Sometimes, offseason acquisitions work out. Sometimes they don't. Sometimes, they are spectacular failures.
Ivan Calderon was part of the big makeover of the Red Sox in 1993. He was brought in to play right field and designated hitter, sharing both positions with fellow new acquisition Andre Dawson. In the late 1980's/early 1990's, Calderon was viewed as a decent five tool player. He hit for power, could steal bases, had decent contact skills and a good batting eye, and he was pretty good in the field. Calderon was an All Star in 1991 while with the Expos, but he was injured for much of the year in 1992.
The Red Sox acquired him anyway, buying low on him and only giving up Terry Powers and Mike Gardiner, neither of whom did much after that. Calderon though, continued to have injury problems and only played in 73 games. He was still a good defensive player putting up a WAR number on defense of 1.0, but his hitting stats were atrocious. Calderon went .221/.291/.291 with only one home run and 19 RBIs. He did steal four bases, but was also caught twice. Calderon was released in August and hooked back up with the White Sox, but it was clear his career was over.
Calderon was murdered in 2003 when he was shot seven times in the back and head in a bar in Puerto Rico.