In 1915 Conn's growing debt crisis forced him to seek a buyer for his assets. All of Colonel Conn's holdings were bought by a group of investors led by Carl Dimond Greenleaf (b. Wauseon, Ohio 27 July 1876; d. Elkhart, Indiana 10 July 1959). Conn met Greenleaf during his years in Washington, D.C., and invested in some grain mills in Ohio which Greenleaf owned. Initially Conn held onto ownership of The Elkhart Truth, but a few months after the sale of his other holdings, Conn sold The Elkhart Truth to Greenleaf and to a local entrepreneur Andrew Hubble Beardsley. The sale was detrimental to Colonel Conn's marriage. They divorced, and Mrs. Conn was allowed to retain a house in Elkhart in which she lived until her death in 1924. Colonel Conn meanwhile was allowed to keep his home in Los Angeles, California. He spent virtually the remainder of his life there and only returned to Elkhart once in 1926 to visit his sister. He remarried to a very young woman while in California, and they had a son twelve years before Conn's death in 1931. Once a very wealthy and influential man, he died almost penniless. His estate didn't have enough money in it to afford a grave marker, and a hat was passed around the horn factory to collect enough money to buy one.