3 Biggest Prospect Letdowns in Yankees History

The New York Yankees are the model organization in Major League Baseball. Push aside their free agency spending, and look at the prospects they've called up from their farm system. Derek Jeter, Andy Pettitte, Mariano Rivera, and Jorge Posada all say hello. Yet the Yankees have been prone to putting too much faith in prospects who never lived up to their scouting reports, just like every other less successful team in the game.

When thinking of the biggest prospect letdowns in Yankees history, these three stand out above the rest.

3. Ruben Rivera

Back in 1990, the Yankees signed outfielder Ruben Rivera as a free agent out of Panama. The cousin of Hall of Fame closer Mariano Rivera impressed scouts with his speed and power, as he slashed .273/.417/.371 in the Gulf Coast League in 1992. His numbers only got higher once he climbed up the minor league ladder until he finally received his major league call up in 1995, yet his behavior turned off the Yankees. Rivera didn't take being sent down to the minors in 1996 too well. He did put up decent numbers (.281 batting average, .816 OPS, two homers and 16 RBI) through his two years with the Yankees, but was traded to the San Diego Padres in 1997. Rivera would return to New York in 2002, but was cut after allegedly stealing Derek Jeter's glove and selling it to a memorabilia dealer for $2,500. Rivera left the organization and fan base wanting more. At least Mariano worked out well!

2. Jesus Montero

Jesus Montero was supposed to be the heir apparent to Jorge Posada. He was signed by the Yankees as an international free agent in 2006, and was dubbed the best power hitter in the entire class. Montero lit it up throughout his four years in the minor leagues until he finally received his promotion in 2011. Montero lived up to his batting potential, as evidenced by his .328 batting average and .996 OPS in his 18 games in pinstripes. However, his main issue was his defense behind home plate. At the end of the season, the Yankees traded Montero to the Seattle Mariners in a package deal for starting pitcher Michael Pineda. Yankee fans were riled up that they would trade the supposed phenom, but they calmed down after seeing his production drop throughout his four seasons with the Mariners. His MLB highlight? Getting an ice cream sandwich thrown at him by an M's scout.

1. Brien Taylor

It's been 19 years since the Yankees selected high school pitcher Brien Taylor with the first overall pick of the 1991 MLB Draft. Taylor immediately cashed in on a $1.55 million contract with New York, thanks to super agent Scott Boras. In his first two seasons in the minors, Taylor struck out 327 batters in 324 innings, and registered a 19-15 record. At the conclusion of his second year, Taylor tore his rotator cuff completely off the bone while defending his brother in a bar fight. He was never the same once returning to the mound in 1995, and eventually retired in 2000 without ever reaching the major leagues. Oh what could've been if Taylor had never been inside that bar.