Karim Sadjadpour sees Khamenei as following Niccolo's playbook. But it might not be enough:
However cunning, it's impossible to escape the fact that Khamenei is a 72-year-old leader who hasn't left the country since 1989, presiding over a population where nearly 70 percent are under the age of 33 and connected to the world via satellite TV and Internet. Whether or not not he manages to die as supreme leader is an open question. But the gap between Khamenei and Iranian society has become unbridgeable, and only maintainable via coercion and Machiavellian power politics. Despite his vast authority, his public appearances increasingly render him less a supreme leader than a grouchy old man yelling at his youthful subjects to stay off his proverbial lawn.
Khamenei's inflexibility has so far served him well. His unwillingness to bend, however, has made it more likely that the Islamic Republic itself will have to break. As a young advisor to opposition leader Mehdi Karoubi recently told me, "We don't want a revolution; we've seen how it turns the country upside down. But they're giving us no other choice."
The Dish 