A Most Beautiful Deception

By Insomniac Owl


A/N: The history behind this is complicated, and there are whole chapters of many books written about this New Year's Eve in 1502. The simplest version is that a handful of Cesare's mercenary captains - condottieri in Italian - thought Cesare was getting too greedy; some of their territories bordered the Romagna, Cesare's new state, and they were afraid that once he subdued those lands he would turn an eye to their territories too. They met together, made plans, openly defected, but ultimately couldn't decide to do anything fast enough. Cesare had broken them up from the inside, his formidable reputation convincing one of the group members to turn, and setting the rest against each other. He then had them sign an agreement swearing their renewed loyalty to him, in turn promising he would take no revenge. A month or so later these captains subdued Sinigaglia, and told Cesare that the castellan (who may or may not have been in league with the condottieri in another plot to assassinate Cesare) would only surrender to the duke in person, so Cesare came. This is what happened.


It is snowing, and the horses have some trouble reaching Sinigaglia at all. Cesare sent two hundred cavalry ahead of the main troops, but they've been moving so slowly that by now Micheletto can see the last of them as they crest each new hill. It doesn't matter. Two days ago he rode to Sinigaglia to make arrangements for their arrival; he knows they are only a few miles out now. But in the meantime he must find Cesare. Miniature snow drifts have gathered on everyone's shoulders, and it is difficult, even though Micheletto knows where he is riding. In the end he must look for Cesare's horse instead - a big black Venetian courser that is considerably easier to find.

He urges his own mount forward, finally pulling up at Cesare's side. "My lord," he says. "Everything is in place."

Cesare turns toward him. His hood is pulled low against the wind and snow, and something about it reminds Micheletto of the crimson hood Cesare wore as a Cardinal. But those days are long over; Cesare has made sure of that. This cloak is black, not red, and a Cardinal does not lead an army or murder his brother or plan a massacre. Under this cloak, Cesare's eyes are as hard and sharp as the sword he wears at his side.

Cesare turns in the saddle to look over the column of men behind them, and Micheletto glances briefly back as well. To the left the Adriatic is grey and infinite; to the right, mountains slope toward the sky, bare trees poking up from snow drifts like old crosses. A gust of wind blows the hood back from Cesare's face, and he lifts a hand to steady it. "You're sure?" he asks. "Everything must be perfect, Micheletto."

"Colonna knows his task, as do the others. We should reach Sinigaglia within the hour."

"Have a rider sent out to announce our arrival. Tell them I would have them meet me just across the bridge. Have their troops left the city?"

"They were moving out when I met with Oliverotto two days ago. They should be gone by now, but I will tell the messenger to make sure of it when he is there."

"Good. Good." Cesare smiles then, suddenly, the expression sharp and white against the black of his hair and cloak. "This is a day for vengeance, Micheletto."

"Would that it were not so cold."

He laughs. "Indeed, the fires of hell should burn today. But their horses can ride through snow no faster than ours, and everything else has been accounted for. The house is as I said?"

"Yes. I can lead us to it, if you like, but it is not difficult to find."

Cesare nods, turning back toward Sinigaglia, which Micheletto can see emerging from the distance. It will not be long now. He can make out the hazy shapes of their troops, and the long line of the river, then the wall, then the ramparts of the castle of Sinigaglia on the hill. He's forgotten who it belongs to, which family made their home here in this once-glorious city, but it matters little. They are gone now, fled in fear of Cesare's army when he first swept through this land two years ago, and their city is Cesare's to do with what he will.

The snow comes down in thick, wet flakes, sticking in Micheletto's hair and beard. His beard is soon crusted in a thin layer of ice, but by then he can see the city, rising from behind a hill perhaps half a league away. And just before the bridge, as planned, waits the first two hundred cavalry. Micheletto looks at his master and sees the shape of what will happen here today in the set of his mouth and jaw, in the burning too-early triumph in his eyes, and if it were in him to be afraid of such things, he would be fear his master now. Instead he urges his horse closer. "My lord," he says.

Cesare looks up, sees the cavalry waiting. They stand in two equal rows, a hundred facing the river, a hundred the country they have ridden out of, but as Cesare approaches every eye turns toward him. "This is only the beginning Micheletto," he says, as they pass between the ranks. A cold wind pulls at the edges of their cloaks, blowing snow into their faces, but Micheletto does not turn his head against it because he can see Vitellozzo just across the bridge. He can see Pagolo, and Gravina Orsini. He closes a hand around the hilt of his sword.

Their mules are small and ill-shapen beside Cesare's courser; even Micheletto's more humble mare makes the animals look small, and the men beside them weak. But Cesare dismounts to meet them, and hugs each as though they were a brother.

"Vitellozzo, my friend, you seem sad," Cesare says, putting the man at arm's length. Vitellozzo wears a green cloak wrapped securely about his shoulders, and he seems more ill then anything else, his face wan and pale in the winter sun.

"No, my lord," Vitellozzo says. "I am overjoyed to meet you once more as a friend, as are your other loyal captains." He looks sad then, Micheletto thinks, and maybe what he says next is true, or as near to truth as the man can get. "I wish we I had never turned against you, my lord. It was unseemly, for you are as a brother to me."

"And you to me," Cesare says, clapping him on the back. "But where is our brother Oliverotto? I do not see him here.

"Oliverotto awaits you in his own apartments, my lord," Vitellozzo says, turning back toward his mule. "He begs your pardon, but he is not well enough to come out to greet you."

Cesare turns toward Micheletto, the curve of his hood hiding his face from the Vitellozzo and the others. He says nothing, but Micheletto nods, because Oliverotto is his responsibility, the way Vitellozzo is Monseigneur d'Enna's, and the others Cesare's remaining faithful captains. This is part of the plan, that all the men are together. As Cesare and the others start into the city, Micheletto spurs his horse on ahead.

He finds Oliverotto where he had been two days before, in his apartments overlooking the main square, but there are troops out in the square now, men in boiled leather who turn to watch him as he rides past. If they make him nervous, he does not show it. He sees a face in one of the upper windows, and then a boy is stepping out from around the side of the house.

"I would see your master," Micheletto tells him as the boy reaches for the horse's reins. "Tell him his lord, the most illustrious Duke Cesare Borgia, has missed him at the gate."

A girl shows him into the house, leading him to the receiving room. There is a view of the square outside, of the soldiers in boiled leather and Oliverotto's colors. Micheletto eases one shoulder back against the wall, staring down at them. These men were supposed to have been gone by now. They were supposed to have been gone two days ago.

He hears Oliverotto coming down the hall then, and looks up to see him sweep into the room, in wools and a heavy cloak because even indoors, with fires burning in the grates, it is cold here. "Micheletto," Oliverotto says. He fingers the clasp of his cloak with one hand. "I am unwell; I regret I could not meet the Duke in person, but - "

"If your troops stay too long in the square," Micheletto says, "they will have nowhere to stay. The Duke's own men have already come into the city, and are looking for accommodations of their own."

Oliverotto glances out the window, and then back at Micheletto, then back out the window. "You're right, of course. I will have word sent for them to go indoors."

"Perhaps you should do that now, and then come with me to meet il Valentino. He would be very pleased to see you, I know."

"Ah," Oliverotto says. "Surely, though, the Duke understands that I am ill?" But that is a lie; Micheletto can see just by looking at the man that he is not ill. There is good color in his face, and he makes small, rocking movements on the balls of his feet, as though he wants to run for the door.

Micheletto smiles. "You need not stay long."

So Micheletto waits, leaning outside the bedroom door as Oliverotto dresses, and he listens without hearing as Oliverotto talks at him during the ride - about the hunting in the area, and how faithful he is to Cesare, and how much he has always admired Micheletto's skill with a sword. Cesare hails them as they approach, and Micheletto takes his place at his master's side. Oliverotto is left to fall in with the other condottieri.

The house is close, and it is not long they dismount before it, Cesare's boy moving forward to take both their horses. The house is modest. It has two stories, and more rooms than most, but it is not the castle on the hill or even the villa Micheletto saw on the way in, past the city to the south. But they will not stay here long, and anyway it is the layout that is important. Cesare had been very clear on that point. It must have a central meeting room, with a smaller chamber, large enough to accommodate the thirteen of them here but not much else.

Stepping into the meeting room, already laid out with a table and chairs, Micheletto drifts toward the back of the room, behind the end of the table. Cesare's place. There is a chair for him at his master's right, but Micheletto is more comfortable standing. The other condottieri sit, Oliverotto fidgeting under his gaze, but Micheletto pays him little mind. Cesare is speaking. Words of welcome, friendly, comforting words; he references the treaty signed and promises again to uphold his side of the deal, to protect them from their enemies, to forgive them their betrayal. Micheletto lets his body settle into silence against the cold stone at his back, one hand reaching up to grip his doublet. Cesare's voice is honey and velvet, as smooth as lies. Outside, the snow keeps falling.

The four condottieri are settling, reassured by Cesare's words and his easy posture at the head of the table. Even Oliverotto has calmed. None of them have made a move toward their weapons and, nodding once to himself, Micheletto reaches forward to touch Cesare's shoulder.

Cesare turns. He has thrown his hood back, and his eyes are dark but warm, too, despite the chill. "You must excuse me, friends," he says. The velvet of his cloak drags gently over his chair as he rises. "I will be but a moment. I will have wine sent in, in the meantime. Please." He nods to the men seated at the table, as charming here as he ever was at the court of France, then turns to lay a hand on Micheletto's arm.

He leans in suddenly, close enough that Micheletto can feel his warmth. "Don't kill them," Cesare whispers. Even his breath hot.

And then he is gone.

Micheletto looks to the other captains standing about the room and nods once, sharply.


It is no pleasure to drag Oliverotto shrieking and pleading from the room. Micheletto has clapped a hand over his mouth, but that helps little. His hands are fisted in Micheletto's shirtsleeves, struggling to free himself, and around them the other condottieri demand to know what is happening, why they are being treated thus, where Cesare is. Death should, when possible, be quick. And silent.

"His Excellency will see you when he is ready," Micheletto says as he hefts Oliverotto into the cellars. Once the four are there, it is the work of moments to bind their hands and feet, and prop them up against the walls. Micheletto is the last captain to leave, and he stands for a moment, framed in the light of the hallway, thinking how much easier it would be to have strangled these men where they sat. Death would be a mercy to them, but it pleases Cesare to delay it, so he must refrain.

He finds Cesare ahorse in the square, watching his troops move out into the streets. The square is crowded with men and wagons and horses, and Micheletto has to shove his way through to reach him. "It is not yet finished," Cesare tells him, staring north, toward the country they came out of. It is true enough. Vitelli's and Orsini's troops are camped a few miles away, in the castles and villas that once belonged to the ruling family of Sinigaglia. Cesare had taken all possible precautions, but it is likely that even now someone rides to them with word of what has happened here. And if there is not, they will see Cesare's men coming. Still.

"It is half finished, my lord."

The corners of Cesare's mouth twitch. "That is true enough. Come," he says then, turning his horse's head toward the river. "If I am to hold it, there must be no looting in this city."


"I must confess, your Excellency, when you said you could not forgive these men, this is not what I imagined you meant." Machiavelli, thin and sallow as death, leans through the cellar door to look at the four men. Cesare has ordered them tied back to back - Pagolo and Oliverotto; Vitellozzo and Gravina - it looks uncomfortable, Micheletto thinks, but not painful, which is a pity. "What will you do with them?

Cesare looks toward Micheletto, his gaze long and distant. "First I must receive word from the Holy Father that Cardinal Orsini has been arrested. Then… Well. God knows."

Machiavelli closes the door. "I must send word of this to Florence, you understand."

Cesare turns to look at him.

"But, I think," he says, "it will be difficult to find a messenger today. Perhaps tomorrow - or the next day, even. The streets are so dangerous right now."

"Perhaps you'll be able to find one on Friday."

"Friday. Yes, perhaps. The Signoria will be displeased to hear from me so late, but conditions being what they are, I don't know how they could expect anything sooner."

"Indeed." Cesare smiles. "Come, my friend," he says to Micheletto, turning away. "There is still work to be done. Machiavelli."

Machiavelli bows his head as they pass. "Il Valentino."


The tiny river to the north is not the Tiber, but it may have to do for disposing the bodies. They will march to Rome only when they are finished here. The citadel surrendered hours ago, but once Vitellozzo and the others are taken care of, there will be nothing to keep them. And since word has come from Rome of Cardinal Orsini's arrest, from a man on a lathered horse who asked seven ducats and received ten, it is time. Micheletto pushes open the cellar door.

Immediately, Oliverotto begins to plead for his life. "I meant you no harm, your Excellency," he tells Cesare. "You must believe me. Vitellozzo threatened me, said he would kill my sweet wife, my children, if I did not go along with the others. He said he would kill me, I didn't -"

"Lies," Vitellozzo snaps. "I said no such things."

"No, it's true! He came to my rooms in Cesena three months ago, put a knife to my throat, he thought of everything, he hired the men, it's because of Florence, my lord. He wants vengeance because they killed his brother, he thought of everything, please, it wasn't me -"

"Be quiet," Cesare says. His voice is sharp, but as he speaks it steadies, becomes almost gentle. This, Micheletto knows, is when Cesare is at his most dangerous, when he is steel cloaked in velvet. Once his voice would have shaken as he spoke. Once, he would have insisted on killing these men himself. But there is a different sort of satisfaction in watching a man die by your order, if not by your hand; Micheletto does not prefer it himself, but Cesare is learning to. "You betrayed me, you and Vitellozzo and the others. And you should know by now that I forgive nothing."

Cesare stands as still as Micheletto has ever seen him, his face as calm and still as stone. He is wearing his sword, and there is a knife at his left side, but he does not reach for either, or speak. Instead he glances at Micheletto, nods.

He always carries a garrote with him, and Micheletto reaches for it now. The thin metal is clean and sharp against his fingertips. Vitellozzo is demanding he be allowed to appeal to the Pope, and Oliverotto is not much better; as Micheletto slips the garrote over his neck the sweet, pungent smell of urine fills the room. No one acknowledges it. Micheletto, for his part, has seen worse.

"Please," Oliverotto whispers. "Please."

They will not die quietly. He can only do them two at a time, and as he grips the garrote around Oliverotto and Gravina the other two struggle and plead and cry for mercy. Cesare is smiling, just a little, and Micheletto allows himself to lean down, mouth close to Gravina's ear, and whisper: "I have never enjoyed killing men more. You should not have betrayed my master."

"I had my family killed in a room very much like this one," Gravina tells him, voice steadier than Micheletto would have expected. "It was dark. Stank of piss too, before the end. Better wall hangings, though." He's smiling. "Mm. But that was a day." Then Micheletto pulls the wire tight, as tight as he can, and Gravina Orsini dies like all men die by the garrote, writhing and kicking at the floor.


The first time he killed a man Cesare's eyes were wild even in the darkness; as he steps out of the room now, they are flat and hard. "They don't know how close they got," he says, turning to lean against the wall. "For a week I thought they might…." His body is a long sinuous line of exhaustion, but as Micheletto watches he pulls his shoulders in, lays his right hand on the hilt of his sword. "This will not happen again," he says, his voice harsh. "I swear it. In my own name, I swear it."

Micheletto turns toward the looters strung up in the square, toward the edge of the city and the sea beyond it, huge and uneasy in the dark. "Then it shall be so," he says.

This day was a great victory. Micheletto knows this already, knows that people will speak of it long after the two of them are dead. A great day - and a long day. He wishes for a bed, for the warm emptiness of sleep, but it is clear already that Cesare wishes to be gone. He has straightened from the wall, and is pulling his gloves from his pockets. Micheletto grips his doublet in one hand, firmly. He will not sleep tonight, he knows, not while they are on the road, where danger can come from any side. Cesare travels with a greater host than he used to, and is hated all the more for it. No, Micheletto will not sleep tonight. But sometimes Cesare speaks of his plans as they ride, and that passes the time.

Cesare reaches out, lays a hand on his shoulder. "Come," he says. "We must be on our way to Rome."


Further Notes: The best account of what happened that day can be found in Machiavelli's dispatches as ambassador to Florence. At the time, Machiavelli was attached to Cesare's court, and was an eyewitness to the aftermath, and heard Cesare's own account of what happened that day, which we assume was, for the most part, true. I've relied mostly on The Historical, Political, and Diplomatic Dispatches of Niccolo Machiavelli for the timeline presented in this story - but I have, in some things, taken liberties. The timeline is a bit compressed. Machiavelli never saw the condottieri himself, and actually sent two letters to the Signori of Florence that same day, the first of which is a very short note, the second of which has since been lost. Cesare may or may not have been present during the executions, which Micheletto certainly performed, but it would have been well in line with his character. Everything else is true.