New York Yankees head scout opens up on 'gut-wrenching' Mike Trout opportunity in 2009

In 2009, the New York Yankees came agonizingly close to drafting arguably one of the greatest players of this generation, Mike Trout, and it remains one of the biggest 'what-ifs' in MLB history. The New York Yankees are one of the most storied franchises in Major League Baseball, with a long history of success and a reputation for fielding some of the greatest players in the game. However, even the most successful teams have missed out on potential superstars, and the Yankees are no exception.

Trout, who was born and raised in New Jersey, was a highly-touted prospect coming out of high school in 2009. The Yankees had their eye on him, and their head scout, Damon Oppenheimer, scouted Trout extensively and was convinced of his potential. However, the Yankees lost their chance after the Angels selected him, using their compensation pick from the Yankees who ended up drafting outfielder Slade Heathcott.

That change of direction didn't work out as planned. Heathcott had a solid career in the minors but never made much of an impact in the majors. Meanwhile, Trout went on to win two American League MVP awards in his first five seasons in the league, establishing himself as a future Hall of Famer.

It's a decision that still haunts Oppenheimer to this day. In a recent interview with Jon Heyman on MLB Network's podcast 'The Show', he opened up about how close the Yankees came to drafting Trout and how painful it was to see him go on to become one of the greatest players in baseball history: "That one was gut-wrenching."

Mike Trout has proved to be one of the best players of his generation

In hindsight, of course, it's always 20/20, and it's easy to look back and say that the New York Yankees made a mistake, but at the time, they were in a weak position to land Mike Trout. As the last decade has shown, Trout could be the player who has the tools to help the Angels win for years to come.

While the Yankees missed out on a once-in-a-generation talent, they still have plenty of reasons to be proud of their history and their legacy in the MLB. Only time will tell, however, if they'll have the chance to draft the next Mike Trout.