Bailey Square is a name given recently to a block-long park dividing South Second Street between Chestnut and Walnut streets in Hamilton's Second Ward.
It originated in the 19th century when John Woods donated the grassy strip for a market place. "The markets included hay and wood," explained Mrs. Heiser in Hamilton in the Making. "Farmers were required to bring their wood cut and piled so that the official wood measurer could mark it off by cords. Then the wood wagons stood in the market place, and citizens came in their own wagons to buy their wood." The square was named in honor of Jim "Boxcar" Bailey, an outstanding athlete at Hamilton High School and Miami University. He was best known as a halfback and linebacker for the Big Blue, but he also played on Hamilton's 1949 state championship basketball team and was a sprinter on the track squad. He earned the nickname "Boxcar" because of his ability to run over potential tacklers. Bailey, who is a member of the Butler County Sports Hall of Fame, continued his spectacular football career at Miami University, playing there under coaches Woody Hayes and Ara Parseghian. One of his memorable college games was when he led Miami to a victory over the University of Cincinnati in the "blizzard bowl" in 1950 He died July 23, 1991, at age 61, in Chicago. In April 1993, the sector surrounding Bailey Square was one of four areas suggested for commercial revitalization in the HyettPalma study of Hamilton. The report said Bailey Square could become "Hamilton's traditional African-American business and entertainment district."