Yes, trying to hurt somebody's ego would indeed be a pretty good example of humiliating them.
Look, if you think that the bound booklet of $2 bills is a fun gag, there's a humane and lighthearted way to do it. You use the bills as described, but if somebody seems even a bit uncomfortable with them you volunteer an explanation for what's going on. That way they actually have a cool story to tell. And the joke's on you, not them.
But that is not what Woz did. He intentionally made himself as suspicious as possible, in multiple ways, just to try to force people to investigate. It was all about showing his superiority over this sad loser working a 10-hour shift in a suit, who thought he knew a thing or two about counterfeit money. Well, he wasn't all that, and Woz sure showed him who the smartest guy in the room was.
> Thankfully, if these people go unchallenged then when they go off it's on a random unsuspecting person. He's prepared and can take it in stride.
No unsuspecting person would have this interaction in the first place. They would not have gone through the trouble of arranging for legit money to look counterfeit. That is not what normal people do. They would not have a script to follow to string people along, and carefully consider just what the optimal level of dodgy behavior would be. They would not waste others' time for their own amusement. Because that's not what people with even a pinch of empathy would do.
Put yourself into some work situation. I don't know, maybe you're a engineer given this is HN. And you get this bug report from a customer. It's really well written, has a screenshot showing the issue, and includes reproduction steps. You try to reproduce it, and can't. So you ask some questions from a customer, iterate a few times, add some logging statements and ask them to reproduce the problem. etc. And then finally the customer smugly says that there never was a bug. They photoshopped the screenshot, and made everything up. If you'd actually known how this program works, you'd have known that this bug could never exist. It's a hilarious gag, what a prankster! And you were paid for this work, no harm done, right?
No. Fuck that. I would be furious at having my time wasted like that. And this is what Woz did. Not just once, but probably dozens of times. That's just outright sociopathic behavior, and I cannot believe how many people here are defending it just because he is a member of your tribe.