 Hawkwood had a long military career and a complicated relationship with Florence . He fought for England during the Hundred Years War and then with the " Great Company " which had harassed the Avignon Papacy . After gaining command of the " White Company " from Albert Sterz in the 1360s , Hawkwood led the company across the Alps in 1363 in the employ of John II , Marquess of Montferrat , to take part in his war against Milan . Hawkwood and the " White Company " remained in Italy , accepting money from many city @-@ states , both to wage war and to refrain from it . Hawkwood 's reputation as one of the ablest condottieri in the peninsula developed in the ensuing decades , during which he was employed ( by both sides ) in the Pisan – Florentine War ( 1363 – 1364 ) , notably winning the Battle of Cascina ( 1364 ) for Florence , in the wars of Perugia against the Pope ( 1369 ) , and in the service of Bernabò Visconti in his war against a coalition that included Pisa and Florence , and even ( in 1372 ) the Marquis of Monteferrato . 
