Calvin Jackson’s 16-inch softball career started at the age of twelve (1961). He was under the tutelage of Mr. Walton in the Madden Park-Darryl Home Park District softball league, located at 3813 South Rhodes. This league had two divisions: the Intermediate (12 to 15 years) and the Senior League (15 to 17 years).
Calvin first played for the Cavaliers. They won the Madden Park-Darryl Home Park championship for three years in a row. His team soon became eligible for the Senior league where they won this championship for the next two years. At the age of seventeen, he was introduced to the Tavern League at Farmers Field located at 49th Dorchester where he played for the Jive Ten.
In 1969, Calvin was drafted into the Army where he continued to play sports. While in the army, he played 12- inch softball and basketball. In 1970, his team won the basketball championship for the Fort Riley, Kansas Army Base where he was stationed. As a member of a tank battalion, he received a medal for sharp shooting and expert shooting. He was honorably discharged in 1971.
He resumed playing softball with the Iron Man in 1971, and continued to play with them (off and on) until 1989. Calvin also played for the Trillionares (1973), the 203 Stars, and the Flamingos (1974), leading them to the playoffs each year. He helped the Senators (1975) win the softball championship and compete in the Nationals in Marshalltown, Iowa. During that year (1975) the Senators won three championships in the Chicago softball league.
Calvin was known for his fielding, his on – base percentage and his outstanding speed. He could play all positions with equal ability. From 1977 to 1980, he played for the Dating Game, Raven and Sandies in the Cocktail League. He also played for the Cook County Highway Department in the Grant Park Industrial League.
From 1982 to 2002, he played with the Bandits, helping them to numerous championships. With the Bandits, he participated in the Nationals at Marshalltown, Waterloo, and Grand Rapids, Iowa and in Racine, Wisconsin.
Throughout Calvin’s softball career, he played in many parks throughout Chicago and the surrounding suburbs, including Tuley, Coles, Princeton, Grand Crossing, Mount Prospect, Blue Island, Washington, and Argo Park. He also had the distinction in playing in the Chicago Tribune North-South Side All-star game. Calvin feels honored to have to have played with Floyd Glover (HOF), Phil Williams (HOF), Leonard McKinnon (HOF), Dan Dumas (HOF), George (Junior) Franklin, Gene Mathis, Donny Gardner (HOF), Willie (Billy Bumstead) Johnson (HOF), Hank Kemp (HOF), and Austin Ware (HOF).
Besides softball, Calvin enjoyed playing racquetball (where he competed at “A” level) and hunting.
Calvin retired from the Chicago Fire Department after thirty years (1977 to 2007) and still resides in Chicago, Illinois