New York Yankees: A look back at some of the best prospects of the last 30 years and how they fared

New York Yankees, Derek Jeter
Sep 28, 2014; Boston, MA, USA; New York Yankees shortstop Derek Jeter (2) waves to the crowd after being replaced by a pinch runner during the third inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports

Baseball America has issued its top 10 prospects for the 2022 season. The New York Yankees have three top prospects on that list. Shortstop Anthony Volpe at number 10, Shortstop Oswald Peraza at number 55, and Outfielder Jasson Dominguez at number 87. Looking back over the last thirty years, the Yankees have had some amazing talent that went on to be tremendous stars for the Yankees and some that were absolute busts.

Today we look back on several past top prospects and how they fared in their careers in no particular order. Obviously, there are dozens more that are not covered in this article, but these are some of interest.

  1. Anthony Volpe – Minor League Stats: .276/406/548 .954 OPS, with 29 home runs and 97 RBIs. It is probably too early to put him on this list, but he is one of the best prospects the Yankees have had in years. He has power at the plate and is an above defender at shortstop. He is included in this list as he is current and of the most interest to present-day Yankee fans. Baseball America has named him the number 10 prospect on the list for 2022.
  2. Bernie Williams – Career Stats: 297/.381/.477, .858 OPS, 287 HR, 1,257 RBI, 147 SB. His highest Baseball America ranking was 11. Williams was an excellent center fielder for the Yankees, he was part of the dynasty years with Derek Jeter, Mariano Rivera, Andy Pettitte, and Jorge Posada, who reigned supreme. He was a contributing part of four World Series titles and was a Silver Slugger, a four-time Gold Glover, and a four-time All-Star. He was definitely one of the best Yankee prospects ever.
  3. Drew Henson – Career Stats: .111/.111/.111, .222OPS, 0HR, 0RBI, 0SB. Highest ranking 9. Henson was drafted in the third round of the 1998 draft. Henson was one of the biggest highly-rated prospects to be an absolute bust for the Yankees. He was traded away and traded back to the Yankees. He never really got to prove himself as he retired and went to the NFL.
  4. Jose Contreras -Career Stats: 1154.1 IP, 77-67, 3.86 ERA, 1.36 WHIP, 869 K, 418 BB. Highest rating 6. His claim o fame was a one-time World Series Champ and a one-time All-Star. He was with the Yankees for a season and a half. The Cuban defector never lived up to the hype when the Yankees acquired him in 2002. Although having a decent career. He was traded to the Chicago White Sox.
  5. Nick Johnson – Career Stats: .270/.401/.443, .844 OPS, 91 HR, 387 RBI, 27 SB. Highest rating 5. Johnson had a decent season in 2003 but was traded in 2004. He returned to the Yankees in 2010 for one season. He had lofty expectations that he never realized.
  6. Derek Jeter -Career Stats: .310/.383/.449, .832 OPS, 260 HR, 1311 RBI, 358 SB. Highest rating 4. Derek Jeter was one of the best players to ever play the game of baseball he spent all 20 years of his career with the Yankees. He was a five-time World Series Champion, five-time Gold Glove, four-time Silver Slugger, two-time Hank Aaron Award, one-time All-Star MVP, one-time World Series MVP, Rookie of the Year, 3,000-Hit Club while being a twelve-time All-Star. He was a top shortstop and was enshrined in the Baseball Hall of Fame in 2021.
  7. Phil Hughes – Career Stats: 443.2 IP, 36-23, 4.46 ERA, 1.30 WHIP, 370 K, 157 BB. Highest ranking 4. Hughes being moved back in forth from a starter to a reliever and back never really lived up to the hype he was surrounded with in 2007 when the Yankees hired him. Hughes ended up being traded to the Twins. His 2010 year was his best with 18 wins and being a one-time All-Star. After four mediocre years with the Twins, he was traded to the San Diego Padres. He retired from baseball in 2018.
  8. Aaron Judge – Career Stats: – .276/.386/.584/.940. To date, he has 158 home runs and 366 RBIs. Big raw power from 6-7 frame but has solid hitting/OBP skills to go with it, profiles as classic power-hitting right fielder. It’s hard to determine how his career will turn out, as he has been riddled with injuries in three of his five years with the Yankees. At age 29, he had one of his best years at the plate, hitting .287. He was Rookie of the Year in 2017.
  9. Greg Bird – Career Minor League Stats: .271/.376/.472. He had 14 homers, 63 walks, 97 strikeouts in 369 bats in High and Double-A. Good power and prowess at the plate in the minors. He looked like a top prospect in He was not a great athlete and was highly prone to injury in the majors. His big plus is that he was a switch hitter, very Nick Swisher-like. After four years with the Yankees and attaining a major league career batting average of just .211, he retired from baseball. He was surely a flop for the Yankees. 
  10. Joba Chamberlain – Career Stats: 382IP, 20-13, 65 HLD, 3.70 ERA, 1.34 WHIP, 386 K, 150 BB. Highest ranking 3. One-time World Series champ in 2009. He may not have been handled correctly by the Yankees as he shuffled back and forth from starter to reliever. Unfortunately, he tore a UCL and underwent Tommy John surgery, He never reached his potential with the Yankees, although he went on to play for the Tigers, Royals, and the Indians. He mostly failed with all three teams and retired from baseball after just ten years.’s Columnist William Parlee is a member of the Society for American Baseball Research. Follow me on Twitter @parleewilliam.