A lawyer and an elderly man were seated next to each other on a long flight—maybe to Chicago, maybe to Tel Aviv, who knows.

The lawyer quickly sized him up and figured the older gentleman looked a bit too simple, maybe even easy to take advantage of. He thought it might be fun to entertain himself at his expense.

“Sir,” the lawyer said, “let’s play a little game. It’ll pass the time.”
The older man was tired. He just wanted to rest, so he politely declined.

But the lawyer wouldn’t let it go.

“It’s simple,” he insisted. “I’ll ask you a question. If you don’t know the answer, you pay me five dollars.

Then you ask me one. If I don’t know it, I’ll pay you five hundred. Deal?”

The old man stroked his beard, thought for a moment, then nodded.
“Alright. Let’s play.”

The lawyer went first:
“What’s the distance from the Earth to the Moon?”

Without saying a word, the old man pulled out five dollars and handed it over.

Now it was his turn.

“What goes up a hill on three legs… and comes down on four?”

The lawyer froze. He opened his laptop, started searching online, digging through every source he could find—Wikipedia, forums, even texting colleagues from law school. An hour passed. Nothing.

Finally, frustrated and defeated, he nudged the old man awake and handed him $500.

The older man calmly tucked the money into his pocket, leaned back, and closed his eyes again.

But the lawyer couldn’t let it go. He tapped him on the shoulder.

“Alright, come on… what’s the answer?”

The old man yawned, shrugged, reached into his pocket, pulled out five dollars… and handed it back.

Then he closed his eyes—and went right back to sleep.