(Aug 11) Election of Rodrigo Borgia as Pope. Takes the name of Alexander VI. This begins an eleven-year era of Borgia control in Rome and central Italy which will determine every diplomatic move of the Republic of Florence.

(Nov 9) Piero de’ Medici (son of Lorenzo) tries to arrange an agreement with King Charles, but when he returns to Florence the city turns on the Medici family. Piero and his brother Giovanni (the future Pope Leo X) are forced to flee the city in the middle of the night. The mutual agreement between the Medici family and the Republic of Florence is over and in the future, Medici control in Florence will be reasserted only at the head of a foreign army.

(Nov 17) King Charles VIII of France enters Florence with thousands of troops. The conquered city is forced to host the army in its palaces. One wit said, “Charles conquered Florence with a piece of chalk,” referring to the quartermaster’s chalk that marked the handsome Florentine palazzi that would be taken over by the French troops. Niccoló Machiavelli, now twenty-five years old, watches consumed with shame as the thousands of French troops march into his city and pass his house.

(Feb) King Charles enters Naples. As of February, he has been able to move all the way down the peninsula with almost no opposition. Italy looks weak and disunited. Now a new alliance called the Holy League (that name will be used again so be careful when you see it: The Holy League Holy League of 1495) forms between the Pope, Milan, Venice and Spain to drive the French out of Italy.

(July 6) Battle of Fornovo near Modena. The vast forces of almost all of Italy engage the French army at Fornovo in an attempt to destroy the power of King Charles VIII. The leader of the Italian forces is Francesco Gonzaga from Mantua, husband of Isabella d’Este. The Italians fail to unite their forces (a kind of symbol of their behavior during the whole previous year) and the French successfully withdraw north to fight another day. The lesson for Machiavelli is: Italian disunity aids the enemy.

(Mar 18) Savonarola preaches his last sermon.

(Apr 7) Followers of Savonarola undergo trial by fire as a test of the truth of his preaching. Opinion in Florence turning rapidly against him.

(Apr 7) On the same day as the ordeal in Florence, the King of France dies unexpectedly Charles VIII is gone from the scene and is succeeded by his cousin Louis XII. Louis even more interested in Italy than Charles had been.

(May 22) Savonarola Executed along with two of his followers in the Piazza Signoria by hanging and then the corpses are burnt and the ashes are strewn over the waters of the Arno. This public execution of a political leader is a rare event in Florentine history and remains a frightening reminder of crowd psychology and mass hysteria. Observers like Machiavelli find the whole episode embarrassing for Florence.

(June 16) Machiavelli appointed to the government of the Signoria (the governing council of Florence) as head of the Second Chancery and also as secretary to The Ten of War, the Florentine office that controlled Florentine military matters. Machiavelli is sent immediately as ambassador to the government of Caterina Sforza in the small city of Forlí and Imola. These were very important cities for Florence since they formed a northern barrier along the Apennines for the Florence territory. The Borgias and especially Cesare were looking at Forlí as a potential state for the stateless Borgia children.

Cesare Borgia beginning to build a papal state along the coast and the Apennines north of Florence. This is dangerous for Florence and soon Machiavelli will be sent to deal with Cesare.

(Nov 11) Treaty of Granada, a secret treaty, signed between Louis XII and King Ferdinand of Spain in which the two monarchs agree to divide Italy between them. Spain will get the south (Sicily and Naples) France will get the north. After a few more battles, the two monarchs settle into their two spheres of influence.

(Feb) Machiavelli travels to nearby Pistoia to assess Florence’s allies to the northwest.

Machiavelli goes to Siena as Florentine ambassador to government of Pandolfo Petrucci as the threat of Cesare Borgia grows in central Italy.

Machiavelli’s good friend Piero Soderini is appointed to this position. It is Soderini who protects Machiavelli in his government job right to the end of the Soderini regime (1512).

(June) Cesare Borgia completes a lightning quick invasion and conquest of the strategic city-state of Urbino. All Italy is shocked. Urbino was supposed to be an ally of the pope. Now it seemed that no friend of Pope Alexander VI was safe. Anything and anyone would be sacrificed (maybe even Florence!) in order to build a state for his son Cesare.

(June) Machiavelli arrives in Urbino to meet Cesare for the first time. This is one of the great encounters in history since it is during his days with Cesare that Machiavelli forms many of the ideas he will write down ten years later in his book The Prince. One can understand why Machiavelli was impressed with this ruthless twenty-seven year old prince of the Borgia family. Here was Cesare, so recently a nobody, now ruler of a growing state bordering Florentine territories. The roads were filling with the petty tyrants of small states, now wandering homeless and lamenting the unprincipled actions of this papal son. Machiavelli met Cesare in the spectacular rooms of the ducal palace of Urbino. Machiavelli now saw Cesare up close: tall, handsome, brilliant, with his shoulder-length coal black hair giving him the aura of some superhuman ancient Greek hero.

(Dec) The Massacre at Sinigaglia. Cesare Borgia lures a group of petty tyrants to a peace meeting at Sinigaglia and then has them all strangled. So much for peace!

(Oct) Florence sends Machiavelli to Rome to meet with the new pope. These recent events add to the material Machiavelli is collecting for his book on government. The totally unexpected events of the last months now provide more material for Machiavelli’s book on government. Cesare Borgia’s fall had been as rapid his ascent.

Machiavelli begins plans for his citizen militia. This is one of his most cherished ideas of governmental reform: that the Republic should rely not on paid mercenaries but instead on its own well-trained citizens in a citizen militia. He writes his ideas in a book On the Art of War.

Pope Julius II established the League of Cambrai with Spain, France and the Holy Roman Empire ( Maximilian in Germany) against Venice. Venice defeated by this alliance at the Battle of Agnadello the next year. Now that he has tamed Venice, the pope will turn on France.

(August) The allies meet at The Congress of Mantua and decide the fate of all regimes in Italy. Giovanni de’ Medici gets the pope’s agreement to the return of the Medici to Florence with Spanish troops leading the family back to power. These 6,000 troops move south through the Apennines to the south side where they rested at Prato, a Florentine ally. The commander asks Florentine cooperation in a peaceful return of the Medici to Florence. Piero Soderini leads the democratic forces in a rejection. The troops at Prato go out of control of their commanders and run wild sacking the whole city of Prato. More than 4,000 people are slaughtered. The minute that Florentines can reach their city to report the sack, Florence resistance to the return of the Medici collapses, and Piero Soderini is thrown out of power. He sneaks out of the city under protection of darkness exactly the way the Medici had done eighteen years before.

(August 31) The Medici Return to Florence. The republic is at an end. Now Medici functionaries will rule the city for an absent Medici pope in Rome for the next fifteen years.

(Nov 7) Niccoló Machiavelli is fired from his post as Secretary. He is now out of his government job and never gets back in. The Medici see him as an intimate of Piero Soderini and therefore not to be trusted.

(Feb 21) Death of Pope Julius II in Rome.

(March 11) Election of Giovanni de’ Medici as Pope Leo X. Now the Medici will rule from Rome, reaching back to their home base in Florence and controlling every move of the Florentine government. This new Medici rule in Florence is totally different than the one operated by Lorenzo de’ Medici. Now the Medici are back in Florence with the help of foreign troops. There is a great deal of dissension and anti-Medici feeling on the part of republican circles and within those circles Machiavelli is one of the most prominent leaders.

(March 13) Machiavelli is freed from prison and exiled to his country house in Sant’ Andrea in Persussina in the hills south of Florence. Here is where he spends most of the rest of his life (to 1527). Much of his time he uses writing.

(Dec 10) Machiavelli writes to his friend Francesco Vettori that he has completed a book on government called The Prince.

(Sept 13) Battle of Marignano. The French, led by a vigorous, young King Francis I, return to Italy and reconquer northern Italy at this battle. French defeat a coalition of papal and imperial troops. Now once again, Italy will be the scene of an international duel between the aggressive new king of France and the vigorous new king of Spain. For the next ten years, Italy will be torn apart as these two battle for control of the whole of the Mediterranean.

(Dec 17) Concordat of Bologna. Pope Leo X meets King Francis I of France and signs a concord between the papacy and France that addresses payment of fees to Rome and other issues. The papacy will now be caught up in this duel between France and Spain as both attempt to coerce the pope into supporting their claims to Italy and other holdings. Both Pope Leo X and his successor Pope Clement VII attempt to walk a tightrope between the two powers.

(March 18) Pope Leo’s brother Giuliano de’ Medici (called the Duke of Nemours) dies unexpectedly in Fiesole thus complicating all the Medici plans for a rule in central Italy.

(June) With Giuliano dead, Pope Leo turns to his nephew
Lorenzo de’ Medici, the son of his brother Piero who had lost the Medici rule in the debacle of 1494, and now gives Lorenzo papal troops to take Urbino for a new larger Medici state. (Thus the Medici pope repeats exactly the action of his Borgia predecessor who had handed Urbino to his son Cesare). This Lorenzo de’ Medici is the person to whom Machiavelli dedicates his book The Prince in an attempt to win the favor of the Medici. This change of loyalties by the old republican has received severe censure by later historians who find it embarrassing that Machiavelli seemed willing to do anything to return to government. But by 1516 it was clear that Florence would remain in the hands of the Medici and Machiavelli concluded that he had no other choice.

In Casatico near Mantua, Baldassare Castiglione completes his
The Book of the Courtier based on conversations held at Urbino.

(June 28)
Election of Charles V, King of Spain as Holy Roman Emperor. This is one of the most important political events of the early 16th century. Charles had a strong claim to the imperial throne as a direct descendent of the recently deceased Maximilian, his grandfather. Therefore, when the Electors met, they were besieged by Spanish bribes of unbelievable proportions fueled by American gold, and by counterclaims by every other ruler in Europe determined to stop this joining of Spanish power to the imperial power. The anti-Charles forces failed and on June 28 he became both Holy Roman Emperor (Germany) and continued as King of Spain. He will hold this duel power until the 1550’s when he tires and abdicates in favor of his son and brother. This election has important repercussions for Italy. It means that the balance of power among those states fighting for predominance in Italy has suddenly shifted in favor of this new Spanish-Imperial power and any smart Italian leader should have understood that France was finished in Italy and that the future in the peninsula would be heavily influenced by this new international government in Madrid.

Pope Clement VII is now caught. International forces are all converging upon him both in military and diplomatic forms. King Henry VIII of England is demanding a divorce. The King of Spain is warning the pope not to do it: Catherine of Aragon is his beloved aunt.

Pope Clement VII, dabbles with a French alliance as he faces the terrible truth that Spanish-Imperial power has him boxed in. King Charles of Spain sends his forces south.

Poor Machiavelli, who more than anyone else, had warned of this exact danger, lived just long enough to hear the terrible tales of the Sack of Rome. He died on June 22, 1527, at Sant’Andrea in Percussina.