He was signed by the Seattle Mariners as an amateur free agent July 30, 1979 and made his Major League debut with the team August 10, 1984. Midway through the 1986 season the Mariners traded him to the Chicago White Sox, where he became an every day rightfielder in 1987.
Known for his power and speed, he put together a series of productive seasons in Chicago. The team traded him, however, after the 1990 season to the Montreal Expos in a deal that brought Tim Raines to the White Sox.
The Expos raised his yearly salary to over US$2 million a season, and his efforts were rewarded with a place on the National League All-Star team. Injuries the following season, however, slowed him down, and after stints with the Boston Red Sox and again with the White Sox, Calderon was finished in baseball, at the age of 31.
His nickname was Ivan the Terrible.
He was a native of Fajardo, Puerto Rico.