I have three conditions for pulling these moves

Early or mid game I need a strong draw. Mid-game up until five players left I need to have a big stack. On the bubble, I'll do this a lot more with four players, one of whom is a short stack. Same applies to hands agaisnt chip leader / second stack if there's a shorty ITM with us.

Most of the time however, I prefer bluffing with continuation bets or raising weak flop bets. It just makes things simpler. When I raise a flop bet, the guy almost always has to have a made hand to come over the top or call.

I just don't think a bluff is worth it here. About half the time, the big stack is trapping here and the other half they took a stab and checked it. Even if they took a stab with air, a smaller bet would be just as likely to take the pot.

My first thought after reading his hand was that players at the 22s just aren't smart enough for stuff like to pay off in the longrun. (You're the one named "Rationality," here. This guy is still getting giggles from "69.")

From the index card of poker wisdom hanging above my computer:

"Don't project your knowledge onto other players."
"Pass up marginal situations."
"Maintain your edge."
"Don't get fancy - EVER!"