The Prince
Niccoló Machiavelli appears in canon (although he sadly does not have enough appearances yet to be appable) as a student at the same university Cesare is attending (and he did actually go there during those years, although probably not in the role the manga gives him, haha) and was sent as a diplomat to Cesare's military campaigns in the early 1500's. Cesare had a great influence on the development of his thoughts on political theory and science and he praised him in The Prince, the text for which he is now (in)famous. Machiavelli is shown to be already watching him with interest in canon and Cesare already displays signs of becoming that brilliant if idealized leader.
The chapter that focused the most on Cesare (although he and his father are both brought up several times throughout the entirety of the text) is Chapter VII: Concerning New Principalities Which Are Acquired Either By The Arms Of Others Or By Good Fortune. Cesare's career was seen to be a good example of this, since he started with the aid of King Louis XII of France who gave him (as part of the diplomatic maneuvering which also included a cardinal's hat for the king's advisor and a royal marriage for Cesare) a body of troops to command as he wished, provided he first aid him in his ventures in northern Italy. Cesare also became a ruler through fortune because it was his father's machinations that enabled him to attempt to create a state out of the Romagna in the first place. Machiavelli saw this as an opportunity handed to him not by dint of his abilities (although he also thought that Cesare was perhaps the most qualified man for the job) but because of the chance of his birth.
The difficulty, then, since Cesare became a prince through the arms of others and through good fortune, was making it so that he was not forced to rely on either of these things to hold on to his state. Machiavelli complimented Cesare's movement towards self-reliance by replacing Louis' men with his own and disarming or removing those "allies" who were waiting for the opportunity to take his gains for themselves, so that "when all the actions of the duke are recalled, I do not know how to blame him".
Machiavelli believed, however, that Cesare ultimately failed in his goal to create a state for himself since he was unable to hold on to it after Alexander VI's death. But unlike the other men he uses as examples, he cannot quite bring himself to put down on paper a simple formula describing where he went wrong and how another in his position could have succeeded. Instead he vacillates, changing his mind throughout the chapter on why Cesare was unable to maintain his grip on the Romagna. Machiavelli worked closely with Cesare for some time and greatly admired him even when Cesare's forces were threatening his beloved Florence. The Prince is written after Cesare's loss of power and after Machiavelli met with him in the depths of his despair and some of the tension in his writings reflects this fall of an idol (I should note that I'm not taking the text as satire--at least not the portions that deal with Cesare's specifically. This is because it does line up very neatly with what he had previously written about him in diplomatic dispatches that, presumably, were not meant to be satirical.). However, enough time has passed that the portrait Machiavelli paints in his text is not as bitter and disappointed as his letter to the Florentine government that depicted Cesare as a mad and broken man is, even if it is also not as (perhaps naïvely) exuberant and awed as his original impression was. There is still clearly a great deal of admiration being expressed, and Machiavelli eventually is forced to come to the still somewhat wistful conclusion that ultimately it was fortune that was responsible for Cesare's fall.
In canon, Cesare is not mature enough yet to really epitomize this prince, but he does certainly know promise. It is stated several times that he is very good at winning over people (this is much harder to accomplish in Camp where every third or fourth person has heard of the Borgia legacy) and he is clearly capable of moving behind the scenes. He already knows what he wants (although his idea of how to accomplish it differs somewhat from what eventually happens) and he is determined to achieve it. Cesare is aware that there are certain things he needs from people but he maneuvers the best he can so that he is not in a position where he is forced to rely upon them. Rather, they should be giving them to him as favors or to pay debts. The only people he truly leans upon are family and those who are intimate enough to be considered family, something that can be seen in his later life as well. Cesare understands that, at least at this point in his life, it is through the whim of his birth that he has the opportunities he does. At the same time, however, he is determined to do all he can to capitalize on this chance. If Fortune is a boat, he is already at the helm.
The chapter that focused the most on Cesare (although he and his father are both brought up several times throughout the entirety of the text) is Chapter VII: Concerning New Principalities Which Are Acquired Either By The Arms Of Others Or By Good Fortune. Cesare's career was seen to be a good example of this, since he started with the aid of King Louis XII of France who gave him (as part of the diplomatic maneuvering which also included a cardinal's hat for the king's advisor and a royal marriage for Cesare) a body of troops to command as he wished, provided he first aid him in his ventures in northern Italy. Cesare also became a ruler through fortune because it was his father's machinations that enabled him to attempt to create a state out of the Romagna in the first place. Machiavelli saw this as an opportunity handed to him not by dint of his abilities (although he also thought that Cesare was perhaps the most qualified man for the job) but because of the chance of his birth.
The difficulty, then, since Cesare became a prince through the arms of others and through good fortune, was making it so that he was not forced to rely on either of these things to hold on to his state. Machiavelli complimented Cesare's movement towards self-reliance by replacing Louis' men with his own and disarming or removing those "allies" who were waiting for the opportunity to take his gains for themselves, so that "when all the actions of the duke are recalled, I do not know how to blame him".
Machiavelli believed, however, that Cesare ultimately failed in his goal to create a state for himself since he was unable to hold on to it after Alexander VI's death. But unlike the other men he uses as examples, he cannot quite bring himself to put down on paper a simple formula describing where he went wrong and how another in his position could have succeeded. Instead he vacillates, changing his mind throughout the chapter on why Cesare was unable to maintain his grip on the Romagna. Machiavelli worked closely with Cesare for some time and greatly admired him even when Cesare's forces were threatening his beloved Florence. The Prince is written after Cesare's loss of power and after Machiavelli met with him in the depths of his despair and some of the tension in his writings reflects this fall of an idol (I should note that I'm not taking the text as satire--at least not the portions that deal with Cesare's specifically. This is because it does line up very neatly with what he had previously written about him in diplomatic dispatches that, presumably, were not meant to be satirical.). However, enough time has passed that the portrait Machiavelli paints in his text is not as bitter and disappointed as his letter to the Florentine government that depicted Cesare as a mad and broken man is, even if it is also not as (perhaps naïvely) exuberant and awed as his original impression was. There is still clearly a great deal of admiration being expressed, and Machiavelli eventually is forced to come to the still somewhat wistful conclusion that ultimately it was fortune that was responsible for Cesare's fall.
In canon, Cesare is not mature enough yet to really epitomize this prince, but he does certainly know promise. It is stated several times that he is very good at winning over people (this is much harder to accomplish in Camp where every third or fourth person has heard of the Borgia legacy) and he is clearly capable of moving behind the scenes. He already knows what he wants (although his idea of how to accomplish it differs somewhat from what eventually happens) and he is determined to achieve it. Cesare is aware that there are certain things he needs from people but he maneuvers the best he can so that he is not in a position where he is forced to rely upon them. Rather, they should be giving them to him as favors or to pay debts. The only people he truly leans upon are family and those who are intimate enough to be considered family, something that can be seen in his later life as well. Cesare understands that, at least at this point in his life, it is through the whim of his birth that he has the opportunities he does. At the same time, however, he is determined to do all he can to capitalize on this chance. If Fortune is a boat, he is already at the helm.