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I'm interested in the origin of the term smooth operator. Does anyone know where it came from? What kind of operation?

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In a non-mathematical sense, I presume? –  Peter Taylor Oct 3 '11 at 12:43
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Oh great, now I've got the Sade song stuck in my head. Thanks a heap. –  Daniel Roseman Oct 3 '11 at 13:39
    
Do you think it could be associated with Jacob in the bible book of Genesis. He swindled his brother, and Scripture refers to himself as a "smooth Man." I'm not suggesting that Jacob called himself a "con-man," but perhaps this descriptive title "smooth operator" came from this. –  user43606 May 2 '13 at 17:46
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The word operator has had several slang meanings over time, according to the Oxford English Dictionary. A brief list of the time and definition of operator is:

1598: A person who performs a surgical operation or operations; an operating surgeon or dentist.

1611: A person who deals in quack medicines, etc. Obs.

1704: A person who commits fraudulent operations; a thief, a pickpocket.

1828: A person who carries on (speculative) financial operations. Also: a person adept at speculative or shrewd operations; (formerly) a person who acts in a cunning or underhand manner.

1838: A person who or company which runs a business, enterprise, etc.

1944: A person with a talent for seduction; a smooth talker.

The phrase smooth operator starts to appear in the late 1890s. For example, in "The Strange Schemes of Randolph Mason", it says:

Here, a smooth operator is someone who is "smooth" at running a business or set of financial operations (the senses from the earlier 1800s). This is not the only application of smooth operator. In the 1980s, the OED notes the following usage:

1980 Photo-Love Summer Spectacular 7/1 You're quite a smooth operator, what with names and telephone numbers just like that!

The "operation" has changed over time. In the 1700 and 1800s, the "operation" was financial--it referred to either theft operations, speculating on stocks (operate as a verb meant "To deal or speculate in stocks or shares; to buy and sell commodities as a broker"), or business operations. Then, in the 1900s, the "operations" referred to the "business" of playing at courtship and seducing women.

Thus, now a smooth operator can refer to the "business" of financial operations or seduction operations, with smooth modifying operator in a primarily (and possibly solely) negative way.

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The OED’s earliest citation for those actual words is dated 1980. However, a 1944 citation has 'Big-time operator, a slick chick's smooth fellow', itself a quotation from a slang dictionary of the time. Chambers Slang Dictionary defines ‘operator’ alone as ‘a successful seducer of women’ and dates it to the 1940s.

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Google Books shows examples from 1896 –  JoseK Oct 3 '11 at 12:08
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From the movie The Best Years of Our Lives. Al is talking to his daughter about Fred and refers to him as a smooth operator. Google it.

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