U got balls man, def.
A wise conductor that spots your grift could cause trouble.
I know a metro-north conductor. Generally a nice guy, probably would let you slide if you forgot your cash one day and were up-front about it. If you messed with him though he would definitely call transit cops on you, bc he would take it personal.
Check out an older Cusack film, The.Grifters, some classic moves in that flick