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.