The War of the Eight Saints (1375–1378) was a war between Pope Gregory XI and a coalition of Italian city-states led by Florence, which contributed to the end of the Avignon Papacy (67 years during which seven successive popes resided in Avignon - part of the Holy Roman Empire, now in France - rather than in Rome).

Many Florentines feared that the pope would turn his military attention toward Tuscany; thus, Florence paid off Gregory XI's main military commander, English condottiere John Hawkwood, with 130,000 florins to not to make war in Tuscany, limiting himself and The White Company to putting down the various rebellions within the papal states. In 1377 Hawkwood abandoned Pope Gregory XI entirely and joined the anti-papal coalition.

The funds for Hawkwood’s pay-off were extracted from a the clergy of Florence by a special commission of eight citizens (The Eight Saints or Otto Santi) in the form a one-year, forced loan.

John Hawkwood earned command of The White Company (also known as the Great Company) in 1365 by election. The company was a 14th-century Italian mercenary Company of Adventure consisting of thousands of cavalry and infantry, particularly English longbowmen who were sometimes mounted on horseback. The company was organized into lances of three men; a man-at-arms, a squire and a page. Of these, only the man-at-arms and squire were armed.

The White Company is credited with introducing to Italy the practice of dismounting men-at-arms in battle, a practice already commonplace in the battles of the Hundred Years' War in France. Contemporary witnesses record that the Company fought dismounted and in close order, advancing with two men-at-arms holding the same lance at a slow pace while shouting loud battle cries. The longbowmen apparently drew up behind. This is not to suggest that they abandoned mounted combat altogether.