Hugo Chavez, the president of Venezuela who died in 2013, was his country's leader for 15 years. He maintained power as president longer than any other democratically elected ruler in either North or South America, according to the Washington Post. Since Machiavelli's The Prince is primarily about how a leader holds onto power, Chavez's long rule raises the question of how Machiavellian—how immorally pragmatic or morally upright—he was.
The Prince upended previous thinking about leadership which rested on the idea that a moral ruler was inherently a wise and effective ruler. Instead, Machiavelli argued that behaving morally could work against a ruler's ability to stay in power and that the end—power—justified the means of its maintenance. Perception, he argued, was more important than reality, and a ruler needed to appear moral rather than be moral. However, no matter the importance of appearing moral, appearing strong was of utmost importance to staying in power because it intimidated enemies. Ruthlessness could work as a virtue and not as a vice. Furthermore, a successful ruler had to pay attention to the interests of the common people.
We know that Chavez was ruthless in denouncing his enemies; for example, he called Catholic priests "devils in vestments." He also bragged about intimidating his enemies, saying he made "oligarchs tremble."
Critics and supporters agreed that he made the needs of the poor a top priority. Whether he did this from Machiavellian instincts or genuine conviction, it helped him maintain popularity and power in a way Machiavelli might have approved.
The most important way in which Hugo Chavez exemplifies the ideas from The Prince is in the fact that he seems to care about nothing other than holding on to power. His goal is not necessarily to make Venezuela strong or to keep its people happy. Instead, his goal is to remain in power and he will do whatever he thinks will accomplish this.
The other ways in which Chavez exemplifies the ideas contained in the book all flow from this first similarity. Many of the things that Chavez does to remain in power are very similar to what Machiavelli says a prince should do. For example, a prince should understand that people can essentially be "bought" with favors and help. This is what Chavez seems to have done with the poor of Venezuela. He has bought their loyalty with all sorts of programs meant to help them.
Chavez's actions all appear to be based on maintaining his hold on power, not on helping his people or following what we would see as good ways of governing. This is essentially what Machiavelli tells rulers they should do.