Sheriff Daniel B. Bird (first from the right) was the first sheriff to oversee Monticello’s two-storied brick jailhouse. Even when Florida was a U.S. Territory, Jefferson County residents elected men to help maintain law and order. As an elected official and former city council member, he was among the most influential people in the county.
Lamar Sledge, like all Florida sheriffs, faced constant danger while enforcing the law and keeping the peace. Upon taking office in 1933, he cleaned out the department, dismissing all deputies who served under the previous administration. He spent his first few months strictly enforcing prohibition and traffic laws and chasing down escaped prisoners.
In February 1934, Sheriff Sledge responded to a friend’s plea for help. Ernest Handley came to the jail late one night and requested Sledge and a deputy follow him to his roadhouse in Madison County. Hadley’s wife was missing and he needed help to find her. A few hours later, Handley shot and killed the deputy and fatally wounded the sheriff. In the hospital, Sledge testified that Handley and the deputy had argued, resulting in Ernest using his pistol. He claimed the violence was so unexpected, he never drew his own weapon.
Minnie Cooksey was the first woman to serve as sheriff in Jefferson County. A church organist and mother of three sons, she became sheriff when her husband, J.R. Cooksey, Jr. died in office in 1949. Few women served as sheriffs in Florida, and Mrs. Cooksey was the only female in the state with such at title at that time.
Like Mrs. Cooksey, the governor appointed Alice Lovett to finish her husband’s term after Mr. Lovett passed away. The second of the only two women to serve as sheriff of Jefferson County, neither she nor Sheriff Minnie Cooksey chose to run for reelection. Her successor, J.B. Thomas (right) watches over her shoulder as she accepts her appointment.
As an elected position, politics were an unavoidable part of the sheriff’s daily life. At twenty-five years old, Don Watson was among Florida’s youngest sheriffs ever appointed. He was the fourth sheriff appointed by Governor Claude Kirk in a space of three months following the suspension of Sheriff J.B. Thomas in 1967. He proved to be an apt public official who was eager for change. He petitioned the county to increase his budget to provide raises for his deputies and to hire additional department staff. He joined the board of directors of the Florida Sheriffs Association, and even created a Junior Deputy Program to teach local schoolchildren about laws and law enforcement.
After his landslide victory in the 1968 election, public opinion seemed to turn against Sheriff Watson. In 1971, a grand jury charged him with six misdemeanors and a felony, including possession of a moonshine still. He claimed his political enemies were responsible because of his aggressive attacks on illegal activities. Only a week prior, both his home and independent business were burned by arsonists.