Andy Pettitte was a later-round draft pick that thrived, rising from the 22nd round of the 1990 June Amateur Draft to become a stalwart in the New York rotation for the better part of two decades.
Pettitte was selected as an 18-year-old and the left-handed Texan reached the majors in 1995, joining the rotation early in the season and finishing third in the Rookie of the Year voting that season.
In 1996, Pettitte emerged as an ace, leading the American League with 21 wins and finishing second in the Cy Young voting.
He would win 20 games once more in his career, in 2003, but was a solid piece of the rotation for four World Series championships from 1996-2000.
Pettitte left as a free agent in December 2003 to sign with the Houston Astros, but returned three years later and helped pitch New York to another World Series title in 2009.
He retired in February 2011, but returned to the Yankees a third time the following spring, pitching two more seasons before retiring for good at the end of the 2013 season.
He was a three-time All-Star and led the American League in 1997 by allowing only 0.3 home runs per nine innings, a remarkable feat in the era in which he played.
His tenure in New York was not, however, without controversy. In 2007, Pettitte admitted to using human growth hormone while recovering from a 2002 elbow injury.
Pettitte was one of 85 players named in the infamous Mitchell Report following an investigation into performance-enhancing drug use in baseball.
In 15 seasons with the Yankees, Pettitte was 219-127 with a 3.94 ERA (115 ERA+) and 1.373 WHIP, notching 2,020 strikeouts in 2,796.1 innings.
Pettitte appeared in 13 postseasons with New York, making 40 starts and going 18-10 with a 3.76 ERA and 1.305 WHIP over 251.1 innings. He was the MVP of the Yankees’ 2001 ALCS win over the Seattle Mariners.