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It still would be good to start the same way. a fear of being leashed will turn into a fear of the leash because they will pick up on the pattern of the leash being picked up= leash being put on. And the better a reward history he has with the leash the easier it will be to put it on him...

I would start even smaller then that even! First step would be to show him the leash reward and reward him, keep the leash at a distance from him where he is aware of it but not showing any major signs of stress. If at any point in training he does show any major signs stop the session and next...