Nannie Cox Jackson

Nannie Cox Jackson (February 26, 1865 – September 19, 1953) was a prominent African-American educator, wealthy property owner and businesswoman in Charlottesville, Virginia.

In addition to her career as an educator, Jackson is notable for being one of the most substantial African-American landowners in Charlottesville, Virginia, as well as owner of one of the first African-American billboard companies in the United States, Jackson Advertising.

Early life, family, education, Thomas Jefferson genealogy Jackson was born on February 26, 1865, in Charlottesville, Virginia. She was the daughter of Elizabeth Scott (February 19, 1824 – July 15, 1916) and Elizabeth's married enslaver, Dr. William Cox (October 29, 1808 – April 15, 1875).

Jackson' maternal grandmother, Nancy Colbert Scott (1810–1864), was Elizabeth Scott's mother. Nancy Colbert Scott's parents were Burwell Colbert (December 24, 1783 – 1862) and Critta Hemings Colbert (1783–1819). Burwell Colbert was the third President of the United States Thomas Jefferson's enslaved manservant and Monticello estate's butler. Critta Hemings Colbert was the niece of the famed Sally Hemings, President Jefferson's documented, enslaved African American concubine.

After President Jefferson's death in 1826, the Jefferson Estate had accumulated extraordinary financial debts, upwards of $107,000 — more than $2,934,316.80 in 2021 dollars. Much of this debt was attributed to multiple factors: the Panic of 1819, insufficient income from the Monticello's agricultural holdings, and, notably, Jefferson's extensive travel expenses, excessive lifestyle and imprudent financial decisions.

In 1842, Garrett resold Nancy Colbert Scott to her eventual husband, Robert Scott, whom she had nine children. Thomas Jefferson Randolph later sold his enslaved daughter to the wealthy Garrett family of Charlottesville, Virginia. Dr. William Cox had six children with his Mary Elizabeth Lacy Cox, rendering these children Jackson's half-brothers and sisters: Eugene Montraville Cox (1833–1885), Lucian Napoleon Cox (1835–1862), Adelaide Panthea Cox Comer (1836–1899), Almira Josephine Cox (1840–1927), Azell Donop Cox (1842–1913), and Leroy Wesley Cox (1845–1938). According to Jackson's descendants, Dr. Cox would send children Leroy Wesley and Azell Donop to spy on his involuntary mistress' children to ensure that they were behaving. W. E. Jackson stayed active with the Republican Party until 1922 when state party Republicans racially denied W. E. Jackson and other elected African-American delegates a seat at the State Republican convention in Luray, Virginia.

The Jacksons had five children: W. E. Jackson, Charles Leland Jackson, Helen Elizabeth Jackson, Nannie Gladys Duncan, and Marion Louise Carter. The Jackson Family were considered one of Charlottesville's preeminent African American middle-class families, known as the "Four Hundreds Club". Charlottesville locals believed that after African Americans were emancipated in 1865, several African-American families made a pact to obtain education, own businesses or obtain well-paying teaching and school administration jobs, and buy land. Each plot of land generally costed $400, hence the ""Four Hundreds Club." In addition to the Jackson family, the "Four Hundreds Club" included the Coles, Bells (owner of the J.F. Bell Funeral Home), Tonslers, and Inges families. Instead, Jackson would take her training to empower her students to live independently, self-sufficiently and with stability. Jackson also organized and subsidized school's lunch program, though the Charlottesville School Board approved it but did not co-finance it. Organizer of the Jefferson School (Charlottesville, Virginia)'s first ever football team, Jackson was well known for recruiting the football coach, and feeding the school's football players and coaches after each game. Operating out of their home at 204 Sixth Street NW in Charlottesville, Virginia, the company began as "Cox Poster Advertising", a company initially owned and operated by Nannie Cox Jackson's brother, James Rinaldo Cox. She was interred at Oakwood Cemetery in Charlottesville. At the time of her death, Jackson's estate was worth well over $1,000,000.