Colonel Conn was a colorful personality of the show biz sort. He believed that he could do anything. His career grew far beyond the confines of horn making. In 1880 Conn was elected Mayor of Elkhart on the Democratic ticket. He was re-elected in 1882 but did not finish the term. Ten days before the general election in 1888, Conn was drafted as an emergency candidate for the Indiana House of Representatives by the Democrats, and won the election. In 1892 he was elected to the United States Congress as Representative of the 13th District of Indiana. Two years later he was re-nominated, but declined the nomination unless the party permitted him to make the canvass on a "reformed" platform. The party would not permit this, and accepted his declination. In 1908 he ran for Governor of Indiana and lost; in 1910 he ran for Senator. Conn's term in the House was one that provided help for Civil War veterans seeking assistance.