The Wall Street Journal has a nice review of the old classic, including some good background history. Turns out I was wrong about his career. Not sure where I got the wrong information, but just goes to show that you can’t believe everything I say….
For even more detail, the New Yorker review of a biography of the man has pages and pages. Oddly, neither explicitly takes the position that I do: that Machiavelli is a classic Renaissance Man; His second career as a dramatist and historian pretty much seals that judgement.