I also get a bit of side-eye when the case cite is older. Yes, I know - sometimes you want to cite to the OG - but I like to cite to a current case - because it shows it is still good law.
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Or just cite to NYT v. Sullivan - THE MOST FAMOUS DEFAMATION CASE EVER
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I cite to older law if it is still good law (not overturned, modified); states the legal point I'm making; and doesn't otherwise harm my client. Newer cases may be better, but there are many older cases that set the standard. For defamation, NY Times v Sullivan is the seminal case for defamation.
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