Three trades in particular come to mind. While these trades are nowhere close to the upper echelon of bad trades (think Frank Robinson for Milt Pappas) and the Sox did get good value in return in all three of them, the truth of the matter is that they gave up some pretty good players. Two of them are future hall of famers and the third is now one of the best shortstops in baseball.
First and foremost, we have a trade that went down in 1990. Less than a year after drafting him, the Sox sent Jeff Bagwell to the Astros for Larry Andersen. This is easily the worst of the three trades, as the Sox got a 37-year-old relief pitcher in Anderson for a guy who will likely be in the Hall of Fame some day. You probably know the story with Bagwell. He is most famous for his ridiculous batting stance (where he crouched so low that he might as well have sat on a chair in the batter's box), but he had a pretty good career as well. After leaving the Sox, Bagwell spent his entire career with the 'Stros, compiling 449 career homers with a .297 career batting average. He also won an MVP, a Gold Glove, and went to four All-Star Games.
Next up is a 1988 trade that sent 1986 draftee Curt Schilling along with Brady Anderson to the Orioles for Mike Boddicker. Boddicker did have a good, albeit short, career with the Red Sox (winning 39 games in two and a half seasons), but they gave up Schilling, who became one of the best pitchers of all time, with 216 career wins and over 3,000 strikeouts. Luckily for the Red Sox, they got Schilling back — only it was 16 years later. Schilling won two World Series titles with Boston in 2004 and 2007 and pitched well in his short time, but it was at the back end of his career. I'm sure the Sox would have liked to see how many World Series they could have won with Schilling in his prime.
Last but not least is a much more recent trade that one could say worked out for both teams. The Red Sox sent Hanley Ramirez, Anibal Sanchez and two other prospects to the Marlins for Josh Beckett, Mike Lowell, and Guillermo Mota. While the Sox got two guys in Beckett and Lowell who helped them win a 2007 championship, they gave up Ramirez and Sanchez, who have turned into stars in Florida. Giving up Ramirez is particularly a tough pill to swallow. While he has been questioned for his work ethic and hustle and will likely not be a shortstop for long, Ramirez is one of the best hitters in baseball and is only 27.
Who would you have liked to see play for the Sox in their prime? Pick your choice in the poll below and explain why in the comments section.
Which former Red Sox minor leaguer would you most like to have seen wear a Sox uniform in their prime?online survey
