I know you're new in town, so you probably don't have a good feel for the whole dynamic yet. But small towns can also mean years of old wounds, and even the small ones can hurt, so be careful about things that seem like jokes...because sometimes they're not.
You don't have to apologize to me. It only hurts me because it hurts Kent. And apologizing to Kent will probably make him uncomfortable. Not saying you shouldn't do it anyway, but fair warning. DMs are probably better than in person.