Etymology
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runt (n.)

c. 1500, "old or decayed tree stump" (Douglas), a provincial word of unknown origin. The meaning was extended to "small ox or cow," especially of the breeds characteristic of Wales and the Scottish Highlands (1540s, if indeed this is the same word), and by 1610s generally to undersized animals and ignorant people.

The slang sense of "person of low but thick-set build; a stocky, stunted person," a term of abuse, is by 1700. The  sense of "smallest of a litter" (especially of pigs) is attested from 1841 as a Shropshire word, though it seems to have become general in American English. Some see a connection of runt, at least in the "animal" sense, to Middle Dutch runt "ox," but OED thinks this unlikely, and pronounces the word "of obscure origin." Related: Runty (1807); runtish (1640s).

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page (n.2)

"youth, lad; boy of the lower orders; personal servant," c. 1300 (early 13c. as a surname), originally also "youth preparing to be a knight" (beneath the rank of a squire), from Old French page "a youth, page, servant" (13c.), possibly via Italian paggio (Barnhart), from Medieval Latin pagius "servant," perhaps ultimately from Greek paidion "boy, lad," diminutive of pais (genitive paidos) "child."

But OED considers this unlikely and, with Century Dictionary, points instead to Littré's suggestion of a source in Latin pagus "countryside," in sense of "boy from the rural regions" (see pagan). Meaning "youth employed as a personal attendant to a person of rank" is first recorded mid-15c.; this was transferred from late 18c. to boys who did personal errands in hotels, clubs, etc., also in U.S. legislatures.

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outside (n.)

c. 1500, "outer side, the exterior part or surface of a thing," from out- + side (n.). Meaning "the part or place that lies without or beyond an enclosure or barrier" is from 1610s. In isolated regions of the globe it tends to mean "the world of civilization and settlement" (1827); in prison (and army) slang, "the world outside prison (or the army)," by 1903.

The adjective is attested from 1630s, "being on the outside; to the outer surface or boundary;" as "situated or operating outside (the house, the system, etc.) by 1841; as "not directly concerned or interested" by 1881. As an adverb from 1813 "on the outside, on or to the exterior;" as a preposition from 1826. Colloquial phrase outside of "with exception of" is from 1859. Outside chance "very unlikely chance" is by 1845, originally in horse racing (see outsider).

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G.I. (adj.)
also GI, 1936 as an adjective meaning "U.S. Army equipment," American English, apparently an abbreviation of Government Issue, and applied to anything associated with servicemen. Transferred noun sense of "U.S. Army soldier" arose during World War II (first recorded 1943), apparently from the jocular notion that the men themselves were manufactured by the government.

An earlier G.I. (1908) was an abbreviation of galvanized iron, especially in G.I. can, a type of metal trash can; the term was picked up by U.S. soldiers in World War I as slang for a similar-looking type of German artillery shells. But it is highly unlikely that this G.I. came to mean "soldier." No two sources seem to agree on the entire etymology, but none backs the widespread notion that it stands for *General Infantry. GI Joe "any U.S. soldier" attested from 1942 (date in OED is a typo).
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gherkin (n.)
small cucumber used for pickling (either a small, prickly type of cucumber produced by a certain plant (Cucumis anguria), or a green or immature common cucumber), 1660s, from early modern Dutch gurken, augurken (late 16c.) "small pickled cucumber," from East Frisian augurk "cucumber," probably from a Balto-Slavic source (compare Polish ogórek "cucumber," Lithuanian agurkas, Russian oguretsŭ), possibly ultimately from Medieval Greek angourion "a kind of cucumber," which is said to be from Persian angarah [Klein, etc.], but OED seems to regard this as unlikely. A Dutch source says the Greek is from a word for "immature" and that the vegetable originated in northern India and came to Eastern Europe via the Byzantine Empire.

The Dutch suffix is perhaps the diminutive -kin, though some regard it as a plural affix, with the Dutch word mistaken for a singular in English. The -h- was added 1800s to preserve the hard "g" pronunciation.
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bail (n.1)

"bond money, security given to obtain the release of a prisoner," late 15c., a sense that apparently developed from that of "temporary release (of an arrested person) from jail" (into the custody of another, who gives security for future appearance at trial), which is recorded from early 15c. That seems to have evolved from the earlier meanings "captivity, custody" (late 14c.), "charge, guardianship" (early 14c.).

The word is from Old French baillier "to control, to guard, deliver" (12c.), from Latin baiulare "to bear a burden," from baiulus "porter, carrier, one who bears burdens (for pay)," which is of uncertain origin; perhaps it is a borrowing from Germanic and cognate with the root of English pack, or perhaps from Celtic. De Vaan writes that, in either case, "PIE origin seems unlikely."

To go to(or in) bail "be released on bail" is attested from mid-15c. In late 18c. criminal slang, to give leg bail meant "to run away."

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curse (n.)

late Old English curs "a prayer that evil or harm befall one; consignment of a person to an evil fate," of uncertain origin. No similar word exists in Germanic, Romance, or Celtic. Middle English Compendium says probably from Latin cursus "course" (see course (n.)) in the Christian sense "set of daily liturgical prayers" extended to "set of imprecations" as in the sentence of the great curse, "the formula read in churches four times a year, setting forth the various offenses which entailed automatic excommunication of the offender; also, the excommunication so imposed."  Connection with cross is unlikely. Another suggested source is Old French curuz "anger."

Meaning "the evil which has been invoked upon one, that which causes severe trouble" is from early 14c. Curses as a histrionic exclamation ("curses upon him/her/it") is by 1680s. The curse in 19c. was the sentence imposed upon Adam and Eve in Genesis iii.16-19. The slang sense "menstruation" is from 1930. Curse of Scotland, the 9 of diamonds in cards, is attested from 1791, but the signification is obscure.

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orator (n.)

late 14c., oratour, "an eloquent or skilled speaker; one who pleads or argues for a cause," from Anglo-French oratour (Modern French orateur) and directly from Latin orator "speaker," from ōrare "to speak, speak before a court or assembly, pray to, plead."

This is sometimes said to be  from PIE root *or- "to pronounce a ritual formula" (source also of Sanskrit aryanti "they praise," Homeric Greek are, Attic ara "prayer," Hittite ariya- "to ask the oracle," aruwai- "to revere, worship").  But according to de Vaan, the Latin word is rather from Proto-Italic *ōs- "mouth," from PIE *os- "mouth" (see oral). He writes:

The chronology of the attestations shows that 'to plead, speak openly' is the original meaning of orare .... The alternative etymology ... seems very unlikely to me: a connection with Skt. a-aryanti 'they acknowledge' and Ru. orat' 'to shout', since nothing suggests a meaning 'to shout' for the Latin verb, nor does it seem onomatopoeic.

The general meaning "public speaker," is attested from early 15c. Fem. forms were oratrice (early 15c., from Anglo-French); oratrix (mid-15c., from Latin); oratress (1580s).

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last (adj.)

c. 1200, "latest, final, following all others," a contraction of Old English latost (adj.) "slowest, latest," superlative of læt (see late); in some uses from late (adv.). Cognate with Old Frisian lest, Dutch laatst, Old High German laggost, German letzt.

Meaning "last in space, furthest, most remote" is from late 14c.; meaning "most unlikely or unsuitable" is from mid-15c. Meaning "most recent, next before the present" (as in last night, last September) is from late 14c.; latest would be more correct, but idiom rules and the last time I saw her might mean the most recent time this hour or the final time forever.

The biblical last days ("belonging to the end") is attested from late 14c. Last hurrah is from the title of Edwin O'Connor's 1956 novel. Last word "final, definitive statement" is from 1650s. A dying person's last words so called by 1740. As an adjective, last-minute attested from 1913. Last-chance (adj.) is from 1962. Expression if it's the last thing I do, expressing strong determination, is attested by 1905.

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pillar (n.)

c. 1200, piler, "a column or columnar mass, narrow in proportion to height, either weight-bearing or free-standing," from Old French piler "pillar, column, pier" (12c., Modern French pilier) and directly from Medieval Latin pilare, from Latin pila "pillar, stone barrier," a word of unknown etymology. The figurative sense of "prop or support of an institution or community" is recorded from early 14c. Related: Pillared.

In medieval architecture often made so as to give the appearance of several shafts around a central core; "by architects often distinguished from column, inasmuch as it may be of any shape in section, and is not subordinated to the rules of classic architecture" [Century Dictionary].

Phrase pillar to post "from one thing to another without apparent or definite purpose" is attested from c. 1600, late 15c. as post to pillar, mid-15c. as pillar and post; but the exact meaning is obscure. Earliest references seem to allude to tennis, but post and pillar is recorded as the name of a game of some sort c. 1450. The theory that the expression is from pillar as the raised ground at the center of a manège ring around which a horse turns is unlikely because that sense seem to date only to 18c.

The Pillars of Hercules are the two hills on opposite sides of the Straits of Gibraltar, Abyla in Africa and Calpe in Europe, said to have been torn asunder by Hercules.

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