I'm confused by the initial comparison between Hamilton and XKCD > Alexander Hamilton was against the Bill of Rights, particularly the First Amendment. This famous xkcd comic explains why: They seems to be saying very different things: Hamilton (as I understand it) is saying the First Amendment is unnecessary (and even dangerous) because the constitution already provides no power by which to regulate speech. XKCD, ho…
The XKCD comic myopically references the 1st Amendment for the promotion of simplistic authoritarianism. Whereas without an explicit 1st Amendment, Freedom of Speech would have been forced to be held generally by society, rather than making for a legalistic red herring.
Alternatively, Freedom of Speech could have simply vanished. A good way of addressing that question would be to look look for rights that the Founders held as obvious, yet were not codified - how did they fare over time?
IMO the entirety of the Constitution suffers from the same basic flaw wherein the Founders did not foresee layered-complexity creating contradictions. This is understandable, given they preceded Gödel.
For example - "the accused shall enjoy the right to a speedy and public trial". Yet by actually trying to exercise this right today, you mortally up the ante of your charges. To me, this seems like a failing test case.