Every time I read The Prince I become more convinced that it is
 a work of sarcasm.  Not conscious sarcasm perhaps, but sarcasm 
nonetheless. 
It is the product of bitter disappointment and 
disillusion.  This man, Machiavelli, had been a fierce Florentine 
patriot, a republican, a defender of the revolutionary city after the 
popular ousting of the plutocratic Medici psuedo-kings.  He lost the 
game and, having been tortured and exiled, he sat and wrote what is 
supposed to be a job application to the triumphant Medici... and it 
turns into the first open admission (in modern European letters) that 
ethics and politics are separate and often irreconcilable. 
It is coded,
 deliberately or not, to imply that the failure of Republican hopes in 
the face of the Medici stemmed from a failure to be sufficiently 
ruthless against them, to be as utterly cynical as the Medici 
themselves.  In the process, Machiavelli praises Cesare Borgia as the 
perfect Prince.  The Medici had regained their status in Florence partly
 owing to an alliance with the bellicose Pope Julius II, who had been one 
of the Borgia's most implacable enemies. 
Gramsci famously argued that 
the book was aimed at the common man, because the leaders to whom it was
 supposedly addressed already knew everything Machiavelli was saying.  
They just didn't talk about it.  In this reading, The Prince might become the whistleblowing of ruling-class 
secrets.  If you convert much of the advice into mordant irony, you find
 a book that laments a world in which people like the Medici can prosper
 precisely through a secretive, two-faced instrumentalism based on the 
most pessimistic view of mankind possible.  Of course, for the Prince 
himself, the most pessimistic view of mankind is actually the most 
optimistic, because it posits humanity as a weak and easily-exploited 
mass of flesh-puppets. 
The essentially double-edged nature of the rise of modernity (i.e. bourgeois social relations) is expressed in the book's implicit recognition of this.  Part of the promise of modernity, of its greater openness and ductility and possibility, is an inextricable co-habitee: opportunistic political tyranny based on the utilisation of people as counters, bargaining chips.  Money.  To be banked, exchanged, invested, harvested.  The market is the basis of Medici power.  They make society a market in which people are the tokens.
Machiavelli may have come to accept this view in the 
counter-revolutionary period after the fall of the Florentine Republic 
he championed, but I don't think his disillusion equates to an easy 
reconciliation with the kind of 'realpolitik' people often take from the
 book.  On the contrary, the book seems more like Michaelangelo's Last 
Judgement on the wall of the Sistine Chapel - a work of melancholy 
recognition of the failure of the liberatory promise of the renaissance,
 destined to be perpetually overlooked by the ceiling upon which the 
optimism is forever frozen.
 
 
 
Hi Sophie here, that's interesting stuff, I've read elsewhere that he was being sarcastic - TV Tropes I think. Incidentally in one of my favourite videogames Assassins Creed II you get to hang out with Machiavelli and do things for him. He's an interesting character.
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