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Ottaviano Riario — Description

Ottaviano Riario was a man best described as a living human afterthought. Born on September 1, 1479, Ottaviano was the first son, though second child, of Girolamo Riario, the Count of Forlì, and his smokin’ hot wife, Caterina Sforza, who was nonetheless just an absolutely abysmal mother. By now you all know the story about how Girolamo was a cheap bastard who got himself assassinated in 1488, which then prompted the Papal Army to take the opportunity to try and reclaim Forlì and Imola from their rivals. Caterina locked herself and her children in their quarters during the siege, but they were captured and dragged in front of Ravaldino fortress, used as leverage to try and get the castellan Tommaso Feo to open the gates for the invaders. Feo insisted that he'd only negotiate if he could get a private audience with Caterina inside the fort, and when the Papal Army agreed to this, Caterina appeared on the battlements just moments later to tell the Pope he can go suck her ass. When the invaders threatened to kill her hostage children for this betrayal, Caterina flashed her snatch and proclaimed lmao go ahead bitch, I can always just make more. Luckily, the enemy soldiers couldn't bring themselves to actually slit the kids’ throats, and the invaders were ousted by reinforcements from Milan, but Caterina's flagrant classification of her own fucking children as little more than expendable chess pieces serviceable only to her own political ambitions hits a little too close to home for me, and it's never going to get better.
See, technically, Girolamo's death made Ottaviano the rightful ruler of Forlì, but he was only nine years old at the time and Caterina had been wearing the pants in the family long before the little brats was born anyway. Naturally, Caterina became regent on behalf of her son, but she seemed completely disinterested in letting go of said position any time soon. She had even gotten hitched to Tommaso's brother, Giacomo Feo, entirely in secret just to ensure that the only bargaining chip she had when it came to maintaining her personal control wasn't automatically disqualified. Giacomo, incidentally, was also murdered, in 1495, because he was an abusive despot both to his citizens and his step children, who were little more than another guy's discharge to him. Until Caterina could find a new boy toy to replace Giacomo, she'd finally concede gruffly that fiiiiiine, she'd teach Ottaviano how to actually do anything cause the French are at our doorstep and it's gonna be a big hassle otherwise uuuuuggghh.
Ottaviano's first actually important job as count of a fucking city came in 1498, when he was nineteen years old, as per Caterina's plan to put all of her eggs in Florence's basket. Contracted as a mercenary captain, Ottaviano led 250 soldiers against Pisa, one of the many archnemeses Florence seemingly chose by spinning a wheel every week. While he reportedly did shockingly well for a punk ass kid, he declined to renew his contract after just a year of service, claiming Florence was jilting him on his paycheck. Caterina was not happy to hear that her useless son was trying to drop out of the gig, but talks with Florence took way too long, and bigger problems reared their syphilis-ridden heads. In December 1499, the new Pope Alexander VI's son Cesare besieged Forlì and did what the previous dickhead could not. On January 11th, 1500, Ravaldino's walls were breached, and Caterina was personally violated by Cesare. She was unceremoniously shipped off to Rome and locked in the Vatican's dungeon for eighteen months, before finally breaking and signing away her family's claim to the lordship.
She'd then be exiled to Florence, where several of her children, Ottaviano included, had already escaped to. She was aghast and appalled to find that all of her kids had actually begun settling down and creating their own nest eggs! That wouldn't do! No no no! She'd pumped out these little brats for the express purpose of furthering her own goals and aspirations! In 1503, she dragged Ottaviano out of whatever boring bureaucratic position he'd hooked himself up with and pointed out that hey, they just elected this super anti-Borgia Pope Julius II, there's never gonna be a better time to go stake my- er… I mean your claim to Forlì! Uuuuuggh, fine mom, Jesus, said an exasperated Ottaviano. Supplied with two thousand men by Pope Julius, Ottaviano hauled his fat ass all the way back to middle-of-nowhere Imola and laid siege… to no avail. After being refused entry into the city for so long, Ottaviano just kinda said fuck it, it ain't worth it, and sent his brother Galeazzo in with a giant sack of money to just buy the fucking castle peacefully. The people of Imola then proceeded to take his money and kick them out anyway, and Julius was of absolutely zero help because ehhh it doesn't really matter cause I really wanna be the one in charge afterall, proclaiming Imola and Forlì little more than extensions of the Holy See on November 4th, 1504.
Welp, bemoaned an Ottaviano who'd just had his time completely fucking wasted, fuck me I guess. I fuckin quit. Much to the dismay of his mother, whom Ottaviano had begun to realize was the common denominator in his continued unhappiness and personal fulfillment and should maybe be cut out of his life, Ottaviano retired from military service altogether. Instead, on September 16, 1506, he joined the clergy as Bishop of Viterbo, previously held by his cousin Raffaelle, and for the rest of his days satisfied himself with refurbishing the architecture of his humble little community. He didn't exactly go on to make a mark on history as one of the greatest leaders of his time, but that was also perfectly fine by him. He had something he cared about and he did it humbly right up until his quiet, unremarkable death on October 6, 1523. I get the feeling that the news of his mother's death in Florence in May 1509 elicited little more out of Ottaviano than an “Oh. Is that so? Bummer”. Honestly, more power to you, little man, I'm happy for you.
Design notes, the only historical image verifiably of Ottaviano seems to be a medal struck in his honor during his lifetime, probably to commemorate his service in Florence. I saw it posted that one of the figures in Botticelli's tonda painting, Virgin and Child with Six Angels and Saint John the Baptist, represents Ottaviano, but no citation was given. Still, it had some nice shapes and colors to it that I decided to use as a baseline anyway. Contemporary chronicles remember Ottaviano as fat, dumpy, and a little slow, and… yeah I kinda ended up leaning that way too… but I've developed a lot of sympathy for Caterina's kids and I did my best to portray his portliness in a more fashionable light than even his own medal did. I'm sure a therapist would have a field day dissecting how Caterina would've been the one commissioning the medal and approving the ugly design. You're a great Assassin's Creed character, Caterina, but as a historical person, you're kind of a bitch and I have very little sympathy for you. Be nice to your kids, folks. Otherwise they end up like me, and multiple mes would just be a logistical nightmare for human society at large.