1. Drew Henson

Drew Henson is number one for two reasons: he failed on both the Yankees and the Dallas Cowboys. Being two of America’s most popular teams, I’m surprised he didn’t try out for the Los Angeles Lakers yet.

On a more serious note, Henson chose baseball over football when he was selected in the third round of the 1998 MLB draft. He showed a lot of promise, especially as a third baseman and the Yankees had high hopes that he would be the third baseman of the future.

With a lackluster performance in his first year of playing, Henson was traded away to the Cincinnati Reds, only to be brought back to the Yankees for Wily Mo Pena. His return only cemented his future (or lack thereof) in the Bronx. He struggled mightily in Triple-A.

Henson eventually found his way to the major leagues, even if it was only for eight games over two seasons. When he wasn’t considered as a replacement for third base once Aaron Boone suffered a knee injury, Henson wanted out of the Bronx.

Given the chance of a lifetime, Henson did not live up to his potential and, eventually, threw it all away. Even his time with the Cowboys wasn’t promising.

So as we are praising these Yankees prospects today, we can’t forget about what has happened in the past. They may all grow up to be superstars in the Bronx but there’s always a chance there could be some Drew Henson’s in the mix.