Charles the Bold, born on November 10, 1433, was the son of Philip the Good, Duke of Burgundy, and Isabella of Portugal. He held the title of Count of Charolais until his father's death in 1467, at which time he succeeded him as Duke. Ambitious to enlarge his domain, his actions sparked the Burgundian Wars in 1474, but he was handed three major defeats by the Swiss in 1476 and at Nancy in 1477. It was at the Battle of Nancy, on January 5, 1477, that Charles was killed, his mutilated body not being discovered for several days. With his sole heir being his daughter Maria, Charles was the last of the Valois Burgundy dukes, and the duchy was split between the French crown and Habsburg archduke Maximilian I of Austria, who married Maria in August of 1477.

This medal was probably issued at the time of the siege of Neuss in 1474. The ram on the reverse refers to the Order of the Golden Fleece, which was established by Charles's father. Charles was made of a Knight of the Golden Fleece when he was but twenty days old. The inscription above and below the ram is the joint motto of Charles and his third wife, Margaret of York.

This medal and three others of similar style form a distinct group produced at the Burgundian court between 1472 and 1480. Giovanni Candida has been suggested as the most probable artist behind this group. However, they all feature portrait heads on a scale larger than that in all other works by Candida. Barring this attribution, it is possible they could belong to the oeuvre of an unidentified Burgundian medalist.