Date of Birth: 1479.
Profession: Count, Noble.
Ottaviano entered the service of the Florentine Republic as a condottiero when he was 19, at the request of his mother, Caterina Sforza, who wanted to cement the amiable relations with Florence. He commanded 100 men form Forlì, but terminated his contract after only a year because Florence didn't have the money to pay him.
Despite account which describe Ottaviano as obese, brainless and under his mother's thumb, Pope Alexander VI (Rodrigo Borgia) offered his daughter Lucrezia to Ottaviano. Why? Because Rodrigo decided that those were traits he could tolerate in a son-in-law as long as that son-in-law was the key to controlling the territories of Forlì and Imola. Plus, his praying mantis of a daughter, Lucrezia, rarely stayed married to one man for long. Her husbands tended to sign declarations of impotence or just simply disappeared. Wisely, Caterina denied the marriage, enraging the Pope and leading to his son, Cesare's, assault on Forlì.
When Caterina was ousted by Cesare and entered her exile in Florence, under her guidance Ottaviano attempted to convince the new pope, Julius II, to give him back the lordship of Imola and Forlì, but instead Ottaviano ended up selling the Riario claim to Julius, for an I.O.U. no less.