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This position helped him get to know what other leaders were like in person and not just what they seemed to be.
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When the Medici family returned to power they didn't trust him.
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He was put in jail and tortured for being a suspect of conspiring against the Medici family.
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The Prince was about how a leader should act and rule their land.
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When the Medici family where finally driven out of Florence Machiavelli had passed away.
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Machiavelli's book was published five years after his death. Only popes, church leaders, nobles, and royalty.
