Robert H. Whittaker was born probably into slavery, possibly as early as 1830 or as late as 1845 based on his age as recorded in the census records between 1870 and 1900, and probably in Brunswick County. Reliable information about his personal life is extremely scarce and the circumstances of when and how he became free are unknown. References to him in the county’s deed books, including transcriptions of his signature, and in one chancery court case nearly all show his surname spelled with a double t, but newspaper stories, census returns, and legislative and other public records inconsistently spell it with one or two. Whittaker may have been married to a woman named Mary, surname unknown, before the American Civil War (1861–1865), with whom a Robert Whittaker was recorded as living with two sons by the census enumerator in 1870. Whittaker’s wife apparently died during the 1870s because in 1880 the census enumerator recorded him as boarding alone in the household of a friend.
When and under what circumstances Whittaker entered politics are not clear. Few copies of Brunswick County newspapers survive and regional newspapers seldom reported on political events in the county. His earliest known political activity was winning election in May 1871 as a justice of the peace for the county’s Totaro Magisterial District. In August 1873 the Republican Party committee in Brunswick County nominated Whittaker for the county’s seat in the House of Delegates. During the campaign a newspaper described him as a Radical Republican. In November 1873, Whittaker won election to the first of two consecutive two-year terms by defeating a white Conservative, 1,448 to 961. A man identified as a chronic campaigner announced early in the next year that he would challenge Whittaker’s eligibility to serve in the assembly “on the ground that he is ignorant and incapable of performing the duties that would devolve upon him as a legislator.” The journal of the House of Delegates does not record the receipt of a challenge. Whittaker was appointed to a low-ranking seat on the relatively unimportant Committee on Public Property. He introduced a bill to permit a referendum in some districts in the county on whether to enforce the state’s fence law, but the bill did not pass.
During the congressional campaign in 1874, Whittaker called for the election of an African American to the House of Representatives from his district. A newspaper account of his speech on the occasion reported, “This county, he said, was a black man’s county, and he was in favor of sending a black man to Congress.” During the second session of his first term in the assembly, Whittaker voted in March 1875 against a proposed amendment to the state constitution that, among numerous other things, introduced payment of a poll tax as a prerequisite for the suffrage to discourage poor African Americans from voting. Voters ratified the amendment in 1876.
Whittaker attended a state convention that met in August 1875 to discuss the economic inequalities faced by African Americans in Virginia and in November of that year won reelection by defeating another white Conservative by a vote of 1,227 to 827. Whittaker introduced a bill to repeal the fence law in Totaro and Red Oak Magisterial Districts in the county, but like his 1874 bill, it did not pass. In February 1876, while the General Assembly was in session, he attended and spoke at a meeting of African Americans who proposed to establish an industrial school in Richmond. Local Republicans nominated Whittaker for a third term in the House of Delegates in October 1877, but he must have declined to run since his name is not listed as a candidate in official election returns that year.
It is uncertain whether Whittaker remained active in local politics in the years immediately after he retired from the General Assembly. He attended the March 1881 convention of African American Republicans in Petersburg that voted to affiliate with the new biracial Readjuster Party that proposed to refinance the pre–Civil War public debt in order to reduce the cost of debt service so as to be able to increase appropriations for the public schools.
About 1884, Whittaker married Minerva Ann, maiden name unknown. They had one child who died young. It is unclear when he first acquired land. An 1897 deed reveals that he had purchased 2.9 acres of land near Union Church by a deed that was never registered and on a date not disclosed. The county’s deed books and land tax records preserve no evidence that he purchased land before January 1884, when he borrowed money to pay a debt by mortgaging the twenty acres of land where he then resided together with the crop of winter wheat he had sown. If he did not yet own the land but merely rented it, his taking out a mortgage on it was not strictly legal, although he and the man who held the mortgage may have understood that the mortgage applied only to the crop of wheat, which was within Whittaker’s legal right to use as collateral on a loan. Whittaker paid off the loan in 1887 and in February of that year bought 22.4 acres of land (adjacent to the 2.9-acre tract) for $150. Whittaker and his second wife lived there, about three miles southwest of Lawrenceville, but never owned more than about thirty acres of land. Census enumerators identified him as a farm laborer in 1880 and as a farmer in 1900.
In May 1887 Whittaker won election to the first of three consecutive two-year terms on the Brunswick County Board of Supervisors from Totaro Magisterial District. By the time his third term concluded at the end of June 1893 he had begun to have serious financial troubles. His earnings from his small farm could scarcely have made him financially secure. In November of that year he and his wife mortgaged “one black female mule (Eliza)” to pay a $99 debt, and in April 1894 they sold for $20 each two two-acre portions of their farm. After creditors sued them in 1895, they were unable to rent out their property for enough to cover their debts, and in the autumn of 1897 they mortgaged all the land that they then owned (the tract of 22.4 acres and the adjoining one of 2.9 acres) and “one bay mare called Sallie” to cover all the debts. With accrued unpaid interest the two debts then stood at $51.78 and $17.91. They were unable to pay either the principal or the interest, which continued to accrue, and the court of chancery ordered that all the Whittakers’ land be sold at public auction. The property sold in September 1902 for $150.
Whittaker worked as a letter carrier during the last decade of his life and was living with a friend in or near Lawrenceville when he died on September 7, 1905. The place of his burial is not recorded.