Since they don't believe in rebuilding years, the New York Yankees have had a tendency to trade away top draft picks in their desire to win immediately. Because the Yankees have more financial resources than any other team in baseball, they generally rely more of signing free agents . New York has not had a first-round draft pick make it big with the club since it drafted a shortstop out of Kalamazoo, Michigan by the name of Derek Jeter in 1992.

Similarly, the Yankees have not had a successful starting pitcher come out of their system since Andy Pettitte was chosen by New York in the 20th round in 1990. Robinson Cano , who has developed into one of the game's top second baseman, is the first star position player developed by the Yankees since Jeter. Designated hitter Nick Johnson , who was re-aquired by the Yankees in the offseason, was New York's first-round pick in 1996.

However, Johnson was frequently injured during his first stint with the Yankees and was traded to the Montreal Expos in 2003. Outfielder Brett Gardner , expected to start in either left' or center field in 2010, was taken by the Yankees in the third round of the 2005 draft. However, Gardner did not play on an every basis in 2009, his first full season in the majors.

Young pitchers Joba Chamberlain and [Phil Hughes]], who began spring training in a battle for the No. 5 spot in the Yankees' rotation, are products of New York's system. Chamberlain was taken in the second round of the 2006 draft and Hughes was chosen in the first round in 2004 as an 18-year-old out of high school.

In 1990, then baseball baseball commissioner Fay Vincent suspended Yankees owner George Steinbrenner for life after he paid Howie Spira , a small-time gambler, $40,000 to spy on outfielder Dave Winfield . However, Steinbrenner was reinstated after he threatened to sue. Gene Michael , the Yankees' general manager in the early 1990s, turned out to be the architect of the Yankees' teams that won four World Series titles in five years from 1996-2000.

Michael drafted the nucleus of those championship teams. In addition to Jeter and Pettitte, closer Mariano Rivera signed with the Yankees as an undrafted free agent in 1990, the same year catcher Jorge Posada was drafted in the 20th round. Jeter, Pettitte, Rivera and Posada became known as the "Core Four" because they are the only players who have been on all five of the Yankees' World Series- winning teams since 1996.

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