That has always been a back and forth question and everyone will have different opinions on the matter. You can always get him a breakaway halter which will come right off if he gets it caught on something, instead of hanging him up.
Secondly, I would work with him on being caught instead of running away from you. Carry the halter around with you whenever you are around him so that it becomes a natural thing for him to see. Than, if you go out to catch him (give yourself some time, don't rush it), advance and retreat. See how close he lets you get, even if it is just a couple of feet. Talk to him, hum, sing, whistle, whatever to keep his focus on you, but avoid eye contact as he is a prey animal and only predators make eye contact. If his body language tells you he is going to flee, than stop and take a step back. Do that one step at a time, back and forth, until he lets you near him. When he does, pet him and than walk away, don't even try to halter him at that point. This is just showing him that he doesn't have to run away from you.
A few minutes later, go back out and start it all over again. It might go faster, it might go slower, it might go the same, but either way, take your time and be patient. This time, slip his halter on, but put the rope around his neck first so that he doesn't bolt. You might have to do this several times, but it will be worth it in the end when you have a horse who comes to you instead of running away. Good luck!