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Shenanigans, or shenanigan, also with several variant spellings, can be dated to 1855 USA in both the OED and Etymonline, but the OED simply says "Origin obscure" and Etymonline throws a few guesses into the ring:

Suggestions include Spanish chanada, a shortened form of charranada "trick, deceit;" or, less likely, German Schenigelei, peddler's argot for "work, craft," or the related German slang verb schinäglen. Another guess centers on Irish sionnach "fox."

Can anyone provide anything more concrete?

(Note: Another question asks specifically about “I call shenanigans” but not shenanigans itself.)

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Here's a second 1855 reference: to a "Shananigan ditch" dug in gold mining country in California in 1855. "On the first day of June, 1855, the defendants constructed two ditches, called respectively Rasin and Shenanagan Ditches, draining the waters of Todd's Valley Ravine, about one-half mile above the head of plaintiffs' ditch, and thereby diverting and depriving the plaintiffs of the waters that flow down said ravine." –  Peter Shor Dec 19 '13 at 4:58
    
It's actually a 1858 court case, but it's clear from this that the word was in use with its current meaning in 1855. –  Peter Shor Dec 19 '13 at 5:20
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It seems clear to me from the timing and location of the OED's citations and my discovery above that the word was coined (or popularized) in the 1849 California Gold Rush, an event which created ample opportunity to use the word. The ethnic make-up of California at the time would then argue for the Spanish origin. –  Peter Shor Dec 20 '13 at 13:32
    
Excellent links @PeterShor! No use prior, and then 'boom' everywhere, and always in archtypal context... Theory: In your "second 1855 reference", the ditch is actually dug in 1850. The name 'Shenanagan' is capitalised and used consistently like it's a valid (albeit alternate) name. Later references in NYTimes refer to it in quotes, like an the name of an archetype for 'claim deception'. It's also used in the singular. I can't see a smoking gun yet, but I suspect it's an actual alternate name to the Nevada Water Co's Bicknell ditch coming into use before the case was heard but after deception. –  shermy Dec 21 '13 at 3:30
    
Singular, exemplar(?) use. "...suspected, in the classic language of the times, that there was something of "shenanigan" in it." Yankee-notions, Volume 4, Issues 1-12 (T. W. Strong, 1855) –  shermy Dec 21 '13 at 3:32
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2 Answers

Wentworth & Flexner, Dictionary of American Slang (1960) suggests an extended Irish term:

shenanigans n.pl. Tricks, pranks, nonsenses; petty cheating or deception. Since c1870; may be from the Irish "sionnochwigham" = I play tricks.

The same source lists "shenanannygag" (also meaning a trick or prank) as being based on shenanigans and "not common."

Chapman & Kipfer, Dictionary of American Slang, Third Edition (1995) bump the origin to "by 1855" and retain the Wentworth/Flexner suggestion that the word perhaps comes from sionnachuighim "play tricks, be foxy."

The Facts on File Dictionary of Word and Phrase Origins (1997) begins its entry with this sentence:

shenanigans. Though now it is always used in the the plural, this Americanism for "mischief" or "trickery" was first recorded as shenanigan in 1855 in California.

I suspect that the citation in question involves a story from the California Herald cited in numerous Google Books periodicals, such as this one from the Merchants' Magazine and Commercial Review, volume 40 (1859), in which the following sentence occurs:

Jim took his bill, and eyeing the puzzled landlord as though he suspected some "shenanigan," he broke out—

"I want to see them 'ar books."

The earliest Google Books occurrence of this anecdote is in Yankee-notions, vol. 5 (1856), but unfortunately the snippet view of this version of the story doesn't include the relevant term within its window.

ADDED TO ANSWER (1/3/14):

Not surprisingly—considering its date of publication—John Russell Bartlett, Dictionary of Americanisms (1848) doesn't include an entry for shenanigan or shenanigans. But I was somewhat surprised that the second edition of this book (1859) has no such entry either. I haven't been able to find a copy of the third edition. The fourth edition (1877) does have shenanigan, along with this interesting discussion of the equivalence of shenanigan, skullduggery, and hornswoggle:

The "Philadelphia Times" (Nov. 5. 1877), in defining the word skullduggery [which Bartlett calls "a very good and very common word in the West"], says, "Its best Eastern equivalent is shenanigan, although the less complicated word hornswoggling [which Bartlett also identifies as "Western"] rather directly translates it."

This quotation suggests that shenanigan had become popular enough in the Eastern United States by 1877 for Easterners to consider it commonplace in (and perhaps even native to) their region.

Another early discussion of shenanigan (though spelled with a fourth n) occurs in Maximilian Schele De Vere, Americanisms: The English of the New World (1872):

Shenannigan, probably a purely fictitious word (though a Dutch origin has been claimed for it), frequently heard in the South and West, and denoting groundless bragging for the purpose of getting the better of another. "Shenannigan means any kind of chaff, foolery, nonsense, advanced to cover some little scheme or game." Hence Miss Vinnie Ream, the artist, whose skill was said to have been largely measured by her personal charms, was recently admonished by a writer in the Chicago Evening Post to "go to work and try better next time, instead of fooling members of Congress by a pair of black eyes and a mass of beautiful curls. No shenannigan, Vinnie!" (January 1871.)

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Thanks for this. Where Google tempts, Hathi Trust provides (left column, just below image caption). –  Hugo Dec 31 '13 at 9:43
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Wentworth & Flexner clearly don't know their Irish. Sionnochwigham is utterly bungled up. The form used later on, sionnachuighim, would be the proper one. Presumably the English word should then be from the person-neutral present form sionnachuigheann, except that's pronounced /SHUN-uh-xee-un/ (excuse the ad hoc notation; typing IPA on a phone doesn't work), which audibly lacks both an n and a g compared to the English word. –  Janus Bahs Jacquet Dec 31 '13 at 11:58
    
Good efforts... Certainly no better to offer atm, but the use still seems consistent with archetypal idea (referring to a deception via the ditch, perhaps - or the incident of supposed trickery). Wish there was something more concrete earlier. Seems strange that Bicknell et al might call a contentious dig (a ditch diverting water from other sites) 'Shenanagan' if it had any negative or deceitful connotation. Currently looking along native american etymological routes... (as in 'river through the spruces', shenandoah... but most likely wrong language, group, etc –  shermy Jan 1 at 12:34
    
... (continued) probably clutching at straws. An old map of the area in question would be best showing the Nevada Water Co interests + Marius Ravine... but no joy so far. –  shermy Jan 1 at 12:35
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For the record, now I’m back on my computer, the proper IPA for sionnachuigheann (modernised spelling would be sionnachaíonn, though it’s not included in De Bhaldraithe’s Irish-English dictionary) would be, approximately, [ˈʃʌnˠɤˌxɰ͡iː(ə)n], with a reversal of primary and secondary stress in some southern and western dialects. –  Janus Bahs Jacquet Jan 1 at 13:09
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This word is commonly used in the UK, and my Irish friend says its origin is from Erse (Irish Gaelic), spelt differently, but meaning the same thing - tricksy, fox like, etc. There is no proof of this, but it is a fact that many Irishmen working as navvies were present in California at the time this word appeared in the States.

UPDATE: Original gaelic Irish word 'sionnachuighm' meaning to play tricks - rough pronunciation at that time 'shinnuckeem'.

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