Well then, it’s no wonder you like coming here!
Just a joke.
In the Roman period, it has to be St Augustine! A truly extraordinary mind. A choice of Latin author outside the Roman period would be St Thomas Aquinas. Better still would be to get these two together and just listen… and drink in great draughts of genius…
What I would do to hear these two compare and contrast their respective approaches, and all in Latin too.
We can always dream and for that let us be thankful.
Sean
And a good one!
I was once on a jury where the barrister acting for the defence had obviously styled himself on a mixture of Cicero and Rumpole of the Bailey. I hadn’t studied much Cicero at that stage, but as soon as I did, I thought of that barrister. I don’t think the guy on trial had a chance with that defence! (Not to mention a great deal of rather damning evidence!) But I can’t make too many lawyer jokes as we have two in our family (but 3 psychologists, which may say something about our family!) Cicero may just have met his match with some of our own windbags! 
You could just as easily have said, “takes one to know one!” (And, I’m afraid, just as accurately.)
David
Wow, what a great - and extremely difficult to answer - question!
Several names pop into my mind:
-How about Tertullian? I bet he could get you entertained for a night or two! One of the most invective men I have read, gotta say. Just ask if he’ll take you to the Roman colosseum and see what he says…
-Vergil: definately on the top of my list, though I hope he wouldn’t go on about his Aeneis and how much better he’d want it to be… I’d just ask him to recite some of his Bucolics or Georgics, sit back and enjoy..!
-Lucretius would be someone I could definately have a bunch of conversations with. An extremely gifted poet and philosopher, I bet we could talk for days on end. (and I don’t buy the stories of him being that depressed, either)