Of the 3 men mentioned I believe Cesare Borgia would be the most successful in our modern world. Borgia was decisive, cruel, smart and ambitious which nowadays would not arguably be the most pleasant traits to live in society but they can get you places in the social order.
The choice of Borgia over Oliveratto and D’Orca comes from the fact that both of these men were somewhat successful in their own ways, however, in my opinion Cessare one ups them in many aspects. Oliveratto was a military commander and he only managed to hold his principality for 1 year until he lost it while D’Orca only commanded a principality in another’s name until his employer had him killed as a scapegoat.
The cruelty of Borgia is mentioned in the Prince,” cruel; notwithstanding, his cruelty reconciled the Romagna, unified it, and restored it to peace and loyalty” (Machiavelli) and although cruelty to us may seem unjust Machiavelli believed that the ability to be cruel was a key trait of a ruler. He uses Borgia as an example of how cruelty can be used to create success. His other traits are what most would consider necessities of a prince in order to control and secure his principalities from others.
As to what kind of profession Borgia would pursue nowadays I’d probably put him in some kind of organized crime as his cruelty would be commonplace among criminals and his political skills and decisiveness would eventually get him close to the top.
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