Thomas Sully first painted Andrew Jackson in 1824. The hero of the Battle of New Orleans was by then a U.S. senator from Tennessee and a Democratic nominee for president. Sully painted a total of 11 portraits of Jackson, from a head-only likeness to a full-length, life-size image. One of the half-length portraits came into the possession of Francis Preston Blair, Jr., a lawyer, politician, and later U.S. representative and senator from Missouri. Blair was reported to have loaned his Sully painting to Philadelphia publisher George W. Childs, who had Thomas Welch engrave the Jackson portrait. Childs sent complimentary copies of the engraving to prominent individuals, hoping for testimonials that could be published in newspapers to increase sales of the print. Sullys half-length image of Jackson is the most widely recognized portrait of the president; it was the basis for the likeness that appears on the $20 bill.
The Senate owns an oil on canvas painting attributed to Thomas Sully that shares many stylistic similarities to the 1852 Welch engraving, especially in the hair, eyebrows, chin, and facial lines, but differs from Sullys other Jackson portraits. Although Sully may have replicated it from an engraving of his own painting, it is also possible that the Senates oil portrait was copied from Welchs engraving by another, unidentified artist.