Born at Edina in Grand Bassa County, he was elected three times on the True Whig ticket.

Conditions worsened, as the cost of imports was far greater than the income generated by exports of coffee, rice, palm oil, sugarcane, and timber.

Whenever the British and French seemed intent on enlarging at Liberia's expense the neighboring territories they already controlled, periodic appearances by U.S. warships helped discourage encroachment, even though successive American administrations rejected appeals from Monrovia for more forceful support.

Ethnic struggles with the Kru, Gola, and Grebo tribe who resented incursions into their territory occurred several times during Cheeseman's reign.

Cheeseman and his wife are buried in Edina in elaborate graves adjacent to their mansion, which is now in ruins and overgrown with vegetation.