When Upham arrived in the town of DeVall's Bluff, in April 1865, most of Arkansas was under Union Army occupation. Under the army's policies if you wanted to do business in areas under occupation, you needed the right permits issued by the local commanders. General Shaler was the commander of a sizable district in Eastern Arkansas and Upham was in a position to exploit the conditions for his benefit. General Shaler placed Upham in charge of issuing permits with the result that if you wanted a permit, you had to make Upham happy.
Most people would have made use of this opportunity to simply collected some bribes. However, Upham was interested in gaming the system to the hilt. He demanded shares in the ownership of the enterprises that local businessmen could only create with the help of the licenses that were under his control. Upham aimed for as much as a 50% ownership share and often got it. Upham received shares in such profitable endeavors as cotton plantations, a dry goods store, saloons and steamboats. GIven the fact that the price of cotton was at its all time high due to the Civil War's disruption of the cotton supply and the fact that the permits often enabled those who gained them to have monopolies, Upham had little difficulty persuading local businessmen to accede to his demands. By July 1865, Upham was in a position where he could travel to New York City, retire all of his debts and bring both his wife and his brother Henry N. Upham to Arkansas in a state of prosperity.
During the ensuing years, Upham moved to Woodruff County where he built up a fortune. He was one of the leading landowners in the county. His position was such that when regular government was restored and elections were held, Upham was able to get himself elected to public office as a state representative. As can be expected, Upham entered office with his customary hard work and dedication and and soon he became one of the leading members of the state house of representatives. Life was good.
Perhaps the most striking aspect of the election that Upham attained public office was that for the first time newly freed blacks were able to vote and gain elective office. However, not everyone was pleased with the results."The First Black Legislators"