The Red Sox selected Jacoby Ellsbury with the No. 23 overall pick in 2005. He made his big league debut two years later and emerged as a key contributor to the 2007 World Series champions. Ellsbury was 7-for-16 (.438) in the four-game sweep of the Colorado Rockies.
The following season, Ellsbury finished third in the Rookie of the Year race in a season highlighted by a league-leading 50 steals. He led the league in stolen bases three times with the Red Sox, including a franchise record 70 steals in 2009.
Ellsbury had one monster season in 2011 when he finished as the runner-up for the AL MVP award. He hit .321/.376/.552 with 32 home runs, 105 RBI, and 39 steals. He won the only Gold Glove and Silver Slugger awards of his career that season and made his lone All-Star appearance.
While he would never again approach those type of power numbers, Ellsbury had a couple more solid seasons with the Red Sox. He helped the team win another World Series in 2013 before signing a lucrative long-term deal with the New York Yankees when he hit free agency.
Fans turned on their former center fielder for spurning them for their biggest rival. However, that resentment has mostly faded given that his contract with the Yankees has turned out to be a bust while the Red Sox field one of the best outfields in baseball.
Ellsbury did plenty during his seven years in Boston to be considered a successful first-round pick.