Umpires & Managers

Terry “Riles” Reily

A graduate of Mt. Carmel High School where he ran track and was on the swimming and diving team, Terry Reilly’s umpiring career started in typical fashion – officiating little league and pony league games. However, his career didn’t end there. As he became more skilled and known as an umpire, he moved into the …

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Willis Miles

In 1951, Willis Miles started a 33-year career that would take him from playing for and managing the Demons to being probably the only umpire to officiate at the world championships of all four major softball organizations. He officiated with the USSSA from 1980 to1994, with the ASA from 1994 to 1998, with the NSA …

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Lee “Donnie” Gardner

A 1964 graduate of Du Sable High School in Chicago where he played baseball and football, Donnie Gardner began playing softball in his church league when he was only twelve years old. During his career, he would go on to play and manage for 32 years in over 2100 games; he would win 56 championships …

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Thomas Kelleher

Having brothers who play softball means that you too will probably follow in their footsteps. For Tom Kelleher that came true in 1963 when he was fourteen and started playing left field with his older brother Bob and the Strikers at Foster Park and other parks on the southside. The Strikers later joined with Mike …

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Ron Dunlap

While Ron Dunlap never played softball, he did go on to become one of the top umpires of the late 70s through the early 90s. That doesn’t mean that Dunlap doesn’t have a background in sports. In fact, he is a former second round draft pick of the Chicago Bulls who also played for the …

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Sal Vasta

Growing up on Chicago’s Northwest Side as a Sox fan, Sal Vasta experienced first-hand the taunts of cross-town rivalry.  But his introduction to 16″ softball through the CYO program quickly made him realize the unity of playing Chicago’s great game. He began the Blues softball team in 1969, playing in various parks around Chicago. Year …

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John Mitchell

Like many great umpires who came before him, John Mitchell switched to the other side of the plate after sustaining an injury that ended his playing career. He played with the Stompers fom 1970 to 1976 as a first baseman and catcher, winning championships at Kosciusko and Amundsen Parks.     Once he injured his knee, Les …

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Paul Leonard

      Blue Island resident Paul Leonard made his transition from a 16″ softball player to an umpire early in his career for a simple reason – he needed money after getting married. In 31 years behind the plate, Leonard would approach each game as if it was the most important of his umpiring career. In …

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James Gemskie

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 …

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Pete Schmit

Pete Schmit holds an interesting first in the annals of high school football; he’s the first football player from St. George High School to be selected to an All-State football team. During the 1939-40 season, he and two other players from Mt. Carmel High School were the only players from the Chicago area to be …

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