Getty Images A power-hitting third baseman, Duncan was drafted in the first round (27th overall) in 2003. Only problem is the Bombers also traded for another third baseman — Alex Rodriguez, who moved from shortstop to third to appease Derek Jeter. The Seton Hall Prep star had promising 2004 and '05 seasons, yet never broke through that thick physical and emotional membrane between the minor and majors. Duncan posted a .226 batting average in four seasons of Triple-A ball. Duncan retired in 2012 without making a single ripple with the Yankees.
4. Cito Culver
The shortstop was drafted in the first round of the 2010 draft, presumably to replace another first-round pick — Derek Jeter, who was about 15 years into his Bronx Bombers career. The problem is Culver may have had as good or better a glove than the iconic Yankees shortstop, but shared none of the clutch, Hall-of-Fame hits that Jeter waved in his wand of a baseball bat. Since he was just 17 when he was drafted, Culver is just 27 years old. The Yankees were warned that Culver was a bust and chided them for spending such a high pick on him. To his credit, Culver is still toiling in the minors, clawing toward his dream. But the big-time, big-league ship has long since sailed. Culver's next game in the Bronx will be his first.
3. CJ Henry
Another shortstop who failed to fill Jeter's bejeweled shoes, Henry was picked by the Yanks in the first round (17th overall) of the 2005 draft. Unlike Culver, who was picked when Jeter was in the dusk of his career, Henry was picked in Jeter's prime. The $1.6 million Henry got was like coins buried in the couch for a wealthy club like the Yankees. But still, Henry never made the majors. The Oklahoma native was 19 when he was drafted, left the game when he was 29, and then played college basketball.
Perhaps the more gruesome part of the Henry pick was the players picked after him in '05, such as Jacoby Ellsbury, Colby Rasmus, Jed Lowrie and Clay Buchholz.
Getty Images The southpaw pitcher, who soared to 6-foot-10, with a 99 mph fastball, looked like Randy Johnson. But he pitched like Howard Johnson. Brackman was drafted by the Bombers in the first round (30th overall) in 2007. The North Carolina State alum signed a four-year deal out of school worth $4.55 million, including a $3.35 million signing bonus. Brackman had Tommy John surgery just days after the Yanks picked him, and pitched in a grand total of three games in pinstripes. The one-time promising pitcher was done pitching at age 27, retiring in 2013 to pursue a basketball career.
1. Brien Taylor
No list is complete unless it leads with the talented Mr. Taylor. Those of us who were reared on the '80s Yanks and were sick of seeing the Mets bogart the bold ink were super-psyched to see Taylor in a Yankees uniform in the '90s. He would be our version of Doc Gooden. Not only would Taylor break the Mets' hold over Gotham's heart but he would also break the hex the Mets had over the Yanks.
The 1991 draft was just the second in which the Yankees had the top overall pick — the first was used to bag Ron Bloomberg in 1967 — and Taylor was as close to can't-miss as a pitcher gets. Super agent and eternal antagonist Scott Boras branded Taylor the best prospect he'd ever seen. Not only was Taylor armed with a 99 mph fastball, he was a southpaw, which was, is, and will always be baseball gold.
Taylor was considered the second-best prospect before the 1992 season, and the top-ranked prospect entering 1993 (according to Baseball America). Then, a few days before his 22nd birthday, Taylor got sucked into a brawl that literally tore his left shoulder out of the socket. Ace status over. Career as a frontline starter over. Boras was told by Taylor's surgeon that the injury was one of the worst he'd ever seen.
In Nov. 2012, Taylor was pinched for trafficking cocaine. He did two years of a 38-month sentence. Even worse, the Yankees lost their future franchise player, a no-doubt ace in the mold of Gooden or Clemens or Maddux.
Twitter: @JasonKeidel