I’m no expert on Cicero and I have no real firm concept of the man, but I think you are perhaps making a mistake judging him on the Philippics. Bear in mind that these were written by a man, late in life, after seeing everything he believed in fall to pieces. He had a long political career behind him, full of compromises, disappointments, and having to give in on his principles far more than he ever got in return. Is it any wonder that he was full of venom and spite?

He longed desperately for someone who could restore the Republic, and so he consistently pinned his hopes foolishly on whoever looked strong enough to carry out that task and seemed disposed towards actually doing so. That would be why he fell for Octavian’s line of BS. Plus, Cicero had never trusted Antony and knew just how violent and dangerous the man was. Small wonder he held back from confronting Antony face to face; he knew exactly what it would get him (and ultimately did). Namely, dead.

Sure, he sucked up to Caesar and snarked about him behind his back, but I think he actually found something in Caesar that appealed to him and just never understood that they might have been able to work together. What you see as hypocrisy, I see as ambivalence.

To understand Cicero, I think you have to follow his writings from the beginning to see how his character changed over the years. The petty, venom-spewing suck-up who only kicks powerful men when they are down is also the man who began his career by standing up to Sulla (by proxy). And remember, too, that the nature of political discourse in Rome had changed drastically from Cicero’s youth. What had once been dignified debate in the senate had become verbal warfare, occasionally spilling over into physical violence. (I leave it to the reader to find a parallel with some young idealist of his or her own political stripe who came to Washington 30 or 40 years ago and today argues through name-calling and demonization – like everyone else on the Hill.)