City folk truely amaze me at times, it's like they pull their head out of the sand every once in a while and say "Hey, what's going on around here? You shouldn't do it that way. I know more than you." Absolutely ridiculous.
You may have already tried this, but the first thing I would do is tie a knot in the lead rope right outside of the halter. (just remember to tie a new knot every so often as his head grows! lol)
Secondly, if he is broke to tie really well and will stand all day without putting up much of a...