I had the honor of co-teaching a seminar at Yale last week with my good friend Dr. Danilo Petranovich. The seminar, titled "Democracy, Statesmanship, and Greatness," focuses on leadership and the idea of greatness in democratic political systems.
My talk centered around the concept of political virtue in The Prince, and whether that concept was viable (or desirable) in the modern American context. I chose the "political question doctrine"--a legal concept holding that the federal courts should abstain from deciding certain cases over which it has jurisdiction under Article III of the U.S. Constitution--as a vehicle for these ideas. The federal courts have applied this doctrine to many cases involving the Presidential war-making powers and authority over other issues of foreign policy, and thus its scope defines in many respects the ability of the U.S. President to act as the Machiavellian Prince.
The topic seems ripe for additional research, and if anyone is interested, have a look at the handout I distributed to the class on the subject. (I took the liberty of correcting a typo in the first paragraph, however.) If you are a lawyer, you may find the discussion of the federal courts' Article III powers a bit over-simplified. Nuances could (and should) be added to any formal writing on the topic, but I deemed them distracting for a presentation of the topic to non-attorneys.