall pick of the 2011 Draft by the Pirates, receiving an $8 million signing bonus -- twice what the Yankees were reportedly prepared to offer in 2008.
"You're in competition mode with colleges and the wishes of the parents," Cashman said. "People have the right to change their minds. Going into it, our area scouts felt strongly that the player belongs on the board because of his physical ability, belongs to be drafted there and is signable at the same time. But signability can change even after the Draft. I know UCLA did a full-court press trying to convince Gerrit Cole why the college route was a better alternative at the time than going pro from his high school year."
The Yankees received a compensation pick that they used on outfielder Zachary Heathcott, who played 17 games in the Majors with New York in 2015 and is currently a free agent. Cole reached the Majors in 2013, going 59-42 with a 3.37 ERA in 136 starts for Pittsburgh before being traded to Houston this past offseason. The Yanks seriously discussed Cole with the Pirates, but the Bucs opted for a four-player package from the Astros that included right-hander Joe Musgrove and infielder Colin Moran.

Cashman said that he has no regrets about Cole's saga, though it did sting to see him succeed in other uniforms.
"I just feel like our scouts were right by the talent assessments," Cashman said. "You can't make people do something they don't want to do. Like anything else in life, you have decisions; you come to a fork in the road, you go left or you go right. Unfortunately, in some of these players' particular cases, they chose to go in a different direction. We didn't benefit from being right on the talent, but you get back at it.
"I have a great amateur scouting department run by Damon Oppenheimer, with tremendous scouts that work their tail off. They didn't let that stuff detour them; they stayed at it and found other guys that ultimately wanted to be Yankees and have produced for us."