At the time the 14th amendment went into force, and at the time Wong Kim Ark was decided, native American tribes were considered sovereign nations, located within the US but having separate laws and governments (which is why the US would sign treaties with them). I guess it would be akin to being from San Marino or Lesotho, where your country is entirely within the borders of another country. With the Indian Citizenship Act of 1924, Congress declared native Americans born within the US to be citizens of the USA by birth, so that old interpretation has been overtaken by events. His father is a US citizen, so no. And in any case, the language of these EOs is forward looking, so they couldn't take citizenship from anyone who currently has it. Absolutely - you can't use an Executive Order to change the constitution.
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