riley began participating in local theater productions with the adelphians to earn extra income. during the winter months, when the demand for painting declined, riley began writing poetry which he mailed to his brother who lived in indianapolis. he acted as riley's agent and offered the poems to the "indianapolis mirror" newspaper free of charge. his first poem was featured on march 30, 1872, under the pseudonym "jay whit". riley wrote more than 20 poems to the newspaper, including one that was featured on the front page.