 With the financial aid of a white friend, Robert A. Jenkins, Cheatham attended Shaw University, a historically black college in Raleigh, North Carolina, where he graduated in 1883.He worked briefly as a school principal before being elected as the Register of Deeds for Vance County (1884–1888), which was majority black and Republican.In this period, the Democrats had regained control of the state legislature, but many blacks continued to be elected to local office, as the state was more than 30% black.