I dislike the genre that purports to be a conversation between people who are long dead and modern figures. The author can always dictate the result of the debate and make the loser look bad. I recently saw one at Aleteia between GK Chesterton and white nationalists. Guess who won? I don't doubt that GKC would have held his own quite nicely against any number of such figures, but the exchange was frankly not-credible. Chesterton would say this, you see, and the the white nationalists would say that, which GKC would counter with this. They would attempt to catch him up along the lines of A, which he would have to agree with, being deeply respectful of national cultures, but he would see them coming and make a distinction B that they hadn't anticipated and finally rout them entirely by pointing out C.
I didn't actually read the article. I'm betting I came close.
Things are a bit better with imagined conversations between contemporaries, but that's not going to be ultimately fair either. I have loved Peter Kreeft's Between Heaven and Hell, A Dialogue Somewhere Beyond Death with John F. Kennedy, CS Lewis, and Aldous Huxley (who died within hours of each other in 1963). Kreeft tries very hard to be fair, but he clearly favors Lewis, and CSL does seem to carry the day at the end, though Kreeft doesn't rub it in or get triumphalist. Huxley finishes second, I think. I still recommend the book, even if you are one who would prefer someone other than Lewis win, because Kreeft really works at being fair, as I said. But don't consider the final implied victory a done deal. Plus, the book's short and cheap. That's nice.
His second work, about Socrates discussing abortion, is less successful, I think because it has that ancient-modern mix that is more inherently unfair.
I know these imagined conversations don't turn out to be true because I have been having them in my head for sixty years, forever arguing with hundreds of other people. He'll say this and I'll agree that it's partially true but point out that, to which he will respond with this claim and this one, this one, and that one, but hahahaha! I will then say Fourscore and Seven Years Ago, and To Thine Own Self Be True, and They-sewed-fig-leaves-together-and-made-themselves-aprons! He will be dumbfounded. Overwhelmed. He will gape, and gasp!
Then I will actually have the argument and the other person says nothing like that at all. They will pursue a line I had not expected.