Jack “Swifty” Flynn

In his 2001 biography of Mike Royko, Richard Ciccone quotes Tim Weigel saying that he was disappointed that Royko became a pitcher because according to Weigel “there’s no such thing as a good pitcher.” Although Weigel was a Yale graduate, starting halfback on their football team, and a legendary local sportscaster, apparently he hadn’t been around sixteen-inch softball to realize that there were a lot of great pitchers.


And one of those pitchers was Jack Flynn. He pitched for the Rockets, a Canaryville team from 47th Street. Flynn was seventeen in 1950 when he led the Rockets to the championship in the Alderman Clarence Wagner Softball Tournament at Davis Square Park. He later played for the Madonna Council Knights of Columbus and helped them with the 1955 championship with out fielder Jim McCardle (HOF) and Flynn’s coach/pitcher/mentor Tom “Turk” Corcoran.


Jack Flynn also pitched for the Burlington Railroad in the Grant Park railroad League and on the South side for the Dutch Reformed Church team called the Shoes in the late ‘60s. He pitched money games almost every Sunday for the Two – 45s with Hall of Famers George Wagner and Jack Lyman. Over the years, he pitched several one run games, a feat almost unheard of in the high scoring world of sixteen-inch softball. In 1957 in has best game, Flynn and his talented teammates came within one out of a rare shutout when Madonna K of C defeated St. Albert the Great at Armour Square Park 17 – 1. He received his nickname at this game. St Albert’s lone run came with two out in the last inning when an infielder’ error allowed the runner to score. Both teams signed the ball for Flynn as a souvenir. A few weeks later, St Alberts won the K of C championship. In a show of respect, they invited Jack and his wife, Dorisann, to their victory party.


In 1969, the Flynns moved from Bridgeport to Waukegan where they raised their seven children. They now have twelve grandchildren and a great granddaughter.