In March 1893, President Grover Cleveland appointed federal judge Walter Q. Gresham as his Secretary of State, and Gresham hired Landis as his personal secretary. Gresham had a long career as a political appointee in the latter part of the 19th century; though he lost his only two bids for elective office, he served in three Cabinet positions and was twice a dark horse candidate for the Republican presidential nomination. Although Gresham was a Republican, he had supported Cleveland (a Democrat) in the 1892 election because of his intense dislike for the Republican nominee, President Benjamin Harrison. Kenesaw Landis had appeared before Judge Gresham in court. According to Landis biographer J.G. Taylor Spink, Gresham thought Landis "had something on the ball" and believed that Landis's shorthand skills would be of use.