John Wayles Jefferson (né Hemings) was a grandson of the slave Sally Hemings (1773 – 1835) and thus has been considered to be a grandson of President Thomas Jefferson (1743 – 1826), although this has not been conclusively established. Never officially acknowledged but freed in Thomas Jefferson’s will, this mixed-race family had deep white European roots. In the nineteenth century, they moved from Virginia to Ohio and eventually to Madison, Wisconsin in 1852, the year Congress passed the Fugitive Slave Act, which threatened the status of free Black men and women.

By 1860, John Wayles Jefferson (1835 – 1917) was operating Madison’s American House hotel located on Capitol Square and presenting himself as a white man. In September 1861, he enlisted in the 8th Wisconsin Infantry. With the so-called Eagle Regiment, he took part in forty-one engagements, sustaining injuries at Corinth and Vicksburg, before being mustered out of service in October 1864 with the rank of colonel.

Colonel Jefferson’s portrait was painted by Alexander Marquis in 1874. Born and trained as a painter in Glasgow, the Scottish artist came to Wisconsin around 1850. He hung out his shingle in Milwaukee as a portrait painter and teacher of drawing. Marquis’s portrait style drew heavily on the work of a Scottish predecessor, Sir Henry Raeburn, who had established a reputation for a telling likeness with strongly lit facial features and a neutral background that often appealed more to men than women. Before relocating to Denver in the early 1880s, Marquis painted some three hundred portraits and tutored the next generation of the Milwaukee artists.