Lorenzo de Medici wants to know if Machiavelli would be a good advisor and if I would recommend hiring him. Why or why not?

The life of Machiavelli (1469-1527) overlapped with that of Lorenzo de Medici (1449-1492), though Machiavelli held office as the Secretary of the Second Chancery of the Republic of Florence from 1498 to 1512, when the Medici were not in power. Lorenzo de Medici had to contend with several rival factions during his rule over the Republic of Florence, and Machiavelli's The Prince was written for the new type of ruler, like Lorenzo de Medici, who had to establish power and force to rule over a stable state. Lorenzo de Medici had to quell insurrections, and during the Pazzi Conspiracy in 1478, the rival Pazzi family, supported by Pope Sixtus IV, tried to assassinate Lorenzo and his brother and co-ruler, Giuliano. Lorenzo de Medici survived the attack, while his brother was killed, and Sixtus IV demanded that Lorenzo be turned over to him in the aftermath of the event (in which members of the church were killed). Lorenzo de Medici eventually presented himself to Ferdinand I of Naples, the Pope's ally. As a result, Lorenzo forged a situation of peace. 

This type of diplomacy made Lorenzo a well-loved leader, and he furthered his hold on power by strategic marriages and by becoming a generous patron of the arts to people such as Leonardo da Vinci, Michelangelo, and Botticelli. In this way, Lorenzo de Medici's ability to consolidate and hold onto power used some of Machiavelli's techniques, in that Lorenzo realized that he had to find new methods to consolidate his power.

However, Lorenzo de Medici's success as a leader and his popularity arose not out of fear, as Machiavelli suggested with his advice that it is better to be feared than to be loved as a leader. Instead, Lorenzo de Medici was a benevolent and generous leader. Machiavelli, on the other hand, advised leaders to generate the reputation of generosity but not to be truly generous, as they would use up their resources. Lorenzo de Medici was also admired as a man of the arts, as he wrote poetry. Therefore, Lorenzo de Medici's power in part stemmed from his personal attributes, including his generosity, intelligence, and courage (for example, his willingness to submit himself to Ferdinand I), rather than from his ability to generate fear. Perhaps Machiavelli would not be the best advisor to such a leader, as Machiavelli's methods of using fear and immoral tactics, if necessary, to consolidate power were not what Lorenzo de Medici used to become a popular and powerful leader of the Republic of Florence.