This may need a trip to the vet. The nail protects something called the quick, a fleshy growth that extends partially into the nail. If the nail is broken to the point that the quick is exposed, he is in pain and at risk for infection. When my dog broke off his nail in the threshold of a doorway, my vet gave me a choice of muzzling and holding him really tight and plan on struggling to get my dog to come see him ever again or putting him under which is riskier and more costly... in order to clean and trim back the quick. I chose to muzzle and hold but was never able to return to the care of that vet as my dog's memory of it was just too vivid. Too bad since he was such a great vet. Wash his foot with water or hydrogen peroxide and have a look. Do so carefully and watch yourself with your dog's instinct to bite while in pain. If you can see the quick, take him in.
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