22. Grover Cleveland and Maria Crofts Halpin
During the ’84 elections, Grover Cleveland had a lot to hide. At the time he was having an affair with Maria Crofts Halpin, which resulted in the birth of a son. Halpin was an escort and was typically seen at Grover’s low office. Of course due to her profession, Halpin wasn’t sure he was the father. James Blane, who was Cleveland’s opponent at the time revealed the full story.