Leonard R. Flemings was the son of Charles Flemings and Mary Flemings. He was born free in Lancaster County sometime between 1857 and early in 1861 according to what census enumerators recorded between 1860 and 1930. Flemings may have believed that he was born about January 1861, which is the date he provided the census enumerator in 1900 and that roughly agrees with his age as recorded when he first married and his age as given in a deposition in 1895, but at the time of his death a daughter stated that he was seventy-six years and eight months old, suggesting a birth date about August 1860. His first name appears once in the county records as Lemuel, and the family surname appears as Fleming and as Flemings in the local records, but he signed his name L. R. Flemings.
On March 11, 1883, Flemings, who was keeping a store, married Sarah Jane Griffin, of Lancaster County. They had thirteen children (including one set of twins) before her death on January 13, 1910. Three sons and three daughters were still living at the time she died. Sometime during the 1910s, Flemings married a woman named Alice, but extant records do not disclose her maiden name, when they married, or when she died. The 1930 census listed Flemings as living alone and owning and operating a retail grocery. During part of his life Flemings had an unspecified interest in oyster harvesting or marketing and in 1904 won election to the board of the newly created Lancaster County chapter of the Oystermen’s Protective Union.
Beginning at the end of the nineteenth century he alone or with other men managed the county Afro-American Fair that was often held on his property until about 1911. The event was revived in 1927 when African Americans were banned from attending the county’s Chesapeake Fair. Flemings served as manager of the exposition, which was held at a new location. He and members of his family were active in the Queen Esther Baptist Church. In 1908, on the first anniversary of his mother-in-law’s death, he published in the local newspaper an eloquent tribute to her and her faith.
Local public records suggest little that was remarkable about Flemings’s private life. His more remarkable public life is somewhat better, though still poorly, documented. About 1887 he became a justice of the peace in Lancaster County. By then justices heard minor civil and petty criminal cases and no longer presided over courts of record, so original documents concerning his service are scarce. But items that he signed were copied into the county’s official records often enough to demonstrate that Flemings served continuously—he was reelected every fourth year—for at least thirty-two years.
In spite of the provisions of the Constitution of 1902 and the revised election laws adopted during the ensuing session of the General Assembly that were explicitly designed to deprive African Americans of the vote and to keep them out of public office, Flemings continued to be reelected to his post as justice of the peace as late as 1915. His name disappears from rosters of state magistrates published between 1919 and 1927, but it is possible that he remained in office. In 1912 Flemings had been named a registrar of vital statistics in his magisterial district by virtue of his post as a justice and he continued to serve as a registrar for more than a decade. Elected a justice of the peace again in 1927, Flemings was reelected two more times and was still in office at the time of his death. He was also coroner in his district early in the twentieth century and in 1908 and perhaps on other occasions sat on the county’s grand jury. In 1896 Flemings served as secretary of the Republican Party’s First Congressional District convention and was also a delegate to the party’s state convention that year.
Flemings was almost certainly the longest-serving black public official in Virginia’s history prior to the Voting Rights Act of 1965. If he served through the 1919–1927 period when his name is not included in published lists of magistrates, he was a justice of the peace for about a half century, and even if not, he very likely held office longer than any other African American during the first decades of the twentieth century. Flemings’s unusual career, which is the exception that proves the rule, may be explained by circumstances particular to the locality.
Lancaster County had a black majority when Flemings entered politics, and in spite of aout of racially segregated Virginia during the early decades of the twentieth century, it remained a majority-black county into the 1920s. Illiteracy among African American adults in the county was very high, which made voter registration difficult after 1902, but numerous black men (and after 1920 a few ) in the county nevertheless managed to register. According to a local newspaper, in 1927 almost one-quarter of the registered voters in Flemings’s White Chapel Magisterial District were black, proportionately more than in any other district in the county. The state did not compile or publish voter registration figures giving racial identifications, but that figure was probably uncommonly high, and black voters continued to register in large numbers during the 1930s in Lancaster and two neighboring counties. Elections for justices of the peace may have been regarded as nonpartisan, and in a district with a large black population and a significant number of black voters, local white political leaders may have deemed it in their interest to have a respectable property-owning black man serve as one of the magistrates.
Unfortunately, the local weekly newspapers did not report or comment on the relatively unnewsworthy campaigns for justice of the peace, nor did they report on what might have been regarded as shocking news elsewhere in Virginia, that an African American man repeatedly won election. Flemings was not identified as African American in the occasional newspaper reports of his being elected or in the state’s lists of magistrates, even though his name appeared in the newspapers in other contexts that clearly indicated his race. That suggests that locally his elections were not regarded as remarkable, but it inadvertently concealed from white Virginians elsewhere and from historians and political scientists later that a black man repeatedly won elections in the state during a time when all black men were believed to have been effectively excluded from public office.
Flemings died at his home in Mollusk, of arteriosclerosis and myocarditis, an inflammation of the heart, on April 6, 1937, and was buried in a nearby private cemetery. The Kilmarnock Rappahannock Record printed a notice of his death and an account of his funeral and characterized him as “a noteworthy citizen and justice of the peace for a number of years.”