After retiring as a player and leaving the Colts, Anson briefly managed the New York Giants. He ran several enterprises in Chicago, including opening a billiards and bowling hall and running a semi-professional baseball team he dubbed "Anson's Colts". Anson also toured extensively on the vaudeville circuit, performing monologues and songs. Many of his business ventures failed. As a result, Anson lost his ownership stake in the Colts (by then known as the Cubs) and filed for bankruptcy. Anson was inducted into the National Baseball Hall of Fame in 1939.