The Annotated Prince - The Prince by Niccolò Machiavelli with notes by Gene Gessert

Timeline Machiavelli’s Italy

Here is a table that shows a timeline for the key events in Machiavelli’s life and in the power struggles in Renaissance Italy that shaped his understanding of politics. The entry for each event tells when and where and what happened. The description (what) contains a headline and a comment, which explains the significance of the event in Machiavelli’s work.

When Where What
1417-0 Papacy

Martin V elected Pope, ending the Papal Schism

Martin, formerly Otto Colonna, was elected pope by the Council of Constance, which necessarily claimed authority superior to that of the Pope.  Martin's election ended the Papal Schism 1378 to 1417.  The schism had grown out of the Avignon Papacy 1309 to 1378 when the Papacy was located in Avignon, and dominated by France.  The Avignon Papacy ended in the Schism, a period of contested succession, during which there were rival popes in Rome and in Avignon.  After his election, Martin returned the Papacy to Rome in 1420.  Both the Schism and the Avignon Papacy weakened the Church in two respects: (1) In church affairs, the Pope had lost influence relative to Councils and the Cardinals; (2) In secular affairs, the Church lost control of the Papal States.  Its quest to recover effective control of the Papal States, especially the Romagna and the Campagna, forms an important, continuing political current in Machiavelli's Italy.

1422-0 France

Charles VII becomes king of France

Charles VII was known as Charles the Well-Served (or the Victorious).  In particular, he was well served by Jeanne d'Arc who inspired the victory that lifted the siege of Orléans and won the Battle of Patay (1429), which allowed Charles to be crowned at Rimes.  Patay was the turning point of the 100 Years war, which concluded in 1453 with the Battle of Castillon at which Charles forces under Jean Bureau defeated John Talbot.

1431-0 Papacy

Eugenius IV elected Pope

Eugenius, formerly Gabriele Condulmer, succeeded Martin V, the first pope after the Great Schism.  Eugenius faced insurrection in Rome (supported by the Colona family), which caused him to flee the city, and encroachment on his authority from the Council of Basel.  He was, after 10 years, able to return to Rome and he successfully asserted Papal supremacy over the conciliar movement.  He was not, however, able to establish order in Rome, which would remain threatened by rival families, like the Colona, which were known collectively as the Barons of the Campagna (the rural area around Rome).

1434 0 Florence

Cosimo de' Medici becomes de facto ruler of Florence

Cosimo took power after ousting the old ruling oligarchy headed by the Albizzi family.  Cosimo parlayed his family's banking empire into political power becoming a "party boss" in Florence, thus building a state that Niccolò Machiavelli called a Civil Principality.

1440 0 Empire

Frederick III elected King of the Germans

King of the Germans was the traditional designation for someone who had been elected but not yet formally crowned as Emperor. Later, (1452) Frederick of the house of Hapsburg was crowned by the Pope in Rome.  He was the first Hapsburg to rule the Empire.

1442-0 Naples

Alfonso I seizes Naples

Alfonso was King of Aragon and in 1442 took Naples from the rival claimant, Rene of Anjou.

1447-0 Papacy

Nicholas V elected Pope

Formerly Tommaso Parentucelli, Nicholas consolidated papal power and began rebuilding Rome. It was Nicholas that crowned Frederick III as Holy Roman Emperor

1447-1 Milan

Ambrosian Republic founded in Milan

On the death of the last of the Visconti dukes of Milan ( Filippo Maria Visconti) a popular movement founded a republic, which was named in honor of St. Ambrose.

1450-1 Milan

Francesco I Sforza seizes Milan

Condottiero, Francesco I Sforza, overthrew the Ambrosian Republic in Milan, with financial support from Cosimo de Medici.  This marked a major realignment of power coalitions among the "Big 5" Italian city states.  Formerly the configuration was Florence and Venice vs. Milan and Naples.  It now became Florence and Milan vs. Venice and Naples, with the Pope as the balancer.

Sforza is Machiavelli’s case study of a prince that gains power by his own skill and experience.

1453-0 Byzantium

Mehmed II conquers Constantinople

Mehmed II was Sultan of the Ottoman Empire.  He followed one of Machiavelli's guidelines for holding power when he moved his court to the city, and thus improved his chances of securing the new territory.

1455-0 Papacy

Calixtus III elected Pope

Formerly, Alfonso de Borgia, Calixtus was the first Borgia pope.

1455-1 Empire

Gutenberg prints the Bible

The Gutenberg Bible was the first book that Guttenberg published with the newly invented method of printing with movable type.  Printed books would make it much more difficult for the Papacy to suppress the Lutheran heresy than it was for it to suppress earlier reform movements, which had to rely for propaganda on the circulation of copied manuscripts.  

1457-0 Papacy

Pius II elected Pope

Formerly Enea Silvio Piccolomini, Pius struggled against the Roman Barons in the Campagna and to subdue his vassal Sigismondo Pandolfo Malatesta, Lord of Rimini in the Romagna.  His efforts were not decisive or lasting in either area.

1458-0 Naples

Ferrante succeeds Alfonso as King of Naples

Ferdinand I (usually called Ferrante so as not to confuse him with Ferdinand the Catholic of Aragon, Isabella's husband) was the bastard son of Alfonso I).  This Ferdinand was an ally of Pope Sixtus in the war that followed the Pazzi Conspiracy.  That war was intended to punish Lorenzo the Magnificent de' Medici for retaliating against those churchmen who had tried to assassinate him.  However, Lorenzo traveled to Naples in person, and was able to make a separate peace with Ferdinand.

1461-0 France

Louis XI succeeds Charles VII as King of France

Known as the Spider, Louis signed the Treaty of Picquigny formally ending the Hundred Years War with England.  Louis began the consolidation of France by annexing Burgundy and Picardy.   By Machiavelli's day this consolidation would reach the stage where France was able to intervene in Italy. 

1464-0 Florence

Piero (the Gouty) succeeds Cosimo in Florence

Piero succeeded to the position of first citizen on the death of Cosimo but lacked official constitutional status.  Hence, members of Cosimo's ruling coalition (led by Luca Piti) challenge Piero by mounting an attack known as the Pitti Conspiracy. However, Piero took firm measures and thus consolidated the power of the Medici regime.

1464-1 Papacy

Paul II elected Pope

Formerly Pietro Barbo, Paul advanced the pope's struggle with the college of cardinals for dominance of the papacy by packing the college with his own supporters.  He also curtailed papal patronage for humanists, which he considered to be promoting paganism.

1466-0 Milan

Galeazzo Maria Sforza succeeds Francesco in  Milan

Galeazzo succeeded his father as Duke of Milan without incident.   However, in Florence, Francesco's passing called into question Milan’s continued alliance with Florence, which provided critical military support to the Medici regime.  Uncertainty about Galeazzo’s commitment to the Florence-Milan alliance emboldened a cabal of anti-Medici oligarchs (the Pitti Conspiracy) to attempt to overthrow Piero, but in the event, Galeazzo’s sent Piero 3,000 troops and the rebellion collapsed.

Soon Galeazzo would become hated by important figures in his own court who later assassinated him in church. Machiavelli would counsel princes to avoid hatred, especially among those who have ready access to them at court.

1469-0 Florence

Lorenzo (the Magnificent) de' Medici succeeds Piero in Florence

Lorenzo took control easily and without challenge on Piero's death. However, the Medici Bank declined. On 26 May 1478, in a replay of the Visconti assassination, members of the Pazzi family and other conspirators, attacked Lorenzo in church.  The attack killed his younger brother (Giuliano), but failed to kill Lorenzo, who emerged richer and stronger than he had been before the incident. He would later achieve near total control of the government and would dominate the city in which Machiavelli grew up.

1469-1 Florence

Machiavelli born in Florence

Machiavelli was born in Florence, the banking center of Europe and the epicenter of the Renaissance.

1469-2 Spain

Ferdinand of Aragon marries Isabella of Castile

Ferdinand and Isabella, later known as the Catholic Monarchs, were second cousins, both being descended from John of Castile of the House of Trastámara.  Spanish Cardinal Rodrigo Borgia (the future Pope Alexander VI) facilitated the union procuring a dispensation from Pope Pius II, which allowed the two to marry. Potentially their union represented a close alliance of the two most powerful families and regions in central Spain.   Although Isabella ruled Castile, her husband formally became King Ferdinand V of Castile "by right of his wife."

1471-0 Papacy

Sixtus IV elected Pope

Formerly, Francesco della Rovere, Sixtus is notable for: appointing his nephew, Giuliano della Rovere (the future Warrior Pope Julius II) as cardinal, collaborating in the assassination of Lorenzo the Magnificent, and annulling the decrees of the Council of Constance, and building the Sistine Chapel.  Annulling the council's decrees advanced the Pope's power position relative to the consular movement and the Cardinals.  Building the Sistine Chapel introduced the Renaissance to Rome.

1473-0 Papacy

Pope grants Girolamo Riario Imola

Pope Sixtus IV gave his nephew Girolamo the city state of Imola as part of the arrangements for his marriage to Caterina Sforza, the daughter of the Duke of Milan, Galeazzo Maria Sforza.  Caterina would survive her husband as ruler of Imola and Forli.  Machiavelli's first diplomatic mission would be to her court.

1474-0 Spain

Isabella becomes Queen of Castile

Half of the potential of Spanish unification was realized when Ferdinand's wife, Isabella became Queen on the death of her brother Henry IV of Castile.

1476-0 Milan

Gian Galeazzo Sforza succeeds Galeazzo Maria in Milan

On the assassination of his father, Galeazzo Maria Sforza, Gian Galeazzo (age 7) inherited the Duchy of Milan with his uncle Ludovico (Il Moro) Sforza acting as regent and de facto ruler.  In 1488, Gian Galeazzo Sforza married Isabella of Aragon, the daughter of King Alfonso II of Naples.  Alfonso's interest in Milan would later stimulate conflict between the two regions and would break up the alliance of Milan, Florence, and Naples.  

1477-0 France

Charles (the Bold) Duke of Burgundy dies

At this time, the Duchy of Burgundy included lands that today are in France and the Low Countries. Since Charles had no male heirs and according to French Law, his daughter Mary could not inherit, Charles' lands reverted to the crown (in the person of Louis XI, the Spider).  However, Mary would shortly wed Philip the Handsome, the son of Maximillian I, who was the son and heir of Emperor Frederick III.  After political and military maneuvering, the Treaty of Senlis (1493) resolved the conflict.  France retained the Duchy's French territories and the Empire would rule the Netherlands. The French Burgundian lands would further strengthen royal power relative to that of the French Nobles. France, was on its way to becoming sufficiently powerful to contemplate intervention in Italy.

1477-1 Empire

Maximilian weds Mary of Burgundy

Mary was the daughter of Charles the Bold, Duke of Burgundy. The two were wed in August 1477, 7 months after the death of her father. After Mary's death in 1482, the Low Countries passed to Philip the Handsome, and would eventually pass to Philip's son, who would be the Emperor Charles V.

1479-0 Spain

Ferdinand succeeds John II as King of Aragon

The full political potential of the marriage of Ferdinand and Isabella was finally realized on the death of his father, John II of Aragon.  Ferdinand, who was already King of Sicily (since 1468), now became Ferdinand II of Aragon known as Ferdinand the Catholic and history would call the couple "The Catholic Monarchs." Their reign would alter Europe's power hierarchy.  They would drive the Moslem powers from Spain and use the Spanish Inquisition like a secret police force to suppress potentially dissident Moslems and Jews.  After 1492, their financing of the discovery and development of the Americas would bring Spain enormous wealth.  The marriage of their daughter, Joanna (the mad), with Philip (the handsome), the son of the Holy Roman Emperor Maximillian would unite the two families into the leading power in Europe, a competitor to the Valois kings of France and the main counter force opposing the Ottoman Turks.  

1481-0 France

Charles IV, Duke of Anjou dies

With the death of Charles VI of Anjou without male heir, the County of Province and the Duchy of Anjou became possessions of Louis XI and the French crown.  Assimilation of Province (with its ports of Toulon and Marseille) made France a Mediterranean power.  From the house of Anjou, Louis also inherited the family's claim to Naples, which his son Charles XII would later assert by invading Italy.

1483-0 France

Charles VIII succeeds Louis XI as King of France

Having inherited both the claim and the means to intervene in Italy, Charles soon announced that he intended to press his claim to Naples.  In 1491, Charles further consolidated royal power relative to the Hapsburg Emperors by marrying Ann of Brittany, who had in the previous year already been married by proxy to the future Emperor Maximillian I.  The stage was now set for foreign intervention in Italy, which would be the central political challenge of Machiavelli's political career. 

1483-1 Empire

Maximilian I rules with Frederick III

Maximillian ruled jointly with his father Frederick III, who was the King of the Germans and Holy Roman Emperor.

1484-0 Papacy

Innocent VIII elected Pope

Innocent (formerly Giovanni Battista Cibo) would later be noted for his role in the first French invasion of Italy. In 1489, Innocent excommunicated King Ferdinand I of Naples and invited Charles VIII to assert his claim to Naples.  Charles needed no encouragement, but from the standpoint of the other Italian powers, this wasan unfortunate diplomatic signal.

1486-0 Empire

Maximilian I named heir apparent

At the instigation of his father, Frederick III, Maximillian was elected King of the Romans, the traditional title of the heir apparent of the Empire.

1492-0 Florence

Piero succeeds Lorenzo 

Piero (the Fatuous), Lorenzo's first son, succeeded to his father's position as head of the regime.  In 1494 Piero's diplomatic blunders during the first French invasion would cause a revolution during which the Medici were driven out of Florence and the Bank collapsed.  

1492-1 Papacy

Alexander VI elected Pope

Alexander VI was Rodrigo Borgia, the father of Cesare Borgia.  Alexander would use the power of the papacy to help Cesare conquer the Romagna and incidentally, make Cesare a powerful prince in his own right. Cesare is Machiavelli's leading example of a Prince who founds an entirely new state from scratch, but does so, not by his own power, but by the means of a more powerful ruler, in this case his father, the Pope.

1492-2 Spain

Catholic Monarchs conquer Granada

Ferdinand and Isabella, known together as the Catholic Monarchs, made their triumphal entry into Granada, marking the end of the Reconquista, the re-conquest of Moslem held Spain.  Not only did the re-conquest enhance the power and augment the unification of Spain, but its battles forged a new army.  The army, often under the leadership of General Gonzalo de Córdoba, was based on a core, not of heavy cavalry, but on artillery and infantry.  In the course of the Italian Wars, armies would increasingly adopt the Spanish model, relying less on Men at Arms, and more on infantry and artillery.   Also in this year, the Monarchs financed Columbus discovery of the Americas, whose revenues would eventually help finance their expansionism.  Thus, like France, Spain had grown capable of intervention in Italy.

1493-0 Empire

Frederick III dead, son Maximillian I takes reins

On the death of his father, Maximillian, who was already named King of the Romans, became Holy Roman Emperor, though he was never formally crowned by the Pope.  He would remain Emperor during the entire time that Machiavelli was in the Florentine government. 

1493-1 Florence

Savonarola predicts invasion

Savonarola predicted that God would send a great king from the north on a divine mission to cleanse the Church of its corruption.  He had gained popularity and influence owing to his fiery sermons and reputation for prophesy.  For a time, he would become the most influential figure in Florence.  However, in chapter VI of The Prince, Machiavelli would call him an "unarmed prophet," because his power was based only on popular support.  

1494-0 Italy

Charles VIII invades Italy

Charles VIII launched the first French invasion of Italy to press his claim to Naples.  His forces easily crushed the feeble Italian resistance.  However, holding power proved more difficult than seizing power, and his invasion would have little effect on Italy, except in Florence, where it would bring down the Medici regime.  In addition, since Savonarola viewed Charles' invasion as a mission from God, he pushed Florence to become and remain a French ally. This would put Florence at odds with other Italian states, which would unite to oppose France.

1494-1 Florence

Piero de' Medici cedes Pisa to French

Piero (the Fatuous) cedes Pisa and 3 fortresses (which controlled the Arno River) to the invading army of Charles VIII of France.  Charles would never returned Pisa.

1494-2 Florence

Medici regime collapses

The oligarchs and populous of Florence outraged by Piero's concessions to France, violently evicted the family from the city.

1494-3 Florence

Florentines proclaim a Republic

After the fall of the Medici, Florence founded a republic modeled on that of Venice, but with a broader (though still meager) popular participation.  Girolamo Savonarola, whose own power was based solely on popular support promoted populist features in the new government.  After Savonarola's demise, Machiavelli would serve in the new regime and his patron, Piero Soderini, would later be named "Standard-bearer of Justice" for life, a position roughly analogous to the Doge of Venice.  

1494-4 Naples

Alfonso II succeeds Ferrante

When Ferrante died, Alfonso was leading his father's forces opposing Charles VIII's invasion of Italy to seize Naples.  He ruled, as Alfonso II for less than a year until Charles' advance induced him to abdicate in favor of his son, Ferdinand, usually called Ferrandino.

1494-5 Milan

Ludovico Sforza succeeds Gian Galeazzo II 

After the suspicious death of Gian Galeazzo II Sforza, Ludovico Il Moro, who had been the state's de facto ruler, became Duke in his own right

1495-0 Papacy

Charles VIII driven out of Italy

In response to the frighteningly easy French victory in Italy, Pope Alexander VI formed the League of Venice to drive Charles out of the peninsula.  Under Savonarola's influence, Florence refused to join the League and remained a French ally.

1495-1 Naples

Ferrandino succeeds Ferranti

After his father's abdication Ferrandino ruled as Ferdinand II of Naples.  With the advance of Charles VIII, Ferrandino fled to Messina in Sicily which was ruled by Ferdinand the Catholic of Aragon.  Under the auspices of the League of Venice coalition (formed by the Borgia pope, Alexander VI), Ferrandino was able to obtained the aid of Ferdinand the Catholic's general Gonzalo de Córdoba, and with him was able to drive the French troops from Naples.

1496-0 Naples

Frederick IV succeeds Ferrandino

On Ferrandino's premature death, Naples fell to his uncle Fredrick, who ruled as Frederick IV.

1496-1 Spain

Joanna the Mad marries Philip the Handsome

Joanna was the daughter of the Catholic Monarchs (Ferdinand and Isabella), and heir presumptive of Castile and Aragon.  Philip was Duke of Burgundy (his mother was Mary of Burgundy).  Philip's father was Maximillian I, the Hapsburg Emperor.  Their son would become Charles V, who would rule as his inheritance: the Holy Roman Empire, the Hapsburg domains in Austria, Burgundy, most of Spain, and the Spanish lands in the Americas.

1497-0 Florence

Savonarola excommunicated

Pope Alexandra VII, angered by Savonarola's support for France against his League of Venice, excommunicated the Dominican friar.

1498-0 Florence

Savonarola executed

Owing to his excommunication and public relations missteps, Savonarola lost popular support.  Now able to appease the Pope without incurring popular hostility, the government of Florence tried and executed Savonarola.  

1498-1 Florence

Machiavelli named to Chancery

In June, the governing council of the Republic of Florence (the Signoria) elected Machiavelli Secretary to the Second Chancery, which managed internal affairs.  In July he became secretary to the Ten of War, which was responsible for defense related diplomatic issues. In 1507, he would be assigned to the Nine of the Militia, which raised a troops that were used in the war to recover Pisa. 

1498-2 Florence

Florence attacks Pisa

To recover the city, Paolo Vitelli (in the employ of Florence) launched his first campaign against Pisa.  Supporting Vitelli, Florence hired Ottaviano Riario (son of Caterina Sforza of Imola and Forlì) as a precaution against an attack from Venice.  Imola and Forlì controlled the approach to Tuscany from Venice and the North East and connected Florence to the commerce of the Adriatic. Machiavelli negotiated the Riario's contract with Caterina. Despite precautions, however, Venice was able to attack Tuscany.

1498-3 France

Louis XII succeeds Charles VIII

With the death of Charles VIII, a branch of Valois kings ended.  That branch had comprised: Charles V, Charles VI, Charles VII, Louis XI (the Spider), and Charles VIII. Hence the line of inheritance reverted back to the last branch in the family tree, to Charles V's other son and Charles VI's brother, Louis I the duke of Orléans.  That branch comprised Louis I of Orleans, Charles of Orleans, and Louis II of Orleans who would rule as Louis XII of France.  Hence, Louis XII's succession united two powerful branches of the Valois and further consolidated power in France.

1499-0 Milan

Louis XII seizes Milan

Louis invaded Italy to press his claim to both Milan and Naples. Louis quickly overthrew Ludovico Sforza (who escaped to the court of Maximillian I) and then moved South. Machiavelli considered his attack on Milan sound policy, but considered his initiative in Naples to be strategic overreach and mistaken in its approach since he was obliged to form an alliance with a powerful potential competitor, Ferdinand the Catholic of Aragon.  

1499-1 Romagna

Cesare Borgia takes Forli and Imola

Cesare Borgia (son of Pope Alexander VI) began his conquest of the Romagna with the financial and diplomatic support of the Pope and with troops from the invading army of Louis XII.  For the troops, Alexander had negotiated a bargain with Louis. According to its terms, Cesare gained: (A) the Duchy of Valence, (B) Marriage with Charlotte d'Albert, the sister of the King of Navarre, and (C) French troops for his conquest of the Romagna. With Valance, Cesare acquired the title by which Niccolò often referred to him, Duke Valentino. From the bargain, Louis gained (A) his divorce (B) a Cardinal's hat for a favorite counselor, George d'Amboise, (C) Cesare's assistance in Louis's planned invasion of Milan. The Borgia's aim was to: (A) reassert papal control of the Romagna, (B) drive out the numerous warlord princes who dominated key areas, and (C) unite the region under Cesare's personal control and rule it as a Papal fief.

1499-2 Florence

Florence and Venice sign pact

Venice and Florence reached an agreement whereby Venice withdrew its troops from Tuscany, setting the stage for another Florentine attack on Pisa. 

1499-3 Florence

Florence renews attack on Pisa

Paolo Vitelli launched his second campaign for Florence against Pisa. Vitelli stormed the Stampace tower, near the Porta a Mare.  His troops pressed the attack but Vitelli turned them back.  On 15 Sep, the Ten of War wrote begging Vitelli to press the attack.  Machiavelli probably wrote this letter on behalf of the commissioners, who privately suspected Vitelli of taking bribes from Pisa.  Vitelli resumed the expensive bombardment of Pisa, but failed to take the city. Florentine commissioners then abducted Paolo Vitelli, who was taken to Florence and beheaded on the roof of the Palazzo della Signoria.  

This experience probably did much to form the dim view of mercenary troops that Machiavelli expressed in Chapter 12 of The Prince.

1500-0 Milan

Ludovico Sforza retakes Milan

Sforza staged a brief comeback, which was enabled by support from Maximilian I and popular disillusionment with the French.  This was one of many incidents that supports Machiavelli's observation that people frequently support outsiders to improve their position, only to find that they have gone from bad to worse.

1500-1 France

Machiavelli on mission to French court

The Signoria sent Machiavelli on a diplomatic mission (regarding Pisa) to Louis and Cardinal George d'Amboise of Rouen.

1500-2 Milan

Louis XII retakes Milan

After Sforza's return to power his mercenary army disintegrated. Louis' forces then decisively defeated Sforza who was captured and imprisoned in France for the duration of his life. Machiavelli observed that the rebellion and its suppression provided Louis with a pretext for additional harsh measures that made Louis' grip on Milan firmer than it had been prior to the uprising.

1500-3 Romagna

Cesare Borgia continues conquests

In the second phase of his campaign, Cesare conquered Pesaro and Rimini in the Romagna.

1501-0 Naples

Louis XII seizes Naples

Under pressure from French troops and without support from the Ferdinand Catholic of Aragon, Frederick IV resigned as King of Naples and retired to France. Ordinarily, Ferdinand might have been expected to defend his kinsman, Frederick, but as noted above, Louis partitioned southern Italy with Ferdinand. This avoided war with Aragon in southern Italy, but Machiavelli considered the attack on Naples overreach. He argued that if Louis could not conquer by himself, bringing in Ferdinand, even to avoid war, was a blunder.

1501-1 Romagna

Cesare Borgia campaigns in Romagna 

In his third campaign, Cesare continued his attacks along the Via Emilia with conquests of Faenza and Brisighella. He then intimidated Florence, marched across Tuscany and besieged Piombino, which soon fell.  

1502-0 Romagna

Cesare Borgia begins fourth campaign

Cesare continued operations in Tuscany, threatening Florentine interests in the Val di Chiana, an area which runs from Arezzo and Siena (in Tuscany) to Perugia and Terni in Umbria. One of Cesare's mercenary captains, Vitellozzo Vitelli (brother of Paolo who the Florentines had beheaded) conquered Arezzo, but Florence's ally, Louis, would eventually force Cesare to order Vitellozzo to return the city to Florentine control.  Finally, Cesare, by treachery and the swiftness of his attack, conquered Urbino. The Signoria sent Machiavelli to meet with Cesare. The two met for the first time in Urbino from which Machiavelli reported his favorable impression of the new prince.

1502-1 Romagna

Anti-Borgia confederacy formed at Magione

Cesar's successes, particularly that at Urbino, triggered a conspiracy among his mercenary captains, who feared his expanding power.  In October 1502, Cesare's captains met at Magione with Giovanni Bentivoglio (lord of Bologna), Guidobaldo da Montefeltro (formerly of Urbino), and Pandolfo Petrucci (lord of Siena) to plot a revolt against Cesare. Several members of the Orsini family also joined the Magione conspiracy.  These included Cardinal Orsini, Paolo Orsini, and Francesco Orsini, Duke of Garvina.  They attacked Urbino and defended Bologna against Cesare's attack there.  During this period, the Signoria sent Machiavelli as envoy to Cesare at Imola, where he remained for 3 months.

1502-2 Romagna

Ramiro de Lorca killed in sensational execution 

Ramiro (aka Ramiro de Orco) was Cesare Borgia's severe, much hated, but effective governor in the Romagna.  To shift blame and conciliate public opinion, Cesare had him cut in half and left as an exhibit in the public square at Cesena. Machiavelli remarked that "the barbarity of this spectacle caused the people to be at once satisfied and dismayed."

1502-3 Romagna

Borgia murders Magione conspirators at Senigallia 

Though he had made peace with them, Cesare no longer relied on the conspirators, who had formerly been his chief mercenary captains. With financial help from Alexander, he engaged new mercenaries and prepared to continue his campaign with an assault on Senigallia to which on 31 December 1502, he summoned the conspirators. There he trapped them and except for Gianpaolo Baglione who refused the summons, Cesare arrested his former captains.  He executed Oliverotto Euffreducci and Vitellozzo Vitelli during the night, but sought permission from Pope Alexander before executing Paolo Orsini, a relative of a prominent cardinal. 

1503-0 Papacy

Alexander VI and Cesare gravely ill

Pope Alexander and his son Cesare Borgia both caught malaria in Rome.  Alexander died on 18 August.  Cesare recovered, but too slowly to cease and hold control of his new lands in the Romagna.  Without the financial support of the Pope, Cesare's nascent empire unraveled. 

1503-1 Papacy

Pius III elected Pope

Pius, Francesco Todeschini Piccolomini, would have been more favorable to Cesare Borgia than was his successor, but he lived for only a few months.

1503-2 Papacy

Pope Julius II elected Pope

Pius III was succeeded by Julius (Giuliano della Rovere) known as the warrior pope. By the time of Alexander VI's death in August 1503, Cesare Borgia had regained direct control of the Romagna for the Papacy by expelling the so-called Vicars of the Romagna.  The Vicars had nominally ruled their territories as fiefs of the Pope, but in fact ruled in their own right.  Although he was a lifelong enemy of the Borgia keeping control of the former territories of the Vicars would continue to be Julius' main preoccupation.  However, as Cesare's power collapsed, Venice began, with help from the dispossessed Vicars, to seized control of some of his Romagna territories, setting up a conflict that would touch off the League of Cambri Wars.

1503-3 Rome

Machiavelli in Rome

When Pope Alexander VI died, Machiavelli was on a diplomatic mission in Rome and observed Cesare's downfall at first hand.

1504-0 France

Machiavelli in France

In this year, Machiavelli undertook his second diplomatic mission to France.

1504-1 Spain

Joanna the Mad succeeds Isabella

In spite of her mental instability, Joanna (the Mad) inherited the crown of Castile from her mother, Isabella.

1504-2 Naples

Ferdinand the Catholic seizes Naples from Louis XII

Ferdinand (the Catholic) of Aragon drove out Louis XII's forces and ruled the kingdom himself as Ferdinand III of Naples. 

1505-0 Papacy

Pope nearly trapped in Perugia

In a campaign to attempt to recover some of his lands from the Vicars and Venice, the Pope impetuously entered Perugia in advance of his troops.  Unaccountably, Giovanpagolo Baglioni, lord of that city, failed to attack the Pope and his Cardinals, when he could have killed them all before the Papal troops arrived.  Machiavelli remarked on this incident in The Prince, Chapter 25.

1506-0 Spain

Philip I (the Handsome) King of Castile

Philip secured the crown on the grounds that Joanna was insane. 

1506-1 Spain

Philip I (the Handsome) Dead

Philip died probably of Typhoid and again Joanna was, in principle, Queen of Castile, and tried to rule in her own right.

1506-2 Rome

Machiavelli in Rome

Machiavelli returned to Rome on a diplomatic mission to Pope Julius.

1507-0 Spain

Ferdinand rules Castile - Joanna declared insane

Joanna (the Mad: Juana la Loca) remained the titular Queen of Castile, but was confined to a Nunnery.  Ferdinand ruled for her as regent.

1507-1 Empire

Machiavelli in Germany

The Signori sent Machiavelli on a diplomatic mission to Emperor Maximilian. In Chapter 10 of The Prince Machiavelli would report a favorable impression of the German free cities.

1508-0 Papacy

Pope Julius II forms League against Venice

Julius formed the League of Cambri to strike back at Venice for its encroachment in the Romagna. The League comprised Julius II, Louis XII, Emperor Maximilian I, and Ferdinand I the Catholic.

1509-0 Papacy

French defeat Venice

Under the banner of the League of Cambri French troops defeated Venice at the Battle of Agnadello.  In the aftermath, Venice quickly lost all its lands on the mainland.

1510-0 Papacy

League of Cambri dissolves

Venice made peace with Pope Julius II, who then sought to drive France out of Italy.  To oppose France, Julius employed Swiss mercenaries, but also invited Venice to help as an ally.

1511-0 Papacy

Pope Julius proclaims League against France

The Holy League comprised Julius II, Henry VIII of England, Emperor Maximilian I, Venice, and Ferdinand I the Catholic (the dominant military force).

1512-0 Papacy

French win key battle

In April of 1512, the Battle of Ravenna pitted the French commander Gaston de Foix against Ferdinand the Catholic's general Ramón de Cardona, acting for the Holy League.  De Foix was the victor, but he was killed in the battle.

1512-1 Papacy

French driven from Milan

In August of 1512 Swiss and Venetian troops fighting for the Holy League drove French forces from Milan.

1512-2 Milan

Massimiliano Sforza installed in Milan

After the French defeat, the Holy League installed Maximillian Sforza as puppet ruler. Massimiliano was Ludovico Sforza's son.

1512-3 Florence

Giovanni de Medici rules in Florence

In August Pope Julius II induced Ferdinand the Catholic's general Ramón de Cardona to attack Florence, to punish it for having refused to join the Holy League.  League troops defeated Florence, and restored the Medici with Giovanni (Lorenzo the Magnificent's second son, a Cardinal and the future Pope Leo X) as head of the government.  

1513-0 France

France and Venice form alliance

Owing to dissention in the Holy League over the allocation of territory, Venice left the League and allied with France to oppose Julius II, Emperor Maximilian I, and Ferdinand I the Catholic.  The alliance was formalized in the Treaty of Blois.

1513-1 France

French defeated in Milan

In May 1513, at the Battle of Novara, a French army tried to oust Maximillian Sforza from Milan.  They were soundly defeated by Swiss troops and this initiated a series of French defeats.  This left Venice to face the Spanish alone, but their contest remained a stalemate.

1513-2 Papacy

Leo X elected Pope

Leo, formerly Giovanni de' Medici succeeded Julius I.  Leo (the pope who held office when Niccolò wrote The Prince) was much less militant than Julius and Papal initiatives in the Romagna ebbed.

1513-3 Florence

Machiavelli fired

Niccolò Machiavelli was thrown out of office and briefly imprisoned, as the new Medici regime took power.

1513-4 Florence

Giuliano (Duke of Nemours)  installed in Florence

After Giovanni became Pope Leo X, he installed Giuliano as his puppet ruler in Florence. Machiavelli originally dedicated The Prince to Giuliano but after Giuliano's death changed the dedication to Lorenzo II (Duke of Urbino).

1513-5 Florence

Machiavelli writes The Prince

Machiavelli wrote The Prince and started work on The Discourses. 

1513-6 Florence

Lorenzo II  (Duke of Urbino) installed in Florence

After Giuliano's sudden death, Leo X installed Lorenzo as his puppet ruler in Florence.  Lorenzo II was the son of Piero the Fatuous and the Grandson of Lorenzo the Magnificent.

1515-1 France

Francis I succeeds Louis XII

When Louis XII died without a male heir, yet another branch of the Valois ended.  That branch (the Orléans Dukes) comprised Louis I of Orléans, Charles of Orléans, and Louis II of Orléans who ruled as Louis XII of France. Hence the line of inheritance reverted back up the family tree to Louis I of Orléans and Charles of Orléans brother, John Count of Angoulême.  Charles son, would rule France as Francis I.  This line would include the Sun King, Louis XIV, and would rule France until the death of Henry III in 1589. In July 1515, Francis invaded Italy to recover Milan, and defeated Swiss forces at the Battle of Marignano. After the defeat and with the Leo X's less warlike disposition, Francis and Leo reached a peace settlement, signaling the end of the Holy League.

1516-0 Spain

Ferdinand dies - Joanna rules 

Again, notwithstanding her insanity, on the death of Ferdinand II of Aragon and under the terms of his will, Joanna (the Mad) inherited Aragon.

1516-1 Naples

Charles  succeeds Ferdinand in Naples

Immediately on the death of his grandfather, Ferdinand the Catholic, Charles (future Emperor Charles V, but now still resident in the Netherlands, succeeded to his father's title as Charles II of Naples. 

1516-2 Naples

Frances and Charles sign accord on Naples

In August 1516, Francis I and Charles II reached an agreement (Treaty of Noyon) whereby France held Milan and Spain held Naples. 

1517-0 Spain

Charles "co-ruler" with Joanna

Charles (the future Emperor Charles V), son of Philip the Handsome and Joanna the Mad, arrived in Castile to assert his right to rule in Castile and Aragon, but he was 18, not yet 20, when he could legally rule in his own right. However, he was able to effectively rule Castile (with his mother nominally as co-regent). 

1517-1 Florence

Machiavelli completes The Discourses. 

The Discourses is a commentary on the first ten books of Livy, which cover the period when ancient Rome was a republic. 

1517-1 Empire

Martin Luther posts 95 theses

In a reaction against the sale of indulgences in Wittenberg, Martin Luther posted 95 theses (statements for disputation), which asserted that indulgences and other practices of the Church were theologically unsound.  The incident is a milestone in the Protestant Reformation which would break the religious monopoly of the Papacy and lead to religious wars in the Empire.

1518-0 Florence

Machiavelli writes The Mandrake Root

The Mandrake Root was a satirical comedy, which is still in print and still amusing.

1519-0 Florence

Giulio de Medici installed in Florence

On the death of Lorenzo II, Giovanni (Pope Leo X) appointed Giulio as puppet ruler of Florence. Giulio was the bastard son of Lorenzo the Magnificent's brother Giuliano, who was assassinated in the Pazzi conspiracy.

1519-1 Empire

Charles elected Emperor Charles V

Charles II's election as Emperor Charles V represents the peak of Hapsburg power.  Although he could not unify or integrate his empire, he did formally unite: The Low Countries, the Spanish crowns of Castile and Aragon, Spanish possessions in the Americas, the Hapsburg domains, and the Holy Roman Empire.  Thus although Charles' empire gave him access to vast resources, those resources could not be an optimally effective instrument of policy, because his empire lacked organization and he lacked an effective means of unified control. Nonetheless, Charles election altered the power relationships in Europe, because Charles's dominions now surrounded France.

1521-0 France

Francis I attacks Navarre and the Low Countries

Charles II of Spain's election to the crown of the Holy Roman Empire as Charles V, upset the tenuous balance of power embodied in the Treaty of Noyon, and reignited the power struggle between Francis I and Charles. In 1521 Francis I attacked Navarre and the Low Countries, prompting Charles V to form an alliance with Henry VIII and Pope Leo X, who made common cause with Charles to combat the spread of the Lutheran heresy in the Empire. 

1521-1 Milan

Charles V takes Milan

In a counter move to French attacks, Charles V invaded Milan and installed Francesco II Sforza (the second son of Ludovico (il Moro) Sforza and brother of Massimiliano) as a puppet ruler, but nominally Duke of Milan.

1522-0 Milan

French driven from Lombardy

Charles's forces, aided by Francesco II Sforza, defeated the French at the Battle of Bicocca and drove them from Lombardy.  

1522-1 Papacy

Adrian VI elected Pope

Adrian (also his name before election) was Dutch, from Utrecht.  Before election he was tutor to Charles V and and then Inquisitor General of Castile and Aragon. 

1523-0 Papacy

Clement VII elected Pope

Clement, formerly Giulio de' Medici was the bastard son of Giuliano de' Medici, the assassinated brother of Lorenzo the Magnificent. Pope Leo X (formerly Giovanni de' Medici) had made Giulio a cardinal. Clement would be Pope during the Sack of Rome.

1523-1 Florence

Ippolito de' Medici rules Florence for Giulio de' Medici

Ippolito (1511-1535) was the illegitimate son of Giuliano (Duke of Nemours).  When Giulio de' Medici was elected Clement VII, Ippolito ruled Florence as his agent.

1525-0 Milan

French counter attack in Milan fails

Francis I made another attempt to invade Milan, but was defeated at the Battle of Pavia. Francis was captured and imprisoned in Spain.

1526-0 Spain

Francis I and Charles V peace deal

While in Spanish captivity, Francis I signed a peace agreement, Treaty of Madrid, by which he forfeited his claims to Italy, Flanders, and Burgundy.  After his release, Francis renounced the Treaty and formed the League of Cognac to oppose Charles V.  The League's members included Pope Clement VII, Venice, Henry VIII, Francesco II Sforza of Milan, and Florence.

1527-0 Rome

Charles V's troops sack Rome

Emperor's troops sack Rome.   The Sack of Rome occurred in the same year as Machiavelli's death, and is a milestone in the decline of the Italian Renaissance.  The sack was an unplanned aftereffect of an engagement between Emperor Charles V and the League of Cognac, an alliance of Francis I and Pope Clement VII.  Charles V's troops were primarily mercenaries.  They defeated Francis I's troops, but after the battle, Charles lacked the funds to pay them.  To recoup their expenses, the mercenary leaders determined to march to Rome, attack, and plunder the city.  The troops attacked the city in May of 1527.  The expedition's nominal leader, Charles Duke of Bourbon was killed in the initial attack, leaving the troops with no effective control.  The city was so severely destroyed that for a time it ceased to function as a major Italian city. 

1527-1 Florence

Republic in Florence

During the Sack of Rome, Pope Clement VII (Giulio de' Medici) was gravely threatened and took refuge in the Papal fortress, Castel Sant'Angelo. The predicament of the Medici Pope emboldened leading families in Florence to revolt and set up a short lived republic. However, after making peace with Emperor Charles V, Clement restored the Medici to power in Florence, ending the last republic. 

1527-2 Florence

Niccolò Machiavelli dies

On 21 June 1527 Machiavelli died, remembered at the time, if at all, as a former minor official of the old Republic.  Today, Machiavelli's place in the intellectual history of western civilization dwarfs that of nearly all of his contemporaries.