Hyphens, En Dashes, Em Dashes

Q. Hello, my question concerns hyphenating the term “anti-Second Amendment.” Wherever I see it, it is hyphenated as in my first sentence, but if the purpose of the hyphen is to let the reader know which of the words are linked, then “anti Second-Amendment” would seem to make more sense. But my spelling checker flags this alternate hyphenation. Is this an instance where we would be justified breaking the rule?

A. First, capitalized proper nouns are rarely hyphenated. The job of a hyphen is to link two words. The capital letters in a proper noun do that job very well; a hyphen is usually overkill. Second, Chicago style does not use a hyphen to link a prefix (like anti-) to an open compound. We require an en dash (anti–Second Amendment), because a hyphen would link only anti and Second, leaving us with an amendment that is “anti-Second.”