1494- The Medici expelled from Florence. Machiavelli Appointed clerk to Adriani in the second chancery.
1498- Adriani becomes chancellor and Machiavelli succeeds him as second chancellor and secretary.
1499- Sent to Forli to negotiate the continuance of a loan to Catherine Sforza.
1500- Sent to France where he meets with Louis XII and the Cardinal of Rouen.
1502- Marries Marietta Corsini. Sent to Romagna as envoy to Cesare Borgia where he witnessed the events leading up to Borgia's murder. Machiavelli's political philosophy was highly influenced by his study of Cesare Borgia.
1503- January, returns to Florence.
1504- Second mission to France.
1506- December, submits a plan to reorganize the military to Pierre Soderini, Florence's gonfalonier, and it is accepted.
1508- Sent to Bolzano to the court of the Emperer Maximilian.
1510- Sent once more to France.
1512- The Medici returns with a Spanish army and Florence throws out Soderini and welcomes the Medici. Machiavelli dismissed from office and retires to San Casciano.
1513- Imprisoned after accused of participation in a conspiracy. Is tortured and then released upon Giovanni de Medici's election to the papacy. Returns to San Casciano and writes The Prince.
1515- Writes La Mandragola.
1519- Consulted by the Medici on a new constitution for Florence which he offers in his Discourses.
1520- Appearance of The Art of War and The Life of Castruccio Castracane. Commissioned to write the History of Florence.
1526- Clement VII employes Machiavelli first in inspecting the fortifications of Florence and then sending him to attend the historian Francesco Guicciardini. He meets Guicciardini in Bologna later in the year as well.
1527- June 20, dies in Florence.