Etymology
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free (adj.)

Old English freo "exempt from; not in bondage, acting of one's own will," also "noble; joyful," from Proto-Germanic *friaz "beloved; not in bondage" (source also of Old Frisian fri, Old Saxon vri, Old High German vri, German frei, Dutch vrij, Gothic freis "free"), from PIE *priy-a- "dear, beloved," from root *pri- "to love."

The sense evolution from "to love" to "free" is perhaps from the terms "beloved" or "friend" being applied to the free members of one's clan (as opposed to slaves; compare Latin liberi, meaning both "free persons" and "children of a family"). For the older sense in Germanic, compare Gothic frijon "to love;" Old English freod "affection, friendship, peace," friga "love," friðu "peace;" Old Norse friðr "peace, personal security; love, friendship," German Friede "peace;" Old English freo "wife;" Old Norse Frigg, name of the wife of Odin, literally "beloved" or "loving;" Middle Low German vrien "to take to wife," Dutch vrijen, German freien "to woo."

Meaning "clear of obstruction" is from mid-13c.; sense of "unrestrained in movement" is from c. 1300; of animals, "loose, at liberty, wild," late 14c. Meaning "liberal, not parsimonious" is from c. 1300. Sense of "characterized by liberty of action or expression" is from 1630s; of art, etc., "not holding strictly to rule or form," from 1813. Of nations, "not subject to foreign rule or to despotism," recorded in English from late 14c. (Free world "non-communist nations" attested from 1950 on notion of "based on principles of civil liberty.") Sense of "given without cost" is 1580s, from notion of "free of cost."

Free even to the definition of freedom, "without any hindrance that does not arise out of his own constitution." [Emerson, "The American Scholar," 1837]

Free lunch, originally offered in bars to draw in customers, by 1850, American English. Free pass on railways, etc., attested by 1850. Free speech in Britain was used of a privilege in Parliament since the time of Henry VIII. In U.S., in reference to a civil right to expression, it became a prominent phrase in the debates over the Gag Rule (1836). Free enterprise recorded from 1832; free trade is from 1823; free market from 1630s. Free will is from early 13c. Free school is from late 15c. Free association in psychology is from 1899. Free love "sexual liberation" attested from 1822 (the doctrine itself is much older), American English. Free and easy "unrestrained" is from 1690s.

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filibuster (n.)

1580s, flibutor "pirate," especially, in history, "West Indian buccaneer of the 17th century" (mainly French, Dutch, and English adventurers), probably ultimately from Dutch vrijbueter (now vrijbuiter) "freebooter," a word which was used of pirates in the West Indies in Spanish (filibustero) and French (flibustier, earlier fribustier) forms. See freebooter.

According to Century Dictionary, the spread of the word is owing to a Dutch work ("De Americaensche Zee-Roovers," 1678) "written by a bucaneer named John Oexmelin, otherwise Exquemelin or Esquemeling, and translated into French and Spanish, and subsequently into English (1684)." Spanish inserted the -i- in the first syllable; French is responsible for the -s-, inserted but not originally pronounced, "a common fact in 17th century F[rench], after the analogy of words in which an original s was retained in spelling, though it had become silent in pronunciation" [Century Dictionary].

In American English, from 1851 in reference to lawless military adventurers from the U.S. who tried to overthrow Central American governments. The major expeditions were those of Narciso Lopez of New Orleans against Cuba (1850-51) and by William Walker of California against the Mexican state of Sonora (1853-54) and against Nicaragua (1855-58).

FILIBUSTERING is a term lately imported from the Spanish, yet destined, it would seem, to occupy an important place in our vocabulary. In its etymological import it is nearly synonymous with piracy. It is commonly employed, however, to denote an idea peculiar to the modern progress, and which may be defined as the right and practice of private war, or the claim of individuals to engage in foreign hostilities aside from, and even in opposition to the government with which they are in political membership. [Harper's New Monthly Magazine, January 1853]

The noun in the legislative sense is not in Bartlett (1859) and seems not to have been in use in U.S. legislative writing before 1865 (filibustering in this sense is from 1861). Probably the extension in sense is because obstructionist legislators "pirated" debate or overthrew the usual order of authority. Originally of the senator who led it; the maneuver itself so called by 1893. Not technically restricted to U.S. Senate, but that's where the strategy works best. [The 1853 use of filibustering by U.S. Rep. Albert G. Brown of Mississippi reported in the Congressional Globe and cited in the OED does not refer to legislative obstruction, but to national policy toward Cuba.]

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penny (n.)

English coin, Middle English peni, from Old English pening, penig, Northumbrian penning "penny," from Proto-Germanic *panninga- (source also of Old Norse penningr, Swedish pänning, Danish penge, Old Frisian panning, Old Saxon pending, Middle Dutch pennic, Dutch penning, Old High German pfenning, German Pfennig, not recorded in Gothic where skatts is used instead), a word of unknown origin.

Offa's reformed coinage on light, broad flans is likely to have begun c.760-5 in London, with an awareness of developments in Francia and East Anglia. ... The broad flan penny established by Offa remained the principal denomination, with only minor changes, until the fourteenth century. [Anna Gannon, "The Iconography of Early Anglo-Saxon Coinage," Oxford, 2003]

The English coin was originally set at one-twelfth of a shilling (or 240 to a Tower pound) and was of silver, later copper, then bronze. There are two plural forms: pennies of individual coins, pence collectively. In Middle English, any coin could be called a penny, and in translations it rendered various foreign coins of small denomination, especially Latin denarius, whence comes its abbreviation d.

As an American English colloquial for cent, it is recorded by 1889. In reference to nails, "a pound," denoting that 1,000 nails will weigh so much, OED says it probably is based originally on the price per 100 and persisted as prices fell.

Penny-a-liner "writer for a journal or newspaper" is attested by 1830, from their supposed rate of pay. Penny dreadful in reference to "cheap and gory fiction" dates from 1870. Phrase penny-wise and pound-foolish is recorded from c. 1600.

Penny-pincher "miserly person" is recorded from 1906 (Middle English had pinchpenny (n.) in that sense; as an adjective penny-pinching is recorded from 1858, American English). Penny loafers attested from 1960, perhaps from the fashion of slipping a penny into the slits of the bands across the facing.

"A regular penny-a-liner is a person who supplies the newspapers of the city with short articles of news, ingenious remarks upon the current topics of the day, reports of meetings, or of cases in the police offices, accidents, &c. &c., but who, observe, has no express engagement from, or any direct connexion with, any newspaper whatever. His success is wholly precarious—always uncertain. If the contributions which those persons forward for publication, in this way, are published, they are certain of payment for them at the rate of one penny, three half-pence, and in rare cases, two pence a-line, according to the importance of the subject matter supplied. ["The London Penny-a-Line System," Irish Monthly Magazine, January 1833]
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K 

eleventh Roman letter, from Greek kappa, from Phoenician kaph or a similar Semitic source, said to mean literally "hollow of the hand" and to be so called for its shape.

Little used in classical Latin, which at an early age conformed most of its words (the exceptions had ritual importance) to a spelling using -c- (a character derived from Greek gamma). In Late Latin, pronunciation of -c- shifted (in the direction of "s"). Greek names brought into Latin also were regularized with a -c- spelling, and then underwent the Late Latin sound-shift; hence the modern pronunciation of Cyrus, Circe. To keep their pronunciation clear, the many Greek words (often Church words) that entered Latin after this shift tended to take Latin -k- for Greek kappa.

K- thus became a supplementary letter to -c- in Medieval Latin, used with Greek and foreign words. But most of the languages descended from Latin had little need of it, having evolved other solutions to the sound shifts.

K- also was scarce in Old English. After the Norman conquest, new scribal habits restricted -c- and expanded the use of -k-, which began to be common in English spelling from 13c. This probably was done because the sound value of -c- was evolving in French and the other letter was available to clearly mark the "k" sound for scribes working in English. For more, see C.

In words transliterated from Arabic, Hebrew, Turkish, Japanese, Hawaiian, etc., it represents several different sounds lumped. In modern use some of them are now with kh-; in older borrowings they often followed traditional English spelling and were written with a C- (Corea, Caaba, etc.).

As a symbol for potassium, it represents Latin kalium "potash." In CMYK as a color system for commercial printing it means "black" but seems to stand for key in a specialized printing sense. Slang meaning "one thousand dollars" is 1970s, from kilo-. K as a measure of capacity (especially in computer memory) meaning "one thousand" also is an abbreviation of kilo-.

As an indication of "strikeout" in baseball score-keeping it dates from 1874 and is said to represent the last letter of struck. The invention of the scorecard symbols is attributed to English-born U.S. newspaperman Henry Chadwick (1824-1908) principally of the old New York "Clipper," who had been writing baseball since 1858, and who explained it thus:

Smith was the first striker, and went out on three strikes, which is recorded by the figure "1" for the first out, and the letter K to indicate how put out, K being the last letter of the word "struck." The letter K is used in this instance as being easier to remember in connection with the word struck than S, the first letter, would be. [Henry Chadwick, "Chadwick's Base Ball Manual," London, 1874]
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dollar (n.)

"monetary unit or standard of value in the U.S. and Canada," 1550s, daler, originally in English the name of a large, silver coin of varying value in the German states, from Low German daler, from German taler (1530s, later thaler), abbreviation of Joachimstaler, literally "(gulden) of Joachimstal," coin minted 1519 from silver from mine opened 1516 near Sankt Joachimsthal, town in Erzgebirge Mountains in northwest Bohemia. German Tal is cognate with English dale. The spelling had been modified to dollar by 1600.

The thaler was from 17c. the more-or-less standardized coin of northern Germany (as opposed to the southern gulden). It also served as a currency unit in Denmark and Sweden (and later was a unit of the German monetary union of 1857-73 equal to three marks).

English colonists in America used the word dollar from 1580s in reference to Spanish peso or "piece of eight," also a large silver coin of about the same fineness as the thaler. Due to extensive trade with the Spanish Indies and the proximity of Spanish colonies along the Gulf Coast, the Spanish dollar probably was the coin most familiar in the American colonies and the closest thing to a standard in all of them.

When the Revolution came, it had the added advantage of not being British. It was used in the government's records of public debt and expenditures, and the Continental Congress in 1786 adopted dollar as a unit when it set up the modern U.S. currency system, which was based on the suggestion of Gouverneur Morris (1782) as modified by Thomas Jefferson. None were circulated until 1794.

When William M. Evarts was Secretary of State he accompanied Lord Coleridge on an excursion to Mount Vernon. Coleridge remarked that he had heard it said that Washington, standing on the lawn, could throw a dollar clear across the Potomac. Mr. Evarts explained that a dollar would go further in those days than now. [Walsh]

Phrase dollars to doughnuts "an assured thing, a certainty" (such that one would bet a dollar against a doughnut on it) is attested by 1884; dollar diplomacy "financial imperialism, foreign policy based on financial and commercial interests" is from 1910.

The dollar sign ($) is said to derive from the image of the Pillars of Hercules, stamped with a scroll, on the Spanish piece of eight. However, according to the Bureau of Engraving and Printing of the U.S. Department of the Treasury:

[T]he most widely accepted explanation is that the symbol is the result of evolution, independently in different places, of the Mexican or Spanish "P's" for pesos, or piastres, or pieces of eight. The theory, derived from a study of old manuscripts, is that the "S" gradually came to be written over the "P," developing a close equivalent of the "$" mark. It was widely used before the adoption of the United States dollar in 1785.
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