The need for affordable working class hotel space south of downtown came about as the result of the completion of Union Station in 1914. Raymond H. Sanneman designed the Monroe Hotel in 1920 for the Dubinsky Brothers, and Elelman-Fleming Construction Company served as the general contractor. The five-story hotel was constructed of reinforced concrete with brick and terra cotta at an estimated cost of $150,000.
Political boss Thomas J. Pendergast purchased the Monroe Hotel in 1924, and he hired Sanneman to design a two-story building adjacent to the south side of the hotel that would serve as the headquarters for his Jackson County Democratic Club. Pendergast operated out of the two-story building at 1908 Main until the late 1930s. Pendergast had a doorway installed between his second floor office and the hotel, giving him a clandestine entry point. After Pendergast's release from prison for income tax evasion, a Federal Court ordered the doorway to be sealed and barred Pendergast from any further political activity. The hotel closed its doors in 1971.
After sitting vacant for more than 30 years, renovation to the Monroe Hotel was completed in summer 2006, and the hotel is now home to 8 luxury condominiums. The condos range in size from 1,930 to 2,500 square feet (230 m 2).