Rainey was elected sheriff in November, 1963. In campaign speeches he told listeners he was "the man who can cope with situations that might arise." Given the rising racial tensions and Rainey's reputation for being tough on blacks, there was little doubt what sort of "situations" Rainey was referring to.
Rainey was a born and raised in Neshoba County. He attended school through the eighth grade, then found work as a mechanic before entering law enforcement. In October, 1959, working as a Philadelphia, Mississippi police officer, Rainey shot and killed a black man from Chicago as he was complying with Rainey's order to get out of his car. No charges against Rainey grew out of the incident. His reputation for brutality grew. In one particularly vicious incident, Rainey participated in the whipping with a heavy leather belt of a black who had been stripped naked.
To those who were white and neither labor organizers or civil rights workers, Rainey was downright friendly. According to one Rainey supporter, "He had a grin, a wave, and a good word for every friend he met." The gregarious sheriff wore a Stetson hat, cowboy boots, and a loaded six-shooter as he wielded his considerable discretionary power in Neshoba County.
On June 21, 1964, at the time of the civil rights workers' arrests, Rainey was in Meridian visiting his sick wife at the hospital. Although he stopped at the courthouse around 8 p.m. that evening, it is not clear that he learned of the civil rights workers arrest and later release until he talked to Deputy Sheriff Cecil Price at the jail sometime after midnight. According to Rainey, Price told him that the three had been released about 10:30 p.m. What is highly likely, given the close relationship between the sheriff and his deputy and their common hatred of civil rights workers, is that in that meeting Rainey was told in detail of the successful execution of the conspiracy to murder Schwerner, Goodman, and Chaney. It is, of course, quite possible that Rainey was himself involved in the conspiracy, although this was not proven successfully at trial.
Following his arrest on conspiracy charges, Rainey became a virtual folk hero to local whites. He received applause, pats on the back, gifts, and even was sought to endorse products and services ranging from chewing tobacco to chiropractic back pain treatments.
Rainey's term as sheriff ended in November, 1967. After his trial, Rainey was unable to find employment in law enforcement. He accepted work as a security guard first at a supermarket, then at the Meridian Mall. Rainey complained in the mid-seventies, "The FBI set out to break me of everything l had, then keep me down where I could never get another start, and they done it."
Rainey suffered from throat cancer and tongue cancer. He died on November 8, 2002 at age 79.