Serving Italian factions
Hawkwood and his company arrived in Italy during the power vacuum following the Great Schism of the papacy, and many different political figures were vying for power. The Pisan–Florentine War was the beginning of Hawkwood's military career there, as he assumed command of the Pisan army in the winter of 1364–65, at the age of almost forty. The Battle of Cascina determined the war. Before the war, John Hawkwood and the Pisan army had met at Malatesta. Hawkwood's tactics in this battle are what distinguished him as a military commander, even though he lost it. He took account of the terrain and conditions of the battlefield and positioned his army accordingly. However, the turning point came when the opposing commander ordered an enveloping move that cut Hawkwood off from the rest of his army. Hawkwood ordered his army to retreat. The modern perception of the battle is romanticised, as it is claimed as a heroic stand against great odds. Yet the defeat is likely to have been due to young, undisciplined soldiers fighting on Hawkwood's side.
The second telling battle in Hawkwood's career was Rubiera on 2 June 1372, fought between papal forces and Bernabò Visconti. Both sides had concluded a formal truce, but in reality, they were gathering more troops. Hawkwood and Visconti commanded a force of a thousand lancers with no infantry. The papal forces were larger: 1,200 lancers as well as infantry. Hawkwood outflanked and outmanoeuvred his enemy and took most of the high-ranking officers captive. The victory shows Hawkwood's ability as a commander, although it had no significant political results and ended in a truce between the Visconti and the Pope.
One of Hawkwood's more important roles was in the Great Raid on Tuscany, which shows the connections of the condottiere and the political prosperity of the Italian states. The raid led directly to war between Florence and Gregory XI and boosted Hawkwood's career in fame and wealth. Frustrated by not being paid by the Pope, Hawkwood marched along the Via Emilia towards Tuscany and Florence. Two Tuscan ambassadors met him to conclude a truce, for which they paid him 130,000 florins. He continued to march through various territories, such as Pisa, Siena and Arezzo, where he continually pressed for money. Many believed these raids were under orders from the Pope, and so they led to a defensive league between Florence and Milan. Siena, Pisa, Lucca, Arezzo and Queen Joanna I of Naples soon followed and joined the defensive league against the company and the Pope. No matter who was responsible for the raid, Hawkwood's raid proved the casus belli, which eventually led to the War of Eight Saints.
In the War of Eight Saints in 1375, Hawkwood and his company began fighting for Pope Gregory XI against Florence. In December, he went to Città di Castello on orders to put down a rebellion, but ended up capturing the city, which was not what the frustrated Pope had intended, but Hawkwood did so in an attempt to extract payment from the Pope. As a result, Gregory "had little choice but to formally invest him with it, in return for uncompensated services." After capturing Città di Castello, Hawkwood rode to Faenza on 12 February 1376, on orders from the papal governor for protection because he feared revolt. While at Faenza, Hawkwood attempted to lay siege to the neighbouring town of Granarola, but was forced to retreat to Faenza. The papal governor allowed John Hawkwood and his men into the town, expecting them to defend it for the Pope. Once inside, Hawkwood ordered the townspeople to hand over their weapons. However, because the Pope had not paid his soldiers, Hawkwood’s troops looted the town instead of protecting it. When Florence, the Pope’s enemy, learned of this, they took advantage of the situation: they bribed Hawkwood to stay out of the fighting, promised him a regular pension, and forgave all the betrayals and wrongdoings he had previously committed against Florence.. Yet Hawkwood remained with the Pope. Later he took part in the Massacre at Cesena, to which he was called to help enforce a decree promising forgiveness to citizens who laid down their arms. Thus Hawkwood and his men joined in the attack on the unarmed civilians. This was a turning point in Hawkwood's career, after which he left papal service and began working with Milan, Florence and their allies.
Hawkwood would eventually sign a contract with Florence after a quarrel with his father-in-law, Bernabò Visconti. After winning a battle against John Horvatí, Hawkwood and Lutz Landau crossed paths with Horvatí and stole some prey from his hunt. Bernabò was unsettled with this, and consequently stripped Hawkwood of Milanese land received in his wife's dowry. Thereafter Florence hired Hawkwood, the Landau brothers and their company for eight months, but the contract lasted much longer.