Originally Posted by
MileHighGuy
That question is over the line, I def would have replied "how do you afford your underwear on a TSA salary" or something better if I could come up with it on the spot. (and if he replied he makes a decent salary, I'd have followed up with "That's a shame, they shouldn't pay more wasted tax dollars than minimum wage on stupid questions." It's none of their business who is paying for, or how you're paying for your travel. If they think you're running drugs, then check your bags

Except that the USICS/CBP/Immigration guys aren't TSA. So you'd be making a bit of a fool of yourself.
I had an immigration guy in MCO ask me several times about how much money I was carrying and then refer me to secondary. Most likely because I was completing my second PTY/MEX run in 6 weeks, but still annoying. At least the person at secondary was more friendly about it.