- Andrew Marchand, ESPN Senior Writer
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At No. 2 was a New Jersey high schooler named Michael Trout. The Yankees, selecting 29th that year, believed Trout had a chance to fall all the way to the end of the first round.
Yankees general manager Brian Cashman remembers that the team’s vice president of amateur scouting, Damon Oppenheimer, was “infatuated” with Trout.
Oppenheimer said everything just clicked for the Yankees as they judged Trout from Millville Senior High School, where they got a full sense of his skills.
They felt their scouts were more on Trout than other teams, which gave them some hope he would slip to 29. They even had an area scout, Matt Hyde, who personally coached Trout so they had genuine, firsthand knowledge of Trout's attitude.
It was all there for a monumental choice.
Most major league clubs did not value Trout’s potential as much as the Yankees did. The first 24 picks were made and Trout wasn’t one of them. The Yankees, five picks away, watched in their Tampa office draft room, growing a bit more optimistic. Finally, at the 25th pick in the draft, the Los Angeles Angels nabbed Trout and, it appears, landed a future Hall of Famer.
The Yankees’ draft process for Trout was akin to throwing eight shutout innings before seeing your closer blow it in the ninth -- except the final pitches were out of their hands.
That is the exciting, cruel, tension-filled nature of draft day. It can be hopeful and helpless at the same time, with the ability to transform scouts and GMs into legends in their own right, or eventually lead to unemployment.
“It is the biggest day in our sport in terms of the future of it,” Cashman said.
You can do nearly everything right, through years of preparation, and then miss out on Trout and end up with Slade Heathcott at No. 29, a talented but troubled and injury-plagued outfielder who just made his major league debut this year before quickly landing on the DL after six games with a quad injury.
This Monday’s draft contains more intrigue for the Yankees, who own the 16th and 30th selections, than perhaps any other in recent history. No. 16 is the club’s highest pick since 1993, when they took pitcher Matt Drews at 13. Drews never made it to the majors.
For the past two-plus decades, the Yankees have chosen no earlier than 20th except for 2005, when they picked shortstop C.J. Henry at 17.
In the early 1990s, the Yankees had a top-10 pick for three straight years. In 1990, they chose Carl Everett with the 10th pick. Everett had a pretty good career, but is probably best remembered for not believing in dinosaurs.
In 1991, the Yankees selected Brien Taylor with the No. 1 overall pick. Taylor missed out on the team’s dynasty, never throwing a major league pitch after severely damaging his left shoulder in a fight.
In 1992, the Yankees, at No. 6, decided on a high school kid from Kalamazoo, Michigan, named Derek Jeter. Whatever happened to him?
Philosophy and fate
Jeter's fairy tale almost seemed preordained. He grew up dreaming of being the Yankees' shortstop, fell to sixth in the draft and then became the championship-winning captain. But his story, a combination of good fortune and raw skill, is not especially unusual for the draft.
So many tales of teams and players feature more twists, turns and roadblocks than a drive on the Bruckner.
To make it to the Bronx, it takes planning, talent, determination and luck. The draft itself has changed over the years, and now more than ever potential picks are scouted, cross-checked and analyzed in excruciating detail.
The increasing intensity from television and Internet coverage has made an impact, too. Oppenheimer said some opposing scouting directors have told him they take the public reaction to their first choice into consideration. The Yankees say they don't.
Hardened by decades in New York, Cashman fully empowers Oppenheimer to make the selection with one single charge.
“Best player, period,” Cashman said.
With most players needing three to five years to develop, there is no point, Cashman said, in drafting for need. By the time a draftee makes the majors, a club’s past weakness might pivot into a strength.
The draft is not only about who a team wants, but who they don’t want. Executives need to know when to strike and when to fold.
In 2006, Cashman had watched a 6-foot-8 high school right-hander from Grand Street Campus in Brooklyn throw at Yankee Stadium. Cashman grew enamored of the young pitcher's potential. Dellin Betances' stock was high, but perhaps not as high as it should have been.
The way Betances remembers it, his velocity was a little lower in the cold at the beginning of his senior season. By the time the weather and his fastball had heated up, most of the scouts already were gone. Plus, Betances had committed to Vanderbilt, so teams knew his “signability” would be high -- which, in baseball-to-English terms, means he would want a lot of money.
On the day of the draft, while Cashman, Oppenheimer and their staff huddled in Tampa, Betances, his older brother Anthony and some friends were 1,100 miles away in the Coney Island home of Dellin's summer ball coach, Mel Zitter.
The draft was not televised back then, so the group followed it on the Internet. Betances' adviser/agent, Jim Murray, had told Betances he could be a late first-round pick, but he might drop because of his commitment to Vanderbilt.
Beginning in Round 3, Cashman let Oppenheimer know he was eager to grab Betances. Oppenheimer, correctly assessing the landscape, told him they had time.
"Best player, period."
Yankees GM Brian Cashman, on his team's draft-day strategy
In the first round, Oppenheimer chose righties Joba Chamberlain and Ian Kennedy. In the third round, it was righty Zach McAllister. From the fourth through the seventh rounds, Cashman developed a mantra: “Betances. Betances. Betances."
Cashman: “I don’t want to lose this guy.”
Oppenheimer: “He’ll be available later, Cash.”
Meanwhile, in Coney Island, Betances grew a bit weary as name after name appeared on the computer screen, none of them his.
In the eighth round, Cashman got his man. Betances, stung by having to wait so long, was relieved -- he'd been drafted by his favorite team.
Cashman authorized a $1 million signing bonus to entice Betances to skip college. After a long and rocky developmental period, Betances was an All-Star as a rookie in 2014. So far in 2015, he's been even better.
Making a splash
Draftees who have made the majors often have an interesting backstory. In 1998, CC Sabathia was sitting in an art class at Vallejo High School in California, wondering if the end of his baseball career was near.
Before the draft, Sabathia had decided if he wasn’t picked in the first three rounds, he was going to play tight end, accepting a scholarship offer from the University of Hawaii.
Since this was before the draft became a prime-time special, Sabathia waited for word at school. The Cleveland Indians picked Sabathia 20th overall.
“I was sitting in art class and it just came over the loudspeaker,” Sabathia said. “Then I went down to the office and my mom was there. We went back to the house and my whole family was there. We had a barbecue. It was a pretty cool day.”
Later, he spoke with Indians executive Mark Shapiro and asked if he was going to pitch or play first base. Shapiro told him he would be on the mound.
“In my mind, I was a big league hitter,” said Sabathia, although nearly 20 years later, he isn’t so sure he would’ve made it as one.
Jacob Lindgren was drafted last year by the Yankees. But that almost didn't happen. Out of high school in 2011, the Chicago Cubs took Lindgren in the 12th round. When he told them the deal he wanted, the Cubs said they needed to watch him play summer ball first. They watched, but they didn’t make an offer until it was too late.
“I’m moved in at Mississippi State,” said Lindgren, who wouldn’t say how much the Cubs needed to ante up. “I’m having a good time and the day before school starts, they called and they were like, 'We’ll give you bam [they hit my signing bonus number].' It was a tough decision at the time, but I felt I was only going to get better at Mississippi State. It was a good decision.”
Lindgren, a lefty, pitched tremendously as a reliever in college. Oppenheimer and his staff recognized him as a player that could move quickly through their system. The Yankees had the 55th pick in the draft, and Oppenheimer felt Lindgren could still be there.
Lindgren watched the draft on television at a friend’s house. Poolside, he learned the Yankees had selected him.
“Literally, as soon as I got picked, my buddies just launched me in the pool,” Lindgren said.
He made his Bronx debut in May.
Scouting and fate determine the future of a franchise. Sitting at No. 16, the Yankees are in their best position in more than two decades.
ESPN.com draft expert Keith Law predicts the Yankees will take Cornelius Randolph, a 6-foot-1, 200-pound shortstop from Griffin, Georgia. He thinks catcher Chris Betts from Long Beach, California, and second baseman Ian Happ from Cincinnati, also are possibilities.
While no one can know for sure what they will do, the Yankees won’t have to rely as much on chance this year to get the player they want.
“There are more people in the pool,” Oppenheimer said.