I first read The Prince in high school, and I was tremendously disappointed. It's a small little thing and I was expecting the secrets of the ages. Or at least something that would help me deal with the cool kids who were making my life hell.
This time I decided to use my high school education to understand it better. No, not the mean-halls type of education, actual classroom instruction. That included a detailed history of Florence, where Machiavelli lived, because that was the city my high school was in.
No, I'm not Italian, although I speak it fluently. My parents moved there for work and sent us kids to the International School of Florence. Sounds nice, eh?
I hated it.
13 years later I've gotten over the hating and realized, damn, it WAS nice. I loved Florence, though I didn't love living there.
Machiavelli lived in Florence and grew to adulthood under Lorenzo Medici, who was a shrewed ruler of the city for many years until his death at a comparatively young age in 1492. Lorenzo Medici inherited the rule of Florence, after his father Piero and grandfather Cosimo. Before Cosimo, Florence had been a Republic. Lorenzo was 'Il Magnifico'. After he died, his son Piero was dubbed 'the Unfortunate' for messing everything up and getting the family temporarily kicked out of power.
Machiavelli served as part of the Free Republic of Florence, and when the Medici returned to power, he was tortured and exiled. He wrote The Prince and other political works during this period of exile, but it wasn't published until after his death.
The Prince refers to a surprising amount of chaos. Machiavelli is able to illustrate all of his theories with concrete contemporary examples of war, conquest, betrayal, and error. Italy didn't become a united country until the late 1800's. During Machiavelli's life, it was a boiling pot of different political parties and sovreignties. There was the Pope, who ruled large territories. There were the city-states. There were the neighboring rulers - France, Spain, etc. who had their eyes on plump prizes like Venice. And there was internal warfare as well. Florence tossed the Medici out, then they came back, then they got thrown out again, etc.
The Prince is more of a classification system than a how-to manual. Machiavelli divides the types of Princes into broad categories and outlines the best ways that each must use to hold on to his possessions. He seems to think that the way the Medici came to power was pretty good, because it's not easy for a foreign conqueror to get a Republic to give up its institutions. But of course, the Medici couldn't hold on to power during his lifetime. The book is dedicated to Lorenzo di Piero di Medici, son of Piero the Unfortunate, who is mostly remembered today for the magnificent tomb Michelango carved for him and for being the father of Caterina de Medici.
Why? Was he hoping to gain his favor, or was it some kind of ironic joke?
My theory (tentative and amateurish) is that the dedication is not ironic, and not an attempt at flattery, but made with an honest desire that the person in charge of Florence use his powers for the benefit of the people of Florence. Florentines are intensely loyal to their city.