On July 25, 1960, Governor Cecil Underwood addressed the Republican National Convention in Chicago. The 37-year-old Underwood backed Republican presidential candidate Richard Nixon and disparaged Nixon’s Democratic opponent, John F. Kennedy.
Less than three months after the 1960 Democratic primary in West Virginia, Underwood implied that Kennedy had beaten his opponent, Hubert Humphrey, by essentially buying votes. The money Kennedy spent in West Virginia has always been a controversial part of the story. For his part, Humphrey also felt that the wealthy Kennedy family had bought the Mountain State for JFK.
A few months later, Nixon lost the 1960 general election to Kennedy in a close contest where money once again played a major role.
Underwood was also campaigning for himself in 1960. Prohibited by the state constitution for running for a second term as governor, Underwood lost to incumbent Democratic Senator Jennings Randolph in the November general election race for the U.S. Senate. It was Underwood’s first ever political loss. He wouldn’t be elected again to public office for 36 years, winning the governorship for a second time in 1996—on his 74th birthday.