Often known as the "Hollywood three way." Guy collects cash from others, pockets it, pays the tab on his card and writes the whole meal off. (Probably bnot what your buddy was doing

)
Best way to handle those situations is to offer for you and the other guys to leave the tip...as in "OK...well we'll leave the tip. What's the tab? $40...so that's what, $3-4 from each of us?"
Wife is in the restaurant business. If you can't afford to tip, you can't afford to eat out.
Women parties are the worst...they'll break out calculators to get it down to the penny when splitting a tab.
And guys...round your tip up to the next dollar at least.
As far as calling him on it...fuggedaboudit. He neeeded to hear that. No biggie especially if it was in good humour.