For a franchise so commonly associated with free agency, the New York Yankees have have had quite the history in Major League Baseball's annual draft. Play it safe and cap your potential; take a risk and you could bust.
Not every prospect pans out like Derek Jeter. And the Yankees have learned that the hard way.
The team has never exactly been knowing for homegrown talent. It's not to say they are incapable of producing their own—just look at Robinson Cano—but the Yankees have had the tendency to build through free agency over recent decades.
And the names on this list are partially a reason why.
Because you never really know what you're getting with an 18-year-old high school kid. Maturity is arguably the most important factor when evaluating a teenager who is set to receive a signing bonus exceeding $1 million; however, you would be surprised how many draft selections fail to possess it.
For the younger fans, names like Phil Hughes and Joba Chamberlain might come to mind considering their seemingly endless potential upon entering the big leagues. But in the end, both players have World Series rings and remain wearing Yankee uniforms to this day.
You see, this list is reserved for those who likely never wore the pinstripes.
This list is for those who failed to even flirt with their potential.
Let's take a look at someone of the biggest New York Yankee draft busts in recent memory.
Brien Taylor (1991)
In a matter of decades, Brien Taylor went from being the most sought-after talent in the game of baseball to an inmate at Federal Prison in New Jersey.
The first overall selection in the 1991 MLB draft, Taylor was commonly perceived as one of the greatest pitching prospects to enter the league. Unfortunately, his 99 mph fastball from high school never translated to the professional level, and a shoulder injury suffered during a fist fight helped cut his career short.
Following surgery, Taylor's velocity dropped to the low 90s, and command issues prevented him from advancing further than the Double-A level. To this day, he stands as one of only three first overall draft selections (through the year 2010) to never make an appearance in the major leagues. Taylor is serving a 38 month jail sentence for cocaine trafficking charges.
David Parrish (2000)
Son of former Detroit Tigers catcher Lance Parrish, David was a catching prospect out of Michigan who was expected to provide depth on an aging Yankees roster at the turn of the millennium.
However, his highly touted power never reached its potential, and Parrish failed to make it past Double-A ball. As the 28th overall pick in the 2000 MLB draft, he received an outrageous $1.42 million signing bonus from the Yankees but totaled just 38 home runs in nine minor league season before hanging the cleats up for good in 2008.
Jon Skaggs (2001)
After going a combined 22-6 over four years at Rice University, Jon Skaggs was taken with the 42nd overall pick during the 2001 MLB draft. The Yankees saw a large frame (6'5", 225 lbs) and a power arm that they hoped would help solidify their rotation.
But that wasn't the case. Instead, New York received an oft-injured minor league pitcher who struggled with consistency. Skaggs experienced a sliver of success with the 2004 Tampa Yankees before posting a 3-10 record with an ERA over six with Tampa and Trenton in 2005.
Following his poor performance in 2005, Skaggs was cut by the Yankees. He spent one more full year with the Houston Astros minor league organization before being cut by the Tampa Bay Rays as camp ended in 2007.
Eric Duncan (2003)
Another elite high school prospect, Eric Duncan was a New Jersey native slated to be the next Derek Jeter in the Yankees' lackluster farm system. He was a prized third baseman taken with the 27th overall pick in the 2003 MLB draft and was rated as high as the 36th-best prospect by Baseball America before the 2005 season.
But, just like the rest of baseball's "busts," Duncan didn't pan out. A massive long-term contract for Alex Rodriguez pressured the Yankees into switching Duncan over to first base. However, with the transition came a decrease in production.
Early minor league success was followed by a continuous drop in batting average. Whether his decline was a product of the Yankees rushing him through the organization or simply a lack of true major league talent, we will never know. Duncan was cut by New York in 2009 and announced his retirement from baseball after suffering a torn quadricep in 2012.