Cattle dogs are very smart dogs and can learn alot of amazing things. You say you rescued him last Aug so maybe it is something his previous owner taught him. I have tried to teach Dash and Jazz and am working on Dazzle but don't think they quite understand but they will stop at a street and wait to be released to cross. I don't think they understand it has anything to do about cars though.
I do have to wonder if after looking both ways and seeing a car coming would Chester wait for it to pass or would he be like so many people these days and go ahead and cross telling himself he is the pedestrian and has the right of way and thus step in front of the car ? ( his lawyer ready to sue the person that runs him over!)