Born in New Hampshire, Willey was educated in Dartmouth, Massachusetts and studied law in New York. In 1822, he settled in Cleveland and began practicing law. He soon gained recognition as a witty debater, which earned him three years in the Ohio House of Representatives (1827–1830) and three more in the Ohio Senate (1830–1832) as a Jacksonian Democrat. Willey quickly became attached to Cleveland and was subsequently elected mayor for two terms after the city was chartered in 1836. Willey was responsible for writing the municipal charter as well as many of the original laws and ordinances.