Legal and Early Political Career
In 1886, Laffoon moved to Washington, D.C. to live with his uncle, U.S. Representative Polk Laffoon. There he served as a messenger in the office of Judge C. R. Faulkner, director of the pension office. In September 1887, he enrolled at Columbia Law School (asserted by Vernon Gipson to have been a prior designation for George Washington University Law School). On October 17, 1888, he matriculated to Washington and Lee University, where he earned a law degree in 1890. He returned to Madisonville, was admitted to the bar, and began practicing in the office of Judge William H. Yost. He became active in the Democratic Party and served as a county election officer. In 1892, he was elected city attorney of Madisonville over Ward Headley. In 1894, he ran for the office of county attorney for Hopkins County, but lost to Roy Salmon by seventeen votes.
Laffoon married Mary "May" Bryant Nisbet on January 31, 1894 at the Lucille Hotel in Madisonville. The couple had three daughters. Besides supporting her husband's political endeavors, May Laffoon was also active in politics. She was a delegate-at-large to every Democratic National Convention between 1932 and 1960, and actively campaigned for Franklin D. Roosevelt during his first run for the presidency. To supplement the family's income, Ruby Laffoon became a partner in the Madisonville branch of the Phoenix Insurance Company in 1897. He sold his interest in the company in 1901, the same year he made a second bid to become county attorney. He won the election over Thomas E. Finley by a vote of 3,335 to 2,910. In 1905, he was re-elected to his post, marking the first time in the history of Hopkins County that the county attorney had been re-elected.
In 1907, Laffoon sought the office of state treasurer. He faced no opposition in the Democratic primary, but the entire Democratic ticket was defeated in the general election. In 1911, he ran for state auditor, but lost in the primary to Henry Bosworth. That same year, he was elected as one of Hopkins County's delegates to the state Democratic convention. A bill passed in the state legislature in 1912 created a State Insurance Rating Board under the office of state auditor, and Bosworth appointed Laffoon chairman of the board due to his experience in the insurance field and as a reward for his loyalty to the party. In 1915, Laffoon sought the post of Commonwealth's Attorney for the Fourth Judicial District, which comprised Hopkins, Caldwell, Crittenden, and Livingston counties. He lost in the primary to J. Elliott Baker, but the Republican candidate, Charles Ferguson, won the general election.
In September 1918, Laffoon moved to San Antonio, Texas, where he opened a law practice and managed a citrus fruit business near Galveston. Though he had intended this to be a permanent relocation, while on a visit to family a few months later, friends urged him to return to Kentucky, and he obliged after only three months in Texas. In 1921, he sought election to the bench of the Fourth District Circuit Court. In the primary, he defeated Trice Bennett, a candidate from Princeton, and went on to face Republican incumbent Carl Henderson of Marion. In the general election on November 8, 1921, Laffoon defeated Henderson, carrying every county in the district. In his first term, only 7 percent of his decisions were reversed by the Kentucky Court of Appeals, which was a record for the Fourth District at the time. He was re-elected for a second six-year term in 1927.
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