Not sure what your work history has to do with anything but whatever.

If a guy grabs my bags and starts waking away from me and I don't want to tip him, I stand there and motion him to bring the bags back and I take them from there.

It sounded to me like he grabbed your bags and you willingly followed him only to then realize that it wasn't that long of a trip. To me, you tacitly agreed to tip him when you followed him willingly without protest.

That's just how it works and you should know that (IMHO).

I seriously doubt that this guy is suffering from a sense of entitlement. Yes, he's trying to scam you in the sense that it's hard for you to say no when he's already got your bags but it's also not really a con when everyone knows the game.