James Gemskie began his softball career in 1949, playing around Chicago’s Northside. From 1949 through 1953, Gemskie also played football for DePaul Academy, winning All State Honorable Mention. He then went on to play football for three years at St. Ambrose, earning a degree in Political Science. After a knee injury later ended his softball career, Gemskie switched to the other side of the plate when he joined the Umpires Protective Association in 1960, and began umpiring high school baseball and Chicago Park District softball games. In 1970 he was appointed UPA’s Chief Umpire, and held that position until 1998. During his tenure as Chief Umpire, Gemskie was responsible for the umpires at leagues around Chicago and the suburbs, including the Classic League in Evanston. Overall, Gemskie dispatched 115 umpires (including his three daughters) to more than fifty leagues in and around Chicago. Gemskie was fortunate to be behind the plate for some classic matches between some of the greatest teams during softball’s golden era. However, Gemskie claims that one of his toughest assignments was umpiring the Hearing Impaired League during the early 1980’s, because of their reliance on the signed word rather than the spoken word. When not umpiring, James worked for the Chicago Board of Education as a teacher, counselor, and coach for 35 years. He currently coaches wrestling, 16″ softball, and baseball at Amundsen High School in Chicago. Two of Gemskie’s fondest memories in softball involve his daughters. One is umpiring with daughters Michele, Maria, and Valerie in the North Shore Women’s Softball League in Evanston The other is coaching Amundsen High School’s softball team against a formidable opponent, Walter Payton College Prep, and their formidable coach – his daughter Valerie. In addition to their daughters, James Gemskie and his wife, Josephine, have three grandchildren, and reside on Chicago’s Northwest side.