In 1376, Archbishop Pileo was drawn into the expansionist military adventures of Barnabò Visconti of Milan, who threatened Tuscany as well as territories belonging to the papacy, including Bologna and the Patrimony of S. Peter. The archbishop was ordered by Pope Gregory to support his Cardinal Legate in Bologna and the Marchese d'Este with the sum of 500 gold florins charged against the archbishop's income as bishop. The raising of the required sums brought the archbishop a bad reputation as a despoiler of church property. At the same time, a Ghibelline rebellion in Ravenna cut the archbishop off from his source of income.
