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Niccolò Machiavelli

“The Mastermind of Politics: Unveiling the Dark Secrets of Niccolò Machiavelli!”

Niccolò Machiavelli
Portrait of Niccolò Machiavelli by Santi di Tito
  • Alias: None
  • Gender: Male
  • Race: Human
  • Occupation: Philosopher, Writer, Diplomat
  • Religion: Roman Catholicism
  • Allies: Cesare Borgia, Lorenzo de’ Medici
  • Enemies: Pope Alexander VI, Catholic Church
  • Abode/Base of operations: Florence, Italy
  • Nationality: Italian
  • Languages: Italian, Latin
  • Alignment: Lawful Neutral
  • Affiliation(s): Republic of Florence, Medici family
  • Significant others: Marietta Corsini (wife)

Niccolò Machiavelli, a brilliant Renaissance thinker, is a man driven by ambition and the desire to understand the intricate workings of politics. With a sharp mind and keen observation, he dedicates himself to unraveling the complexities of power dynamics and human nature. Machiavelli’s purpose is to navigate the treacherous political landscape of his time and provide pragmatic advice to rulers, seeking to establish stability and secure their authority.

As a character, Machiavelli possesses a commanding presence, with piercing eyes that reflect both intelligence and cunning. He carries himself with a confident air, always attentive to the smallest details. In his pursuit of knowledge and influence, he immerses himself in the political realm, studying the rise and fall of leaders and analyzing the strategies employed by those who triumphed against all odds.

Machiavelli’s motivations stem from a deep understanding of the inherent complexities of human nature and the ever-shifting balance of power. He recognizes that political success often requires making difficult choices and employing methods that may seem ruthless to outsiders. Machiavelli believes that a ruler’s ultimate goal is the preservation and consolidation of power, as only a strong and stable leadership can ensure the prosperity and security of the state.

Driven by his unwavering dedication to uncovering the truth of politics, Machiavelli diligently records his observations and insights in his influential works, such as “The Prince” and “Discourses on Livy.” Through his writings, he aims to guide rulers, shedding light on the art of statecraft, diplomacy, and governance. Machiavelli’s ultimate aspiration is to shape the minds of future leaders, equipping them with the knowledge and wisdom to navigate the complex tapestry of politics and secure their place in history.

In his pursuit of political mastery, Niccolò Machiavelli faces adversaries who deem his methods unscrupulous and his ideas controversial. Nevertheless, he remains steadfast, fueled by a burning ambition to unravel the mysteries of power and leave a lasting impact on the world. Machiavelli’s enigmatic persona, coupled with his relentless pursuit of political wisdom, solidifies his reputation as a shrewd strategist and a formidable intellectual force in the annals of history.

Niccolò Machiavelli

Medium humanoid (human), lawful neutral

Armor Class 15 (studded leather) Hit Points 78 (12d8 + 24) Speed 30 ft.


Saving Throws Int +7, Wis +5 Skills History +7, Insight +5, Persuasion +4 Senses Passive Perception 12 Languages Common, Italian Challenge 6 (2,300 XP)

Actions Multiattack. Machiavelli makes two rapier attacks.

Rapier. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) piercing damage.

Political Influence (Recharge 5-6). Machiavelli uses his persuasive skills to influence a target within 30 feet. The target must succeed on a DC 15 Wisdom saving throw or become charmed by Machiavelli for 1 minute. While charmed, the target is friendly to Machiavelli and will follow his suggestions as long as they don’t directly contradict the target’s nature or beliefs. The target can repeat the saving throw at the end of each of its turns, ending the effect on a success.

Reactions Master Strategist. When a creature within 30 feet of Machiavelli misses him with an attack, he can use his reaction to impose disadvantage on the attack roll.

Legendary Actions Niccolò Machiavelli can take 2 legendary actions, choosing from the options below. Only one legendary action option can be used at a time, and only at the end of another creature’s turn. Machiavelli regains spent legendary actions at the start of his turn.

Rapid Maneuver. Niccolò Machiavelli moves up to his speed without provoking opportunity attacks.

Words of Influence. Machiavelli speaks a few choice words to a creature within 30 feet. The creature must succeed on a DC 15 Wisdom saving throw or be charmed by Machiavelli until the end of its next turn.

Strategic Insight (Costs 2 Actions). Machiavelli imparts tactical knowledge to an ally within 30 feet. The ally gains advantage on its next attack roll or ability check.

Equipment Rapier, studded leather armor, quill and ink, leather-bound notebook, pouch with 25 gold coins.

Magic Items Amulet of Persuasion. While wearing this amulet, Machiavelli has advantage on Charisma (Persuasion) checks. Ring of Mind Shielding. Machiavelli can wear this ring to protect his thoughts from being read or detected.

Tactics and Personality Niccolò Machiavelli is a cunning and calculating political strategist, always seeking the most advantageous position for himself and his allies. He uses his wit, charm, and knowledge of political maneuvering to sway others to his cause. Machiavelli prefers to avoid direct combat whenever possible, relying on his diplomatic skills to achieve his objectives.

In battle, Niccolò Machiavelli focuses on disabling his enemies through his rapier attacks while using his Political Influence ability to charm and manipulate key targets. He strategically positions himself on the battlefield, analyzing the situation and providing tactical insights to his allies.

Machiavelli’s surroundings are often filled with books, maps, and scrolls, reflecting his scholarly and analytical nature. He is typically calm and composed, his mind always calculating the best course of action. Machiavelli’s mood is one of calculated determination, driven by his desire to secure and maintain power in the realm.

Plot Hooks

  • The Shadow Advisor: The players receive a cryptic message directing them to a secluded location where they meet a cloaked figure known only as “The Shadow Advisor.” This mysterious individual offers his services as a strategist and political advisor, claiming to possess intimate knowledge of the players’ enemies and the inner workings of the realm. Machiavelli reveals his goal to manipulate events from the shadows, ensuring that the players achieve their objectives while subtly advancing his own agenda. As the players work alongside Machiavelli, they begin to question his true motives and wonder if they are mere pawns in his grand scheme.
  • The Manipulated Noble: A powerful noble seeks the aid of the players to eliminate their political rivals and consolidate their power. Machiavelli approaches the players, secretly orchestrating the noble’s actions through calculated manipulation. As the players carry out their tasks, they become entangled in a web of deception, political schemes, and Machiavellian tactics. They must decide whether to become accomplices in Machiavelli’s machinations or find a way to outmaneuver him and free themselves from his grasp.
  • The Controversial Treaty: The players are chosen to act as mediators in a critical treaty negotiation between two warring factions. Sensing an opportunity to shape the political landscape, Machiavelli offers his services as a consultant, guaranteeing his strategies will secure a favorable outcome. However, his approach involves compromising the interests of one faction to achieve overall stability. The players must navigate the treacherous waters of diplomacy, balancing loyalty, ethics, and the long-term consequences of their decisions while under the watchful eye of Machiavelli.
  • The Lost Manuscript: In their travels, the players stumble upon an ancient and forbidden manuscript attributed to Niccolò Machiavelli. The manuscript contains hidden knowledge, political strategies, and Machiavelli’s insights into power dynamics. Its contents draw the attention of powerful individuals and secret societies who will stop at nothing to possess it. The players find themselves caught in a race against time, pursued by relentless enemies, and forced to decide the fate of the manuscript: to protect its dangerous secrets or use them to further their own ambitions.
  • The Machiavellian Heist: Machiavelli approaches the players with a proposition—a daring heist to retrieve a legendary artifact from an impenetrable fortress. The success of the mission relies on Machiavelli’s meticulous planning and the players’ execution of his carefully crafted strategies. However, the heist involves sacrifices and morally ambiguous choices, blurring the line between right and wrong. The players must decide if they are willing to embrace the Machiavellian mindset and tread the treacherous path of deception and manipulation.
  • The Political Chessboard: The players find themselves thrust into a complex political landscape where various factions vie for dominance. Machiavelli, recognizing their potential, offers his guidance to navigate the intricate web of alliances, betrayals, and power struggles. As the players become entangled in a high-stakes game of political chess, they must grapple with the ethics of Machiavellian tactics and decide whether to employ them or forge their own path to success, all while Machiavelli watches with a keen eye, evaluating their every move.

Currently in the World

Niccolò Machiavelli is a middle-aged man with a stout build and a well-groomed beard. He has a prominent forehead, deep-set eyes, and a sharp gaze that reflects his intelligence and keen observation. His dark hair, streaked with gray, is neatly combed and falls just below his shoulders. Niccolò carries himself with an air of confidence and authority, always dressed in formal attire befitting his position.

Currently, Niccolò is sitting at his study desk, surrounded by books, scrolls, and writing materials. The room is adorned with maps, political diagrams, and portraits of influential figures. The shelves are filled with volumes of ancient texts and manuscripts, showcasing his extensive knowledge. The faint scent of ink lingers in the air, a testament to his continuous writing and research.

His mood is contemplative, as he ponders the complex web of political dynamics and power struggles. Niccolò’s face shows a mix of determination and curiosity, eager to uncover the secrets of successful leadership. He scribbles notes on parchment, formulating strategies and analyzing historical events. Though the task at hand is demanding, his passion for political theory and governance fuels his drive to unravel the intricacies of power.

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