Lindsey was born on July 4, 1843, in Caroline County. He was the son of John Pendleton and Sally Mickins Pendleton, slaves owned by the Pendleton family. Lindsey and his mother were sold about 1848 to another Caroline County resident. At the age of eleven he was sent to Richmond and hired out as a dining-room servant. Later employed at a female seminary, he learned to read and write, and also how to play the violin and bugle. Lindsey married Eliza McLaine, a slave owned by John Minor Botts, a member of the Convention of 1850–1851 and former member of the, likely by about 1857 when their first child was born. The couple had one son and four daughters, of whom two daughters survived to adulthood.
During the Civil War Lindsey sold newspapers and served as a bugler in the fortifications around. According to a later newspaper article, he was whipped publicly for selling newspapers that he had reportedly skimmed from the publisher to soldiers in nearby camps. He reportedly played music at the governor’s mansion during the Civil War and at the Hot Springs resort after the war, likely bringing him to the attention of politically influential Richmonders. In the spring of 1867 he was a member of the petit jury that was selected for the treason trial, which was never held, of former Confederate States president .
Lindsey became a vocal proponent of black rights and aligned himself with Radical Republican. At a public celebration in April 1867 of the anniversary of the U.S. Army’s entrance into Richmond, Lindsey struck a conciliatory tone when he called for mutual respect between African Americans and whites. At a political meeting of African Americans near Charlottesville on July 2, 1867, however, he called for equality between the races and stressed that the freed slaves should defend themselves, violently if necessary.
Adhering to federal Reconstruction legislation, elections took place in October 1867, for delegates to a convention to draft a new constitution for Virginia. African Americans, eligible to vote for the first time, elected Radicals Lindsey, Hunnicutt,, James Morrissey, and by a margin of 404 votes to represent Richmond at the convention. Lindsey’s fiery rhetoric continued. The Richmond Daily Dispatch reported on November 11, 1867, that in a speech Lindsey demanded “that before any of his children should suffer for food the streets of Richmond should run knee-deep in blood,” warning that African Americans knew how “to use guns, pistols, swords, and ramrods.” He claimed that the newspapers misconstrued his remarks, but Republicans distanced themselves from him. His comments so inflamed the white population of Richmond that he was arrested, though the charges were dropped.
During the constitutional convention, which met from December 3, 1867, to April 17, 1868, Lindsey made numerous speeches and supported the Radical Republicans. He backed Underwood’s election as convention president and advocated employing a stenographer to record convention proceedings. Richmond newspapers ridiculed Lindsey. The Southern Opinion caricatured him as blowing a trumpet to announce Underwood’s election while Cox, Hunnicutt, and Underwood looked on. Editors used his speech, rendered in dialect, as evidence for the need of a stenographer. Appointed to the Committee on the Preamble and Bill of Rights and Division of the Powers of Government, Lindsey requested that a committee ask General John M. Schofield, military governor of Virginia, to remove all presently employed state officials. He also warned that the public would reject any proposed constitution that did not confer equal rights to all Virginians regardless of class or race.
Lindsey presented resolutions to the convention to protect the rights of African Americans in public places and to prevent race from being a factor in prison sentencing. He proposed a clause to exclude from voting or holding office those who had aided the Confederate cause, and he favored disfranchising Virginians who had voted for pro-secession delegates to theand ultimately seceded from the United States. Lindsey also endorsed the test oath, a pledge created to prevent former Confederates from holding state office, which the convention passed. Not surprisingly, he voted against a proposal that favored of African Americans. He opposed segregation in public schools and supported requiring integration, though both clauses were defeated. Lindsey introduced a resolution allowing the exemption of Union soldiers wounded during the war from paying the and another to benefit orphans of soldiers killed in the war. Other proposals included making wage garnishments unlawful without proper notification to the employee and requiring the creation of a paupers’ cemetery in every town and county. He voted with the majority on April 17, 1868, in favor of the constitution. The new state constitution was ratified in July 1869, absent the disfranchisement and test oath clauses.
Lindsey’s career and personal life saw a number of highs and lows following the convention. In January 1869 he was one of eleven Virginians who attended a convention of African American men who gathered in Washington, D.C., to protest the denial of voting and other civil rights guaranteed by the recently passed. Lindsey lost a bid for the House of Delegates in July 1869, but in September he was made a deputy member of the Grand State Council of the Union League of America, a political organization that supported Republican initiatives. In April 1870 he attended a Richmond convention of black workingmen and chaired the committee that offered resolutions endorsing the Colored National Labor Union, calling on laborers to organize, and urging African Americans to remain in Virginia and support the Republicans. Lindsey remained active in the Republican Party during the next decade, serving on local ward committees and the city’s executive central committee and campaigning on behalf of party candidates. A noted speaker, he often appeared on the podium at such events as public celebrations commemorating the . In 1874 he was embroiled in a party struggle over the Republicans’ nominee for Congress and in speeches that autumn he repeatedly implored African Americans not to allow their support to be bought. Lindsey also voiced his fear that the Civil Rights Bill, then being debated in Congress, would result in the destruction of the Republican Party in Virginia.
As a result of his work for the party, Lindsey was awarded the post of janitor at the Richmond customs house in March 1870. When his death was erroneously reported in newspapers in March 1871, the customs house flag was lowered to half-staff. During the next decade, he lost and regained his janitorial post several times, reportedly because of intemperance. Between October 1880 and August 1891 two of his daughters, a grandson, and a granddaughter died, and he was arrested once for assaulting an elderly woman and several times for being drunk in public.
Despite these travails Lindsey still possessed political influence, especially among black voters. In 1880 he was elected president of the Clay Ward Republicans, which passed a resolution supporting the party in spite of calls to align with the Readjuster Party. The Readjusters had won control of the General Assembly the previous year on a platform advocating partial repudiation of the state’s massive public debt in order to fund much-needed public services. In March 1881, however, Lindsey attended a convention of African Americans that adopted a resolution of support for the Readjusters. He employed his renowned speaking skills and political influence on behalf of the new party and its leader, former Confederate general, until the coalition collapsed later in the decade. In 1882, Joseph Jorgensen, a Readjuster congressman from Petersburg, wanted Lindsey’s help in his reelection campaign. He attempted to have Lindsey reinstated as janitor at the customs house, although fellow Readjuster informed Mahone that Lindsey’s intemperate ways disqualified him. Lindsey continued to participate in Republican Party politics into the 1890s, and in 1887 he urged black Republicans to elect to the General Assembly the white Reform Party candidates supported by Richmond’s labor movement, arguing that African Americans would benefit.
In October 1901 he was once again arrested for being drunk in public. The presiding judge recognized Lindsey from his role in the constitutional convention and dismissed the charges. Lindsey died at his home in Richmond from pneumonia on January 4, 1908. He was buried in Evergreen Cemetery. On May 26, 1934, Lindsey was hailed in the Richmond Planet as one of the ten greatest black leaders in Richmond’s history, along with businesswoman Maggie Lena Mitchell Walker and newspaper editor John Mitchell Jr.