When Tim Flanagan was a kid, his father would take him to Kelly Park at night to watch softball games. He remembers the excitement of the crowd and the major-league atmosphere on those hot summer nights. Little did he know that some day he would be roaming the outfield at Kelly and other parks. During his twenty-year softball career, Tim Flanagan played with some of the greatest teams of major softball during the ’80s and ’90s but also played with at least seventeen local teams around Chicago’s Southwest side. His entrance into major softball began when he was playing for the Beavers in the early-’80s at Kelly Park and Mike Tallo asked him to play for Otto’s. He filled in for them in tournaments, and was part of the team that won the Forest Park title in 1981 and also the Chicago Park District championship at Clarendon Park. It was there that he first experienced the intensity of the competition and the talent at the major level of softball. He played with the Viscounts (78-79), Beavers (80-81), Stickmen (’82-’84), Ducks (’85), Touch (’86-’89), Lettuce (’90), Bud 45s (’91-’95), and Swingtown (’96 and ’97). All totaled, he has played in fifteen ASA Nationals. In 1987 Tim and the Normandy Park Crush took second to the Whips in the USSSA Nationals. In 1991 he helped Lettuce finish second to Splinters. He helped Lettuce win Forest Park in 1990 and ’91. In the early ’90s he and Hall of Famers Larry La La Washington, Randy and Mike Lee helped the Safari Tigers win the popular 4th of July He-Man tournament. In 1989 he was named MVP of the NSA World Championship while playing for Touch. In 1982 he was the Davis Square Tournament MVP with the Shamrocks. He was an ASA First Team All-American with Lettuce and a Second Team All-American with Touch and Bud 45s. Besides playing softball, Tim worked with Tim Maher (HOF) on the Chicago Softball Magazine in 1987 and was on the initial advisory board and planning committee for the Hall of Fame. Tim played football for St Rita in the Prep Bowl in 1972 at Soldier Field beating Morgan Park Academy. In 1973 he represented St. Rita in the Catholic League All-Star game played at Comiskey Park. He was a four-year starter in baseball at St. Xavier University and played in nine National Invitational Touch Football championships in St. Louis, MO from 1978 to 1987 with the Chicago Beavers and the Chicago Saints. Despite all the great moments of playing major softball, Tim most fondly remembers playing the outfield with his youngest brother, John, when they played for Bud 45s and Swingtown. In 1999, Tim received the Cook County Superior Public Service Award in the category of Outstanding Public Safety employee. He received the award for his work with street gangs on behalf of the Cook County Adult Probation Department where he has been employed for the past twenty-nine years. He would like to thank his beautiful wife of thirty-two years, Debby, and their three sons, Dan, Brian and Sean for their patience, love and support throughout his playing years.
