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Saul Cornell on Originalism's Historical Challenges
Michael Ramsey

At the Ohio State University site Origins: Current Events in Historical Perspective, Saul Cornell (Fordham): Originalism’s Historical Problems: The Supreme Court’s Embrace of a Controversial Theory.  Some excerpts:

[I]nterpreting a constitution is different from what historians do when they make sense of other old legal documents, such as wills, contracts, or statutes. Nor can one simply run the text of the Constitution through something like a Google translator function: a fact most originalists have failed to grasp. 

Words, particularly the words of a constitution, are embedded in a rich range of contexts when they are uttered. Recovering their original meaning requires restoring not just the text but paying close attention to the contexts in which those words would have been interpreted.

In contrast to those other more familiar legal texts, the U.S. Constitution was the product of a collective effort, so discerning a single intent as a guide to its meaning is hard to do, if not impossible. Additionally, from the moment it was adopted, there were bitter disagreements over what type of text the Constitution was and how it ought to be interpreted. 

The Constitution was a new type of document with no clear precedents or agreed-upon methods for interpreting its meaning. Was the Constitution like a Parliamentary statute, or more like a contract between the people and their government? The former uses one set of legal principles and the latter a different set of tools.

Within months of its adoption, former Anti-Federalists—opponents of the unamended Constitution—and Federalists were already arguing bitterly over what the text meant. Alexander Hamilton and James Madison, two of the co-authors of The Federalist, the contemporary commentary on the Constitution they published, disagreed over almost every major constitutional question that emerged during the turbulent decade after ratification. If people at the time could not agree on a single meaning of the text, it seems unlikely that judges in the 21st century can find one.  

Other originalists have argued that the Constitution should be read like a recipe that needs to be followed precisely as one would in cooking a meal. Originalists, however, don’t appear to have spent much time in the kitchen. Real cooks seldom follow recipes strictly and any cook worth their salt would adjust a recipe on the fly to deal with the actual situation they faced in the kitchen. If you opted for a tough cut of meat, such as brisket, you would certainly opt to cook the stew a bit longer. Speaking of salt, most recipes typically end with the advice “season to taste,” so different cooks are likely to interpret that advice in light of their own experiences in the kitchen and distinct culinary traditions.

If the entire Constitution contained precise instructions, the recipe analogy might work better. But most parts of the text are not precise at all. Much of the document was deliberately crafted with open-ended language, both to allow the government to address unprecedented challenges and because compromise during the drafting of the document meant using ambiguity and vagueness in a strategic fashion, kicking many practical questions down the road to later generations. ...

It's a good survey of challenges to originalism from a historical perspective.  Originalists need to have responses to these and related points (but I think responses are available).