Yes, Chase had a broken carnassial tooth (those mega-huge pre-molars). We hadn't a clue and while I'm not a big tooth brusher here either, I don't think I'd have seen it anyway. I took him one time because of some swelling below one eye. The vet checked him and she didn't see a broken tooth or abscess either, she said he needed a drain placed in the cheek bump and antibiotics. About 8-12 months later, with no recurrence of that little swollen area on his cheek, his breath got really, horribly bad. He got his teeth actually cleaned then and during the cleaning they found the big premolar on that side was broken and gave him a course of antibiotics. They said if the smell came back, take him to a dental specialist. For humans, a broken tooth would be terribly painful so I wasn't going to wait and see what happened- the tooth wasn't going to repair itself. I took him to a dental vet right away. His tooth was broken and there was an abscess. Based on reading about abscesses, I'm pretty sure that swollen place on his cheek months earlier was related to a tooth abscess, not mucositis, as the vet originally suggested.
Anyway, he had the tooth removed and that was all pretty uneventful. I had to put his food into a little food processor and whiz it into pretty fine crumbs and mix it with water for a week or 2. The vet said even soft, canned food could have too much texture and could dislodge the clot or cause problems with the stitches. They said they don't really recommend any hard chew items, no raw bones, no Nylabones, nothing hard or rigid. At the post-op follow up visit, the dentist said not to give anything that I can't bend by hand and that even retriever rolls can allow them to clamp down hard enough to break teeth. I do offer him the big retriever rolls but he rarely chews them these day. I let them chew dehydrated sweet potato chips and smaller rawhide flip chips. They could chew things like pigs ears or tracheas although I haven't tried those.
These dogs are so tough, not showing pain when things must surely hurt, try not to feel too bad about not finding it sooner. Chase must have had that broken tooth for over a year and was still eating, chewing bones and sticks, acting normal from a mouth standpoint. I hope Finn's extraction goes smoothly. Even though the tooth is so large, you'd never know Chase had his pulled. He still chews sticks and tree bark even if he isn't that interested in his big fat retriever rolls any longer.