Etymology
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rob (v.)

late 12c., robben, "steal, take away (from someone) unlawfully; plunder or strip (a place) by force or violence," from Old French rober "rob, steal, pillage, ransack, rape," from West Germanic *rauba "booty" (source also of Old High German roubon "to rob," roub "spoil, plunder;" Old English reafian, source of the reave in bereave), from Proto-Germanic *raubon "to rob" (from PIE *runp- "to break;" see corrupt (adj.)).

Lord, hou schulde God approve þat þou robbe Petur, and gif þis robbere to Poule in þe name of Crist? [Wyclif, c. 1380]

To rob the cradle is attested from 1864 in reference to drafting young men in the American Civil War; by 1949 in reference to seductions or romantic relationships with younger persons. Related: Robbed; robbing.

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robbery (n.)

c. 1200, robberie, "the act, practice, or occupation of stealing or plundering," from Old French roberie "robbery, theft," from rober "to rob" (see rob).

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rubato 

musical instruction in reference to shifting time-values of notes, 1883, Italian, short for tempo rubato, literally "robbed time," from past participle of rubare "to steal, rob" (see rob (v.)).

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rubble (n.)

"rough, irregular stones broken from larger masses," especially "waste fragments from the demolition of a building, etc.," late 14c., robeyl, from Anglo-French *robel "bits of broken stone," which is of obscure origin, apparently related to rubbish "waste fragments" [OED], but also possibly from Old French robe (see rob). Middle English Compendium compares Anglo-Latin rubisum, robusium.

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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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robber (n.)

late 12c., "one who commits robbery, one who steals, plunders, or strips unlawfully by violence," from Anglo-French robbere, Old French robeor, agent noun from rober "to rob, steal, pillage, ransack, rape" (see rob).

Robber baron in the "corrupt, greedy financier" sense is attested from 1870s, from a comparison of Gilded Age capitalists to medieval European warlords (the phrase is attested in the historical sense from 1831).

It is the attempt of the more shrewd to take advantage of the less shrewd. It is the attempt of the strong to oppress the weak. It is the old robber baron in his castle descending, after men have planted their crops, and stealing them. [Henry Ward Beecher, sermon, "Truthfulness," 1871]
Regulation by combination means that the railroad managers are feudal lords and that you are their serfs. It means that every car load of grain or other produce of your fields and shops that passes over the New York Central shall pay heavy toll for right of transit to Vanderbilt, the robber baron of our modern feudalism, who dominates that way. [W.C. Flagg, testimony to Congress, 1874]
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robe (n.)

"long, loose outer garment reaching almost to the floor, worn by men or women over other dress," late 13c., from Old French robe "long, loose outer garment" (12c.), from a Germanic source (compare Old High German rouba "vestments"), from West Germanic *raubo "booty" (cognate with Old High German roub "robbery, breakage"), which also yielded rob (v.).

Presumably the notion is of fine garments taken from an enemy as spoil, and the Old French word had a secondary sense of "plunder, booty," while Germanic cognates had both senses; as in Old English reaf "plunder, booty, spoil; garment, armor, vestment."

The meaning "dressing gown" is from 1854; such extended senses often appear first in French, e.g. robe de chambre "dressing gown," robe de nuit "nightgown." From c. 1300 in reference to official vestments and thus indicative of position or membership in a religious order, guild, etc.; metonymic sense of The Robe for "the legal profession" is attested from 1640s.

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despoil (v.)

c. 1200, despoilen, "rob, plunder, ravage;" c. 1300, "strip off" (clothes, armor, etc.); from Old French despoillier "to strip, rob, deprive of, steal; borrow" (12c., Modern French dépouiller), from Latin despoliare "to rob, despoil, plunder," from de- "entirely" (see de-) + spoliare "to strip of clothing, rob," from spolium "skin, hide; arms, armor; booty" (see spoil (v.)). Related: Despoiled; despoiling.

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reave (v.)

Middle English reven "to rob plunder," from Old English reafian "to rob (something from someone), plunder, pillage, take away by force or stealth," from Proto-Germanic *raubōjanan "to rob, deprive of" (source also of Old Frisian ravia, Middle Dutch roven, Dutch rooven, Old High German roubon, German rauben), from PIE *runp- "to break" (see corrupt (adj.)).

Related: Reaved; reaving. Now obsolete or archaic or dialectal only. The old past participle was reft. Also compare bereave. OED reports that the forms reive, rieve, originally Scottish, were sometimes used "when the reference is to the taking of goods or cattle by force," hence reiver, reiver, etc., e.g. "The Reivers," Faulkner's novel.

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highwayman (n.)
"one who travels the highways with intent to rob people" (often on horseback and thus contrasted to a footpad), 1640s, from highway + man (n.).
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