Intermission of the Hundred Years War, prompted by the Treaty of Bretigny in 1360, led to bands of unemployed soldiers released from service who turned to looting and robbing. John Hawkwood traveled to Italy in 1361 as a member of a band of mercenary warriors called "The White Company." By 1365 his military and leadership skills made him commander of this Condottiere. He would become wealthy and famous, selling the services of his mercenary army to various Italian city states.

Sir John Hawkwood died in 1394 in Florence, Italy (never returning to England) where the city provided an elaborate funeral including a painted portrait which remains today in Florence.