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An unexpected encounter with St. Francis of Assisi in 1213 was to forever change—and enrich—the life of Count Orlando of Chiusi.

On the day a festival was being organized for a huge throng, St. Francis, already well known for his sanctity, delivered a dramatic address on the dangers of worldly pleasures. One of the guests, Orlando (also known as Roland) was so taken by Francis' words that he sought out the saint for advice on how best to lead a life pleasing to God.

A short time later, Francis visited Count Orlando in his own palace, located at the foot of Mount La Verna. Francis spoke again of the dangers of a life of wealth and comfort. The words prompted Orlando to rearrange his life entirely according to the principles outlined by Francis. Furthermore, he resolved to share his wealth by placing at Francis' disposal all of Mount La Verna, which belonged to Orlando. Francis, who found the mountain's wooded recesses and many caves and ravines especially suitable for quiet prayer, gratefully accepted the offer. Orlando immediately had a convent as well as a church built there; later, many chapels were added. In 1224, two years before the death of Francis, Mount La Verna was the location where Francis received the holy wounds of Christ.

In return for his generous gift, Orlando desired only to be received into the Third Order and to have St. Francis as his spiritual director. Under Francis' guidance, Orlando completely detached himself from worldly goods. He zealously performed acts of charity as a Christian nobleman. After his happy death Orlando was laid to rest in the convent church on Mount La Verna.