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

Rulers and Reigns in Machiavelli's Europe

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Year Seq Place Person Comment
1422 0 France Charles VII  Charles VII was known as Charles the Well-Served (or the Victorious). He was well served by Jeanne d'Arc who inspired the victory that lifted the seige of Orléans and won the battle of 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 Succeeded Martin V, who was the first pope after the Great Schism of the Papacy (1378 - 1417).  
1434 0 Florence Cosimo  Cosimo takes power after ousting the old ruling oligarchi headed by the Albizzi family.  Cosimo parlayed his family's banking empire into political power becoming a political boss in Florence, a political system that Niccolò Machiavelli called a Cival Principality.
1435 0 Naples Alfonso I of Naples
1440 0 Empire Frederick III
1447 0 Papacy Nicholas V
1447 0 Milan Ambrosian Republic
1450 0 Milan Francesco I Sforza Francesco I Sforza  overthroughs the Ambrosian Republic in Milan. Recieved support from Cosimo de Mecici.  Marks major realignment of power coalitions among the big 5.  Was Florence and Venice vs. Milan and Naples.  Now Florence and Milan vs. Venice and Naples,  Pope is still the balancer.
1455 0 Papacy Calixtus III Formerly, Alfonso de Borgia, Calixus was the first Borgia pope.
1457 0 Papacy Pius II Enea Silvio Piccolomini
1458 0 Naples Ferdinand I of Naples  Also know as Ferdinand of Arogon, but not to be confused with Ferdinand the Catholic of Arogon, who was king of what was becoming Spain.
1461 0 France Louis XI (the Spider)
1464 0 Florence Piero (the Gouty) Piero succeeds to the position of first citizen on the death of Cosimo but lacks official status.  Members of Cosimo's ruling coalition challenge Piero, but Piero takes firm measures and consolidates power of the Medici regime.
1464 1 Papacy Paul II Formerly, Pietro Barbo
1466 0 Milan Galeazzo III Maria Sforza
1469 0 Florence Lorenzo (the Magnificant) Takes control easily and without challenge on Piero's death. However,  the Medici Bank declines.  Survives an assasscination attempt by members of the Pazzi family but emerges from the incident stronger and achieves near total control of the government.   Machiavelli born in Florance.
1471 0 Papacy Sixtus IV Formerly, Francesco della Rovere. Sixtus practiced nepotism on a grand scale and built the Sistine Chapel.
1476 0 Milan Gian Galeazzo II Sforza
1479 0 Spain Ferdinand V of Aragon (The Catholic) and Isabella of Castile. Aragon and Casstile united by death of  John II of Aragon and succession of son Ferdinand II of Aragon, who had already been married to Isabella of Castile.
1483 0 France Charles VIII (Father of his People)
1484 0 Papacy Innocent VIII
1486 0 Empire Maximilian I
1492 0 Florence Piero (the Fatuous) Piero, Lorenzo's  first son succeeded to his father's position as head of the regime.  Piero's diplomatic blunders durnig the first French invasion casused a revolution during which the Medici were driven out of Florence and the Bank collapsed.  
1492 1 Papacy Alexander VI Alexandar VI was Rodrigo Borgia, the father of Cesare Borgia.  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.
1494 0 Florence Republic Florence founds a republic modeled on that of Venice.  Piero Soiderini is named "Standard-bearer of Justice" for life, a position analogous to the Doge of Venice.   Machiavelli's career flourishes during this period.  The Republic remained an ally of France.
1494 1 Naples Alfonso II of Naples 
1494 2 Milan Ludovico Sforza
1495 0 Naples Ferdinand II of Naples
1496 0 Naples Frederick IV of Naples
1498 0 Milan Louis XII of France Machiavelli becomes Secretary to the Second Chancery of the Republic of Florence.
1500 0 Milan Ludovico Sforza 
1500 1 Milan Louis XII of France
1503 0 Papacy Pius III Pius, Francesco Todeschini Piccolomini, would have been more favorable to Cesare Borgia than was his successor.
1503 1 Papacy Pope Julius II Julius was Giuliano della Rovere, known as the warrior pope. He was a lifelong enemy of the Borgia.  Julius was Pope during the last year that Niccolò held office 1513
1504 0 Spain Joanna I (the mad) rules in Castile
1506 0 Naples Ferdinand III of Naples
1506 1 Spain Philip I (the hansome) rules in Castile
1512 0 Florence Giovanni (later Pope Leo X) Troops of the Spanish/Papal alliance ousted the French, defeated Florence, and restored the Medici regime in Florence.  The anti-French alliance installed Giovanni de Midici, Lorenz the Magnificant's second son and a Cardinal as head of the government in Florence.   Giovanni was Lorenzo The Magnificant's second son.  When Spain and Pope defeat the republic, the alliance install Medici to Florence.  Niccolò Machiavelli was thrown out of office and briefly imprisoned. 
1512 1 Milan Massimiliano Sforza Machiavelli driven from office.  Massimiliano is Lodovico Sforza's son.
1513 0 Papacy Leo X Leo, Giovanni de’ Medici, was the pope who held office when Niccolò wrote The Prince
1513 1 Florence Giuliano (Duke of Nemours) After Giovanni became Pope Leo X, he installed Giuliano as his puppet ruler in Florence. Machiavelli dedicates The Prince to Giuliano but after Giuliano's death changed the dedication to Lorenzo II (Duke of Urbino).
1513 2 Florence Lorenzo II  (Duke of Urbino) 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 Magnificant.
0 Milan Francis I of France
1515 1 France Francis I
1516 0 Naples Charles I
1516 1 Spain Joanna I (the mad) rules in Araton
1516 2 Spain Charles I (later to become Holy Roman Emperor)
1519 0 Papacy Giulio (later Pope Clement VII) On the death of Lorenzo II, Giovanni (Pope Leo X) appointed Giulio as puttet ruler of Florence. Giulio was the bastard son of Lorenzo the Magnificant's brother Giuliano, who was assicinated in the Pazzi conspiracy.
1519 1 Empire Charles V (Empire) = Charles I (Spain) Charles I of Spain is elected Holy Roman Emperor
1521 0 Milan Francesco II Sforza Son of Lodovico, and brother of Massimiliano
1522 0 Papacy Adrian VI
1523 0 Papacy Clement VII Giulio de’ Medici
1523 1 Florence Ippolito and Alessandro Ippolito (1511-1535) was the illigitemate son of Giuliano (Duke of Nemours).   Alessandro (1511-1537) was the illegetimate son of Lorenzo (Duke of Urbino).  Both Ippolito and Alessandro we also appointees of the Pope and together are often referred to as the Medici bastards.  
1524 0 Milan Francis I of France
1525 0 Milan Francesco II Sforza
1527 0 Milan Republic Sack of Rome - Niccolò Machiavelli died