Are there any records of ancient people looking for the misdirect in a prophecy?

Question

Ancient prophecies, especially those of ancient Greece and the Oracle of Delphi, were famously tricky. There are dozens of stories of great leaders being tripped up by double-meanings and misinterpretations, usually to their own destruction.

Now, obviously hindsight is 20/20, but some of those twists and tricks seem painfully obvious to modern audiences. For example, when the Oracle tells you "If you go to war, a great empire will be destroyed," even a schoolchild will recognize that that might be your empire, rather than the enemy's...

And yet, over and over, great leaders and terrible generals misinterpret their prophecies, and go to meet their doom. Which fits wonderfully with the ancient preoccupation with hubris, so I'm sure they had no problem with it as they retold the story, but it does raise the question:

Did any ancient prophecy-seekers recognize the tricky nature of prophecies, and make decisions or take action based on the possibility that the Oracle's words may have more than one meaning? Do we have any records of people trying to outsmart the Oracle?

Answer 1

The Wikipedia page of "oracular statements from Delphi" lists a few accounts that might apply here. One example could be the Oracle of Delphi's counsel to Philip of Macedonia. He was told, "With silver spears you may conquer the world." The straightforward reading would be to make a whole bunch of spears made of silver and go to war. But Philip wisely decided to take control of nearby silver mines and use their wealth to bribe away his enemies' allies.

As for "outsmarting" the Oracle, Philip's son Alexander the Great is the clearest example. Originally, she refuses to answer his question of whether or not he would conquer the world. In response, Alexander began dragging her by the hair, and which point she screams "No more! You're unbeatable!" Satisfied with her answer, he leaves.

But probably the best example is from Plato's Apology. Socrates' friend poses the question to the Oracle, "Is there any man alive wiser than Socrates?", to which the Oracle straightforwardly answered "None." Socrates, rather than accepting the praise, tries to divine out the true meaning of the prophecy:

When I heard the answer, I said to myself, What can the god mean? and what is the interpretation of this riddle? for I know that I have no wisdom, small or great. What can he mean when he says that I am the wisest of men? And yet he is a god and cannot lie; that would be against his nature. After a long consideration, I at last thought of a method of trying the question. I reflected that if I could only find a man wiser than myself, then I might go to the god with a refutation in my hand. I should say to him, "Here is a man who is wiser than I am; but you said that I was the wisest."

Socrates then goes and interrogates men society considered wise, but finds their wisdom lacking. In the course of his investigation, he finally understands the prophecy: Socrates is the wisest man alive, because he is the only one who recognizes how little he actually knows.