Yankees Draft Preview 2016: Remembering the 5 biggest busts in franchise history

Not every draft pick is going to turn into Derek Jeter or Don Mattingly. Most of them won't even turn into Phil Coke. Baseball is a brutal game, even for the most talented amateur prospects. Pre-draft accomplishments and makeup can increase stock, but it also creates the possibility of unfulfilled hype.

The Yankees have had draftees who never amounted to much in the majors, but they were still able to reap some value out of them through trades. Charlie Spikes turned into Graig Nettles. Matt Drews turned into Cecil Fielder. C.J. Henry turned into Bobby Abreu. Unlike those three players though, these five former prospects let the Yankees down while they were in the organization. Their potential just never shined through.

5. Dennis Sherrill

Drafted: 1974, 1st round, 12th overall
Position: Shortstop
School: South HS (Miami, FL)

Long before Cito Culver was struggling to hit his weight after being a surprisingly pick in the 2010 MLB Draft, there was Dennis Sherrill. A strapping, good-looking shortstop out of high school, the Yankees elected to draft Sherrill ahead of another talented 18-year-old at the same position. One pick after the Yankees nabbed Sherrill, the Cardinals drafted Garry Templeton. The latter played in 2,079 games over 16 years, racked up 27.6 WAR, made three All-Star teams during his time with the Cardinals and Padres, and led the National League in triples three years in a row. That is an excellent career.

Meanwhile, Sherrill appeared in all of five games in the majors and had an OPS over .575 just twice in his seven minor league seasons. His one good year in '78 helped him to a cup of coffee and he returned again briefly two years later. Sherrill was gone from baseball by 1981, Bucky Dent's last full season with the Yankees. Had Sherrill fared better, that could have been his time to shine. Instead, the Yankees struggled for over a decade to fill the void at shortstop until Jeter came along.

4. Andrew Brackman

Nick Laham/Getty Images

Drafted: 2007, 1st round, 30th overall
Position: Starting pitcher (RHP)
School: NC State

A 6'10" monster who unsurprisingly played some basketball as well at NC State, Andrew Brackman's fastball pushed 97 mph, and he also showed off a dazzling breaking ball on the mound. He seemed to have clean mechanics too, even though he went through a "dead arm" faze toward the end of his time with the Wolfpack. He seemed like a risky signing since there was concern that he might need surgery, but the Yankees went for it anyway, inking Brackman to a big four-year, $4.55 million deal.

Sure enough, just about a week after agreeing with the Yankees, Brackman underwent Tommy John surgery. That is not necessarily a death knell for a draft pick--after all, MLB's top pitching prospect Lucas Giolito needed Tommy John right after the Nationals selected him. However, Brackman never recaptured that pre-surgery form. He never had any control, exhibited most painfully during his Triple-A stint in 2011, when he had an eye-popping 7.0 BB/9 to accompany a 6.00 ERA in 96 innings. He made his MLB debut that year as a September call-up and appeared in three games, but the Yankees cut bait during the off-season. Brackman never made it back to The Show and was done pitching at age 27.

3. Eric Duncan

Nick Laham/Getty Images

Drafted: 2003, 1st round, 27th overall
Position: Third base
School: Seton Hall Prep (West Orange, NJ)

A nigh-legendary slugger from nearby northern New Jersey, Eric Duncan quickly became a popular prospect in the Yankees' system and seemed like a good bet to take his place in the future of the Yankees' infield. It didn't matter that they traded for Alex Rodriguez during that time and blocked him at third--if he hit enough, they would find a spot for him. Duncan indeed hit .258/.357/.473 in A-ball in 2004 and despite a slight decline in '05 with Trenton, he crushed the Arizona Fall League, earning MVP honors.

Sadly, Duncan could never solve high minors pitching. In four seasons of Triple-A ball, he only hit .226/.290/.343. Even worse, his numbers declined every year he returned to Scranton. He was once ranked by Baseball America as the 36th best prospect in the game. Yet he never made it to the major leagues--at least as a player. Duncan retired in July 2012, spent a couple years as a volunteer coach for Seton Hall Prep again while pursuing his degree, and was hired by the short season-A Staten Island Yankees in 2015 to be their hitting coach. Duncan will return to that job in 2016; perhaps one day, he can make it to The Show on the sidelines.

2. Drew Henson

Photo credit: Rick Stewart/Getty Images

Drafted: 1998, 3rd round, 97th overall
Position: Third base
School: Brighton HS (Brighton, MI)

Don't let Drew Henson's draft position fool you. He was every bit the prospect that Duncan was and more, winning High School Player of the Year honors from USA Today and Gatorade, matching Derek Jeter's draft resume from six years prior. No one thought that he would sign since he was also an amazing blue chip quarterback with a commitment to the Wolverines. Henson was so good at football that he later legitimately competed with Tom Brady for playing time in Ann Arbor. Henson stunned the sports world by signing a six-year, $17 million deal with the Yankees when he was drafted in '98 and played ball during the summers between college, where scouts were awestruck by his power potential.

The Yankees were so fond of Henson that when they had to include him in a midseason 2000 trade with the Reds for Denny Neagle to bolster the rotation, they reacquired him in a trade for Wily Mo Pena in spring training 2001. Baseball America called Henson the ninth best prospect in baseball entering the 2002 campaign. He struck out far too much though, looked increasingly awkward at third base, and could not top a .750 OPS in Triple-A during a high-offense era. Henson appeared in eight MLB games between '02 and '03, but that was the end of his baseball days . He tried going back to football and flopped with the Dallas Cowboys, too. So Henson finished his sports career as a bust in two sports, the anti-Bo Jackson. Ouch.

On the bright side, Henson later impressed the Yankees enough with his acumen that he became a Rookie Ball hitting coach for a couple years and now serves as a scout. Here's hoping his front office career fares much better.

1. Brien Taylor

Jim Gund/Getty Images

Drafted: 1991, 1st round, 1st overall
Position: Starting pitcher (LHP)
School: East Carderet HS (Beaufort, NC)

Sigh.

Only twice have the Yankees held the top overall pick of the draft. The first time, in 1967, they chose Ron Blomberg, a first base/future pioneer DH who made it to the majors and had some success before injuries slowed him down. He wasn't what the Yankees had hoped, but "Boomer" was still a popular player who had an excellent .302/.370/.486 triple slash and a 148 OPS+ in parts of 400 games from 1969-76. Brien Taylor was the other top overall pick, and his background is something else altogether. That link above is a must-read from FanGraphs about Taylor's story (as is this ESPN oral history).

Agent Scott Boras called the tall lefty the best high school prospect he'd ever seen. In the first possible major prospect list he could appear on after being drafted, Baseball America ranked him #1 overall prior to '92. After a 2.57 ERA, 10.4 K/9 campaign in 27 starts with High-A Fort Lauderdale, he was ranked the #2 overall prospect before the '93 season, trailing only Chipper Jones. He had a fine season at age 21 in Double-A Albany. Then... it was suddenly all over after a fight in the 1992-93 off-season:

A few weeks after the end of the season and a few days before his 22nd birthday, an argument between Taylor’s older brother Brenden and his girlfriend’s family turned into a fight, and the best pitching prospect in baseball threw a punch that didn’t connect. Boras initially called the injury a bruise, but the reality of the situation was much more dire. Brien basically ripped his left arm right out of the socket, dislocating his shoulder and tearing both his labrum and capsule.

"I can remember [Dr. Frank Jobe] sitting me down," recounted Boras back in 2006. "He said, This is one of the worst shoulder injuries I’ve ever seen,’ and I believed it. The way he tore it was unnatural."

Indeed, Taylor was never the same. The high-90s fastball and power curve were essentially gone. He missed the entire '94 season recovering from shoulder surgery, and he never got out of A-ball or lowered his ERA below 6.00 over the next four seasons. To this day, Taylor remains one of only two top overall picks to never make it to the majors. His personal life was even worse, as in November 2012, he was sentenced to 38 months in jail for selling crack. Taylor was released in September 2014, and one can only hope that his outlook improves from that low point.

Say what you want about Drews, Brackman, and other Yankee starting pitcher prospect flameouts. Taylor was the biggest blow. The Yankees of the late '90s were dominant but just imagine how they could have been if Taylor reached his potential.

Portions of this post have been reproduced from another draft history post I wrote in June 2014.