What is the political situation that prompted Machiavelli to write The Prince?

In 1511, Machiavelli was a Florentine diplomat, respected and secure in his position. He was an agent of Piero Soderini, often sent abroad to represent Florence, and highly esteemed as both a scholar and a political mind. Then came 1512, and the fall of the Florentine Republic. Despite Machiavelli’s objections, the Florentine government relied heavily on its French allies; when the French jumped ship, Florence was left to face the papacy, brimming with strength due to its alliance with Spain. The Spanish infantry crushed the Florentine armies, and the government collapsed. The Medicis, a powerful family who had earlier ruled the city, returned. Machiavelli was implicated in a conspiracy and thrown in prison, where he was tortured and threatened with execution for a period of time. Then tempers changed, and he was released as an exile. He retreated to the country, and there wrote The Prince.

The book is prefaced as a plea to the Medicis; it is offered as a gift to Lorenzo. It did not wind up having the desired effect, and Machiavelli never again regained the position in politics he had earlier enjoyed. The book itself was not published until after his death, in 1532. Since then, however, it has grown exponentially in stature, and is today regarded as one of the most important political treatises ever written.