Hanley Ramirez
Fans may cringe at the mention of Hanley Ramirez and wonder what one of the most disastrous free agent signings in franchise history is doing on this list. However, this isn’t about Hanley’s disappointing tenure when he returned to the organization in 2015. When Ramirez was signed as a 16-year old from the Dominican Republic, he quickly developed into an elite prospect.
Ramriez was the most highly touted prospect in the Red Sox farm system when he made his big league debut in 2005. He struck out in his only two plate appearances but his value had little to do with what he did on the field.
Boston used Ramirez as the centerpiece of a trade with the Florida Marlins that brought Josh Beckett and Mike Lowell to the Red Sox. Both veterans were instrumental in delivering a World Series championship in 2007.
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Meanwhile, Ramirez emerged as one of the league’s most exciting young stars in Florida. He won the NL Rookie of the Year award in 2006 and followed with three consecutive All-Star appearances from 2008-2010. He produced a 30/30 season in 2008 to capture his first Sliver Slugger. Hanley earned another of those awards the following season while winning a batting title and finishing second on the NL MVP ballot.
Ramirez struggled with hamstring injuries that sapped him of the elite base-running speed that was a staple of his early years, leading to a couple of sup-par seasons. He rejuvenated his career following a trade to the Los Angeles Dodgers and capitalized with a lucrative free agent deal with the Red Sox that they would quickly regret.
Some of the younger players on this list have the ability to surpass Ramirez some day but based on his peak, Hanley arguably had the most productive career of anyone signed by the Red Sox on the international market. He just didn’t deliver that production in Boston.