With his position as the son of the Pope and his ambition to united Italy, Cesare Borgia is an excellent historical character to view in terms of how someone like him could be used in a role playing game. Many RPGs, including fantasy, post apocalyptic, and even science-fiction, often have some type of 'Border Kingdoms' where the right person with the right backing and the right timing and fortune, can make of themselves something new that rivals the old powers.
So how would someone like Cesare be used?
1. Patron: This is the most obvious use of a character like Cesare. Much like Griffith from the anime and manga Berserk, Cesare is going to need "feet on the ground" to do things that he himself might not be able to do, or should be seen doing.
1a. Assassination: There is a specific political opponent that needs to be eliminated.
1b. Kidnapping: In order to insure compliance of some allies, some children will need to be kidnapped.
1c. Liberation: Say you have a target that is necessary to acquire and in most instances, would willingly ally with you, but hey, the enemy boss used a little of that 1b and now the characters have to go and free those taken hostage.
1d. Defend the Fort: During his imprisonment, one of the only things that kept Cesare alive, was his forts manned by his loyal commanders, could not be taken. The players could be those commanders.
1e. Spies: One of the strengths Cesare had, was not in his actual military commanding or his own personal fighting ability. No, rather, it was his tight grip on accurate and recent news. He was able to take advantage of his enemies ignorance and use shock and awe techniques and often didn't have to strike a single blow.
1f. Scouts: While similar to the above, it's more of an outdoor thing. In the Borgias series, Cesare is able to take a fortress without a lengthy siege by discovering its weakness. In history, Cesare used speed of troop to navigate his forces where they were not expected to be. Players could be the ones scouting out passes, mountain trails, and other routes that haven't been in use for years or creating new routes specifically for the soldiers.
1g. Strategic Targets: In one of the various Troll Slayer novels about Felix and Gortex, the pair are in city under siege. Some of the weapons being used to bring death and destruction and demonic siege weapons. Gortex takes battle axe in hand and goes out in a sneak attack mission to cripple those weapons and give the city further time to repel the invasion.
2. Enemy: What happens if Cesare is on the opposite side of the characters and how would that happen if he's been using them?
2a: An Example Must Be Made: One of the things Cesare did was kill one of the harsh commanders that inflicted discipline on the newly formed barony. He did this in order to assuage the fear and loathing that the common people had of the man, and the forces he belong to. By killing that commander, Cesare was able to lift the people's spirits and able to insure that the people were loyal to him.
2b: It's a Mistake: One of the keys of drama is misunderstood circumstances. Imagine that the players are relaxing at City A when their master's chief enemy comes into the city unknown to them. Would you believe that it was a coincidence? Or what if one of the player character's has a relative that starts working against the player character's patron?
2c: Cost Savings: Well, I know that I agreed to pay you X, but it's simply easier to kill you at this point. One of the problems with working with unscrupulous individuals is that there often comes that moment of "curse you for your sudden but inevitable betrayal."
2d: Player Strikes Back: If the players are powerful enough, they may decide that this setting yourself up as a baron and ruler isn't a bad idea and go against their patron before the nobles even know what hit them.
When looking at patrons, allies, and enemies, there are many options that the GM should consider and how those elements may play out. For example, suppose that none of the above happen, but when a new official of some importance is elected, either religious, criminal, or military, and they say, "We're now turning our eye to your patron. If you're there, you will not be."
Cesare for example, did very well while his father the Pope was still alive. But when the Pope died and Cesare's enemy became pope? It was all over for a large number of people. The players have to decide if they want a last man standing showdown that they can't win or wash their hands of the whole thing.
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