Biggest draft busts in Yankees history

When we hear the term "draft bust," we automatically think of the NFL. College football is a more high profile sport than baseball, and we can see them on TV every Saturday. College baseball is not as popular, and unlike the NFL, many ballplayers come from high school and far-flung places in Latin America. In most cases, they are faceless names. Baseball has more than its share of busts, though.  Here are some of the Yankees' biggest busts, in no particular order.

Brien Taylor

OK, OK. I said no order, but Taylor has to be first on any list. The first overall pick in 1991, one can only daydream of the "Core Four" becoming the "Fab Five" (Derek Jeter was his roommate). Alexis Brudnicki, over at MLB News, provided the following quote from scout Ron Rizzi, who has spent 53 years in the game. "The best pitcher I ever scouted was Brien Taylor. He would have been one of the greatest pitchers in the history of baseball." That entire article is worth the read. It hurts even to read that because it never came close to happening. Taylor's professional career did begin with a lot of promise. In 1992, he would pitch to a 2.58 ERA in 27 starts for A+ Fort Lauderdale. It included giving up only three home runs in 161 innings and 187 strikeouts. The Yankees promoted him to AA Albany-Colonie for 1993, and he still represented well. A to AA is considered a big jump in MiLB, and he hurled to a 3.48 ERA in 27 starts and 163 innings. Once again, he kept the ball in the park, giving up only seven home runs. His success all ended during the off-season. Andrew Marchand in a 2014 article, provided this account from Taylor's agent, Scott Boras: "Brien was stellar, dominant, on his way. He was going to the big leagues and was going to be all we thought he was going to be, then there was that unfortunate evening in North Carolina in 1993 that he got a call that his brother was getting beat up at a bar. He was home in bed. He gets out of his bed. He goes over to find his brother and protect him. A guy takes a swing at him, and he puts his left arm up, his hand and arm take the force of the swing. It pushes his arm back behind his head. "I take him to Dr. Frank Jobe. He looks at me. 'This is the worst rotator cuff tear I've ever seen. It is completely off the bone.' So he had to have that surgery."

Taylor would never be the same, his knee-buckling power curve all but gone along with his once 98-100 mph fastball velocity. He missed 1994 from his surgery and never played again above A ball. The best ERA he would post after surgery was 6.08 and the Yankees would release him after the 2000 season.

Unfortunately, the sad tale does not end there.  In 2012, Taylor was sentenced to 38 months in prison for selling crack.

Dennis Sherrill

The 12th overall pick in 1974 never lived up to the promise of his draft position. Instead of being part of the bridge between Bucky Dent and Jeter, the shortstop from Miami would play in only five MLB games total during the 1978 and 1980 seasons. Instead of Sherrill, the likes of Alvaro Espinoza and Bobby Meachum would play the position. Sherrill would slash .234/.293/.322 in seven minor league seasons.

Drew Henson

It's interesting how careers can intersect and have a later impact. Henson's draft bust status led the Yankees to acquire Aaron Boone at the 2003 trade deadline, and we all know what happened in the playoff game seven against the Red Sox later that season. One doesn't usually consider a third-round draft choice a bust, but Drew is an exception. His status as a QB at Michigan who was battling Tom Brady for a starting spot led to uncertainty about his intentions and devotion to baseball, but he was a first-round talent. After the 1998 draft, he would sign a six-year $17 million contract to play baseball exclusively. He played well in the minors, including early 2000 for AA Norwich. He was batting .333 when the Yankees sent him to Cincinnati as part of the Denny Neagle trade. The Yankees still coveted him even after the deal and received him back in 2001 for Wily Mo Pena. From 2001-2003, he would never hit above .240 for Columbus and played a total of eight games at the Major League level and get one hit in eight at-bats. After realizing that he was not going to be Boone's replacement in 2004, he announced he was leaving the Yankees. Henson went back to football and threw a total of 18 passes for the Dallas Cowboys. On March 24, 2020, the Michigan Baseball Hall of Fame announced Henson's coming induction.

Drew Henson 2002 Topps Traded

Andrew Brackman

Brackman was the 2007 first-round draft pick out of NC State. A big guy at 6'10" with a smoking fastball and plus breaking ball, the Yankees gave him a four year, $4.55 million contract. Elbow issues for the 30th overall pick dropped his draft status. After his signing, the team sent him to Dr. James Andrews to look at lingering concerns, who determined he needed Tommy John surgery. Even after surgery, Keith Law had him in the Top 100 prospects, while Baseball America and Baseball Prospectus had him as in the list of top ten Yankee prospects. He would pitch to a 5.38 ERA over five minor league seasons, but had a steady 2010 and was called up to the Yankees in 2011 to pitch in three games, 2 1/3 innings, and give up no runs. The Yankees had an option after 2011 that would have boosted his original contract to $13 million, and the team declined to exercise it. He would go on to pitch 75 innings in the Reds and White Sox organizations until the end of his career in 2013.

Eric Duncan

Duncan was the 27th overall pick in 2003 out of Northern New Jersey. Although blocked by A-Rod at third base, the Yankees saw him as a future piece, even if they would need to find him a new position at first base. Before 2005, Baseball America had him as the Yankees top prospect and 36th best prospect in all of baseball. He did well in the lower minors but hit the wall in AAA. The Yankees would release him after 2009, and he would move on to play in the minor leagues for the Braves, Rockies, Royals, and Cardinals organizations. His minor league career resulted in a .249/.320/.411 slash line. Duncan never played in the major leagues, but would become the hitting coach for the Staten Island Yankees in 2016 and then Tampa during 2017-2018. He then joined the Marlins organization for 2019 and was promoted to batting coach for the 2020 season.

Dave Parrish

With excellent bloodlines as the son of Lance Parrish, the Yankees had high hopes for their 28th choice in the 2000 draft. He would hit for a .241/.321/.349 slash line and 38 home runs over eight minor league seasons, and never make it past AA in the minors. He was also not a great defensive catcher, limiting his value. In May of 2004, while the Angels were turning a double play, Jorge Posada was struck in the face and broke his nose. While missing a few games, Parrish was called up to the majors to backup John Flaherty but saw no action.