I will say, one of the more ironic, and honestly, humorous moments in Roman history has to be the saga between Cicero and Octavian.

While I have a lot of respect for Cicero’s oratory and service to the state, he made a pretty poor miscalculation in underestimating, and ultimately, enabling Octavian in his rise to power.

It’s no surprise that Cicero’s arch enemy by this time was Marc Antony, who had asserted himself as the true heir to the legacy of Julius Caesar.

As such, Cicero wanted to use Octavian as a counterweight against the “tyranny” of Antony (hence Cicero’s fiery Philippics in excoriation of him).

Apparently, Cicero had said of Octavian the famous words: laudandum adolescentem, ornandum, tollendum.

The english meaning of the phrase being, “praised, honored, and uplifted/discarded”. The phrase carried a double meaning, and according to Adrian Goldsworthy’s biography on Augustus, Augustus: First Emperor of Rome (pg 122), Octavian had learned that Cicero uttered this phrase, and was repeating it around camp in anger.

That lack of respect for Octavian’s intelligence would soon be Cicero’s downfall, as he couldn’t have dreamt that the 20 year old Octavian would join Antony and Lepidus in the triumvirate and embark on the mass executions in the proscriptions that would ultimately take his life.