Mercenaries

[Condottiere]

It's either one of history's most famous trolling documents, or a rather well sourced job application.

 

[Whipsnade]

While we are on the topic of The Prince, I detected a satirical tone to the work, where Machiavelli comes across to me as making subtle fun and jabs at the audience and their mores while overtly sucking up to them.

Well, he did write it while in exile.

I tend to agree with the assessment Condottiere mentions; it was a job application.

The fact that we catches hints of satire, jabs, puns, and other trolling fits the job application theory. During that period, being able to subtly "tease" or poke fun at your employer in such a way that they were amused while also admiring you intelligence and gall was considered a beneficial attribute.