Praise of this nature led to his being ordered by the Prior General and the Pope to preach a series of sermons in various cities of Italy that competed to hear him.
Giles was reputed to have had blameless morals, but as a preacher and later as Prior General he had to meet men and women of evil repute.
For example, there was Imperia, a famous cortesian. She was mistress of Agostino Chigi, who was a liberal benefactor of the Chigi Chapel (Cappella Chigi) to Santa Maria del Popolo.
This included also Vanozza di Cattanei (1450 – 1511), a papal mistress, who was a devotee of the Augustinian church of Santa Maria del Popolo in Rome. She died in 1511, and was buried in the Costa Chapel (Cappella Costa) there.
In 1503 at Ferrara Giles had met her daughter, the infamous Lucrezia Borgia. Lucrezia was by then the wife of Alfonso d’Este, who was the son and heir of the Prince of Ferrara. It is often suggested that, after her marriage with Alfonso in December 1501, Lucrezia displayed good moral conduct for a number of years. Some credit for this is given to Giles.
During Lent of 1508, Giles undertook the task of preaching to the prostutuites of the city of Rome. According to a contemporary writer, that gave Giles a potential congregation of 6,800 women.
An observer at this sermon by Giles said that he won the enthusuastic attention of his congregation.
He worked such a change that some of them left Rome to return to their families, and others entered religious houses as penitents.
Although his sermon had no major effect on this deeply-rooted practice in Rome, the immediate results nevertheless were a tribute to the common sense and virtuosity of Giles.
Time and again Julius summoned him to preach a sermon or a series of sermons on special occasions, and at two events that he considered of vital importance to his pontificate – the Lateran Council and the concluding of a treaty with the emperor, Maximilian I.
The fame of Giles as a preacher dated from the 1490s. More than once he was called to Rome to preach before Pope Alexander VI. Pope Julius II also had a particularly high regard for him as a preacher.
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