Why Caligula may have been Rome's greatest Emperor

No doubt this idea deserves a lengthier discussion than I can provide here.  Just based on a cursory read of Suetonius and a semester of Roman history in college, paired with a lifelong interest in modern politics, I think Caligula has suffered from a common problem; history is written by the winners.  He sought early to endear himself to the political establishment, but turned on them and sought to destroy the power and control structures he came to regard as oppressive.  That he was assassinated should make the fact that he was a threat to the establishment self-evident, but the victors were successfully able to spin his behavior as madness, cruelty, and wanton unprovoked violence.  Caligula's image as crafted by those who hated him (and killed every member of his family, for good measure) is hardly helped by the crappy pornographic movie made to illustrate his reign in the 1970s.

If one reads Suetonius as a skeptic, realizing how modern political opponents portray each other in the worst possible light, Caligula takes on the color of a profound reformer.  The historical record shows Caligula was his predecessor's plaything at any early age, and grew up in an environment where he was exposed to the worst of the Roman system and aristocratic oppression.  At some point he was taken under the wing of Tiberius, as opposed to simply being his toy, who then showed young Caligula the political ropes.  Upon the death of Tiberius, the Senate heaped titles and power on Caligula to ingratiate themselves with him.  Caligula probably believed the leading citizens of Rome thought well of him and truly embraced him, given the arc of his childhood abuse, and he returned their generosity.  Then he got sick.

No doubt without a chosen successor or heir, Caligula's family and political allies jostled for position while the rumors flew that he was near death.  The extended illness would have allowed plots to rise and fall, contingency plans made and broken.  When he unexpectedly recovered and took the lay of 
the land, he saw the sycophants, political opportunists and power hungry for what they were.  He may have even thought he'd been poisoned.  He saw that greed was what motivated the leading elite, and was disgusted.

In response to the collapse of the illusion he lashed out.  He made a political statement with the joke about appointing his horse Consul, he killed political enemies and took the source of their family power--inherited wealth.  He took on the military by humiliating them at the English channel, he took on the temples and religious authorities. Yet the average Roman citizen had nothing to fear from him.  he never pulled a poor person out of a crowd and had him killed just for pleasure; he instead often gave Romans large sums of money and held many entertaining and extravagant games to please them.  He surrounded himself not with slaves with whom he could do as he wished, nor rich elites, but freed slaves, men and women he had liberated from bondage.

As the plots against him grew, he realized the only way he could be free to remake the political, economic and social structures of Rome would be to move the Capitol off the Italian peninsula.  Alexandria, established as a center of knowledge in the ancient world by the Ptolemies, provided the answer; Roman Senators were forbidden by law to travel there, and the aristocratic elites would have to upset their political power structures and generations of tributes and favors to move there.  It was not madness but necessity that drove Caligula to want to move the Capitol of the Empire to Egypt.  It was less a symptom of Caligula's illness, more a sign of someone who wanted to destroy the establishment.  This threat was a step too far, and Caligula was assassinated for it.  And not just he but everyone else who could succeed him was killed, with the exception of one, who was named Emperor by the guard in a power grab in defiance of the aristocratic elites who plotted the attack.  As rumors of his death spread, rather than joy in the streets history records average Romans turned out in droves and held vigil at Caligula's palace.  This is not the sign of a man as hated by the public as he was by the aristocrats who profited from the inequities of the Roman system and were victims of his reign.

It was those aristocrats, and the puppet of the Praetorian Guard who succeeded him, who wrote the  historical record of that era.