Nomar Garciaparra (1994, 1st round)
Nomar Garciaparra emerged during a Golden Age for shortstops, joining Derek Jeter and Alex Rodriguez to form a holy trinity at the position. There was a time when Red Sox fans would vehemently argue that Nomaaah was the best of the trio and the notion wasn’t entirely crazy.
Garciaparra was named Rookie of the Year in 1997 when he hit .304 with 30 home runs and 22 steals while leading the league with 209 hits and 11 triples. He took another leap in his Sophmore campaign, setting career-highs with 35 home runs and 122 RBI to finish as the runner-up for the MVP.
Nomar won a pair of batting titles in 1999 and 2000, sporting a .372 average in the latter season. There were many at the time who compared the sweet swing of Garciaparra to the great Ted Williams and thought he had the best chance of any modern player to hit .400 for a season. He never made it to that level but only six major league players have topped Garciaparra’s career-high .372 average in the years since Teddy Ballgame hit .406 in 1941 (including Williams himself, who hit .388 in 1957).
Garciaparra made five All-Star appearances in his first six full seasons, excluding 2001 when a wrist injury limited him to 21 games. He would return from that lost year to produce two more All-Star worthy seasons but Garciaparra was never quite the same after hurting his wrist and never returned to the astonishing level he showed early in his career.
Unfortunately, injuries continued to pile up for Nomar, spoiling the second half of his career. His relationship with the Red Sox soured during an injury-plagued 2004 season, turning him into a bit of a malcontent and stamping his ticket out of town. He was traded to the Chicago Cubs in a three-team deal that brought Orlando Cabrera in as his replacement at shortstop, depriving Garciaparra of being part of the curse-breaking World Series championship run that year.
His tenure in Boston may not have ended well but it started out as promising as any position player in recent memory. Fading under the weight of multiple injuries in the second act of his career kept him out of Cooperstown but there’s no doubt that Nomar was well on his way toward being an all-time great hitter during his years in Boston. Garciaparra was recognized for those efforts in 2014 when he was inducted into the Red Sox Hall of Fame.