Etymology
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freebooter (n.)

1560s, loan-translation of Dutch vrijbuiter "plunderer, robber," from vrijbuiten "to rob, plunder," from vrijbuit "plunder," literally "free booty," from vrij "free" (from Proto-Germanic *frijaz, from PIE root *pri- "to love") + buit "booty," from buiten "to exchange or plunder," from Middle Dutch buten, related to Middle Low German bute "exchange" (see booty).

The English word, Danish fribytter, Swedish fribytare, and German Freibeuter were formed on the model of the Dutch word, which is the source of filibuster (q.v.). The back-formed verb freeboot is recorded from 1590s. Related: Freebooting; freebootery.

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*pri- 

prī-, Proto-Indo-European root meaning "to love." In some languages (notably Germanic and Celtic) it developed derivatives with the sense "free, not in bondage," perhaps via "beloved" or "friend" being applied to the free members of one's clan (as opposed to slaves).

It forms all or part of: afraid; affray; filibuster; Frederick; free; freebooter; freedom; friend; Friday; Frigg; Godfrey; Geoffrey; Siegfried; Winfred.

It is the hypothetical source of/evidence for its existence is provided by: Sanskrit priyah "own, dear, beloved," priyate "loves;" Old Church Slavonic prijati "to help," prijatelji "friend;" Welsh rhydd "free;" Old English freo "exempt from; not in bondage, acting of one's own will," Gothic frijon "to love," Old English freod "affection, friendship, peace," friga "love," friðu "peace," Old Norse Frigg, name of the wife of Odin, literally "beloved" or "loving."

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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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rapparee (n.)

"Irish freebooter," 1690, originally "pikeman," a kind of soldier prominent in the war of 1688-92, from Irish rapairidhe, plural of rapaire "half-pike."

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Rob Roy (n.)

Highland freebooter and folk hero, Robert Roy MacGregor (1671-1734). His name means "Red Robert." Scott's novel first was published in 1817. As a type of cocktail made with Scotch whiskey, it is attested from 1960.

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hussar (n.)
"light-cavalryman," 1530s, from German Husar, from Hungarian huszár "light horseman," originally "freebooter," from Old Serbian husar, variant of kursar "pirate," from Italian corsaro (see corsair). The original Hussars were bodies of light horsemen organized in Hungary late 15c., famed for activity and courage and elaborate semi-oriental dress. They were widely imitated elsewhere in Europe, hence the spread of the name.
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brigand (n.)

c. 1400, also brigaunt, "lightly armed irregular foot-soldier," from Old French brigand (14c.), from Italian brigante "trooper, skirmisher, foot soldier," from brigare "to brawl, fight" (see brigade). Sense of "robber, freebooter, one who lives by pillaging" is earlier in English (late 14c.), reflecting the lack of distinction between professional mercenary armies and armed, organized criminals.

Probably then it was in the sense of skirmishers that the name of brigand was given to certain light-armed foot-soldiers, frequently mentioned by Froissart and his contemporaries. ... The passage from the sense of a light-armed soldier to that of a man pillaging on his own account, is easily understood. [Hensleigh Wedgwood, "A Dictionary of English Etymology," 1859]
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corsair (n.)

"government-sanctioned freebooter of the seas," 1540s, from French corsaire (15c.), from Provençal cursar, Italian corsaro, from Medieval Latin cursarius "pirate," from Latin cursus "course, a running," from currere "to run" (from PIE root *kers- "to run"). The sense of the Medieval Latin verb evolved from "course" to "journey" to "expedition" to an expedition specifically for plunder. As "a privateering pirate ship" from 1630s.

The name in the languages of the Mediterranean for a privateer; chiefly applied to the cruisers of Barbary, to whose attacks the ships and coasts of the Christian countries were incessantly exposed. In English often treated as identical with pirate, though the Saracen and Turkish corsairs were authorized and recognized by their own government as part of its settled policy towards Christianity. [OED]
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jayhawker (n.)

"freebooter, guerrilla," American English, 1858, originally "irregular or marauder during the 'Bleeding Kansas' troubles" (especially one who came from the North). It seems to have come into widespread use only during the Civil War. There was said to have been a bird of this name, but evidence for it is wanting. Perhaps a disparaging use from jay (n.). Hence back-formed verb jayhawk "harass" (1866).

Bushwhackers are men, united together, but not soldiers, who live in the bush; and whose avowed object is to kill every Union soldier they can, and cripple, so far as they can, the resources of the Federal military power. The jayhawkers are thieves. They plunder indiscriminately from all parties. In the same band are both rebel and Union men. ... Guerilla bands are companies enlisted and sworn into the rebel service; but not belonging to the armies. [Henry M. Painter, "Brief Narrative of Incidents in the War in Missouri," Boston, 1863.]
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moss (n.)

the meanings "mass of small, cryptogamous, herbaceous plants growing together" and "bog, peat-bog" are the same word: Old English meos "moss plant" and mos "bog;" both are from Proto-Germanic *musan (source also of Old High German mios, Danish mos, German Moos), also in part from Old Norse mosi "moss, bog," and Medieval Latin mossa "moss," from the same Germanic source.

These are from PIE *meus- "damp," with derivatives referring to swamps and swamp vegetation (source also of Latin muscus "moss," Lithuanian mūsai "mold, mildew," Old Church Slavonic muchu "moss"). The Germanic languages have the word in both senses, which is natural because moss is the characteristic plant of boggy places. It is impossible to say which sense is original. The proverb that a rolling stone gathers no moss is suggested from 14c.:

Selden Moseþ þe Marbelston þat men ofte treden. ["Piers Plowman," 1362]

Moss-agate "agate stone with moss-like dendrite forms (caused by metallic oxides)" is from 1790. Scott (1805) revived 17c. moss-trooper "freebooter infesting Scottish border marshes" (compare bog-trotter).

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