Chapter One

Niccolò Machiavelli was a young man of 17 years old when he was first introduced to La Volpe. The legendary thief had made quite an impression on him. He noted, with fascination, the strange color of the older man's eyes, and the way he rolled his r's when he spoke; he had never met a thief who possessed such diction until he met La Volpe.

Above all, it was La Volpe's cunning ways that won Machiavelli over; here was a man who could saunter through the sparsest plazas in Firenze—in broad daylight, no less—without so much as leaving a footprint on the ground. Huntsmen would search for him in vain, that is, until La Volpe sought them first.

On the other hand, La Volpe was not as thrilled when he made his first acquaintance with Machiavelli. He found his attitude better suited for someone much older and more accomplished than he was; it was almost repulsive to see this young person carrying his ambitions on his sleeve everywhere he went. There were also times when Machiavelli shrouded himself in secrecy and ambiguity, even with his fellow assassins.

Fortunately, the Assassin Order celebrated the diversity among its members. Through gentle coaxing from their leader, both assassins looked past their differences and managed to carry out their missions to completion—together. It was through continued collaborative work that La Volpe learned to trust his young accomplice and treated him with equal respect as the other assassins. He could clearly see that Machiavelli had wisdom beyond his years and that he was destined to become a leader one day. In return, Machiavelli regarded him as an exemplar assassin; he would silently observe and learn from his mysterious accomplice through the coming years.

But those days of mutual admiration were long gone.


Rome, 1500

The midday sun was unbearable.

He paused in his tracks to look up towards the distant hill that overlooked the ruins of the city. There was still a lot of ground to cover before he could reach his destination. If he had travelled by horse, rather than by foot, he would have been there already. Unfortunately, due to the Borgia's unrelenting grip over Rome's resources, horses had become a rare commodity. Machiavelli wondered if he should have waited until sunset before travelling to the Thieves' Guild—or why the thieves had to flock to the far reaches of the Antico District.

His arrival at the Thieves' Guild was met with the coldest of hospitalities: he noted some of the thieves huddled by the foot of the doorstep throwing him spiteful looks; others around him quietly scrutinized the Borgia-like colours he was wearing.

As a diplomat who has had considerable experience handling many unpleasant social affairs, it would take more than a few dirty looks to intimidate him.

One of the thieves broke away from the group to approach him; he looked about forty or so, sporting a scruffy beard, and a wool cap. Unlike the other members of his group, he was the least standoffish. Machiavelli wondered if he might have bumped into him before.

"How can I help you, Maestro Machiavelli?" the thief asked.

"I want to speak with La Volpe."

"You just missed him—he left this morning. "

"Where to?"

"He did not say."

Why must you make things difficult for me, La Volpe? Machiavelli thought. To say that his trip was a waste of his time is an understatement. He had written to him before and never received any replies—either in writing or in person. Why he refused any communications with him was beyond his comprehension. His uncooperative behaviour was infuriating and further degraded what was left of their Brotherhood—at least Bartolomeo justified his absence at the hideout.

Machiavelli let out a tensed sigh. "When he returns, will you tell him to meet me at Isola Tiberina? We have very important things to discuss."

The thief nodded and walked back from his post. Having spent his only purpose for visiting, he glanced one last time at the decaying building—the Thieves' Guild—before turning around to begin his trek back to Isola Tiberina. He was already making his way down the hill when a young woman sprinted from behind him holding a flask. She wore the same outfit as the other thieves but he did not recall seeing her anywhere near the Guild.

"Please take this with you," she said, offering the flask to him. "It is a long way back to your destination on foot."

"Grazie," he said, accepting the gift wholeheartedly. "To whom do I owe such kindness?"

"My name is Elena. I am one of La Volpe's thieves."

Machiavelli thanked her again before heading out. He had forgotten to fill his own flask with fresh water before leaving the area. It was strange that this person had seemingly come out of nowhere just to replenish his supply; but he decided not to question his piece of good fortune.

Besides, who in their right mind would decline water in this scorching heat?


After a long day of meetings with persons of various backgrounds—cardinals, guards, diplomats, mercenaries, thieves, courtesans, and the like—Machiavelli finally returned to the island that became his new residence in Rome. Tonight will be a quiet one, as it always had been these past few weeks. Despite his efforts to unite the Brotherhood once more, not one assassin was present when he arrived at the hideout—accomplishing nothing. As he sauntered through empty and cavernous hall of the hideout, he wallowed without concession in his own failure as a leader.

Thankfully, he was not entirely alone that night. The condottiero, Fabio Orsini, greeted him by the fireplace. The sight of him invigorated Machiavelli's spirits. After all, it was Fabio who had granted him full use of the storage facility (now the assassins' hideout) that once belonged to his family—the noble Orsinis.

"I did not expect you to be here, Fabio. What can I do for you?" Machiavelli said, easing himself down on an armchair to rest his weary legs.

The heavily armoured man chuckled. "Do not worry about me, amico mio. You have a lot on your plate already." He moved to sit across from Machiavelli. "I merely wanted to know how you were doing."

Machiavelli slumped on his chair slightly, the fingers on his right hand gently resting on the side of his face. "I'm managing," he replied, stone-faced.

The Assassin Order had not been the same since Cesare Borgia seized Monteriggioni and killed the Italian assassins' leader—Mario Auditore—just weeks ago. Through earlier arrangements, the newly-vacated leadership role fell onto Machiavelli without contest (perhaps because no one else volunteered?). As a man of action, he was keen on becoming the head of the Assassin Order; he could lay out the plans and have them implemented as he saw fit. But with little or no support from his principal allies—Bartolomeo d'Alviano, leader of the Roman mercenaries; La Volpe, leader of the Thieves' Guild; and Madonna Solari, owner of the Rosa in Fiore brothel—he quickly found that being a one-man army was too strenuous even for an ambitious man as himself.

Machiavelli, now 31 years old, preferred to work independently; but in times like these, he desperately needed Ezio's support. Even though he often clashed with him on many issues—such as Ezio's decision to spare Rodrigo Borgia's life—he knew that the Assassin Order would not have succeeded in their goals without Ezio Auditore's intervention. Ezio should be here, helping him piece together their fragmented Brotherhood—but where had he gone?

"It seems Cesare is wasting no time in capturing Romagna." Fabio said, leaning forward and resting his elbows on his knees. "He is already in talks with his generals to lead his army into the region." He clenched his jaw in anger. "Meanwhile, Roma sinks lower into poverty and decay."

The master assassin shook his head in displeasure. "I'm not surprised. His inexhaustible hunger for power drives him—he will not let anything hinder him from his conquests." A spark of hope lit up inside him. "At least we have the Apple."

The two men drifted into silence, until Machiavelli raised his head, as if he had just remembered something important.

"Any news about the Contessa? I wonder if she has returned to Forlì…"

Fabio disclosed that he has not heard anything about Caterina Sforza, the Countess of Forlì and Imola. He observed the look of concern on Machiavelli's tired face. Unable to provide any more useful information, he reverted to being just a caring friend to his ally: "You should get some sleep, Niccolò."

"You're right," Machiavelli muttered, standing from his chair, "I still have much to do tomorrow."

Sleep overcame him the moment he laid his fatigued body on his bed. His dreams were so vivid that night—he finds Ezio on a dirt road somewhere between Roma and Monterigionni, passed out next to his dead horse; Claudia takes charge of Rosa in Fiore; Bartolomeo screams bloody murder at the French General; and when he wakes up from his dream, he finds himself on La Volpe's bed, staring into those violet eyes.

Author Notes: The Italian words used in this chapter (indicated in italics) are standard in the AC universe. If they are unfamiliar to you, just google 'em. :)