Shylock After the Trial by John Gilbert (late 19th century)Does the word shyster—meaning "one who is professionally unscrupulous especially in the practice of law or politics"—contain anti-Semitic connotations?
To be sure, the word lacks anti-Semitic origins. Yet in order to answer the question, we should consider not only its denotation, which is a word's dictionary definition, but also its connotation, or its innuendo.
As contributors to Wikipedia observe, "The term—possibly because of its vaguely Yiddish sound—is sometimes mistaken to connote Jewishness." Another source of confusion is undoubtedly the character Shylock, the Jewish usurer and antagonist in Shakespeare's Merchant of Venice.
But you don’t have to be a descriptivist to acknowledge that language evolves. This is not to affirm the use of, say, "disinterested" to mean "uninterested"—we can and should draw the line at Standard English, and dismiss such double standards. Rather, it behooves educated people to remember that all words carry cultural baggage.
In this way, a statement from the editors of the New York Observer makes sense: in an essay on “shyster” a few years ago, they noted that the word "has traditionally been loaded with anti-Semitism.”
Finally, consider this parallel. In 1999, David Howard, then the head of the D.C. Office of the Public Advocate, lost his job for advising coworkers—in a conversation about finances—not to be “niggardly," which means "miserly" and bears no racial denotations whatever. The problem? Howard is white and his coworkers are black; and even though Howard was gramatically correct in his use of the word, his choice was tactless.
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