Etymology
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dictator (n.)
Origin and meaning of dictator

late 14c., dictatour, "Roman chief magistrate with absolute authority," from Old French dictator and directly from Latin dictator, agent noun from dictare "say often, prescribe," frequentative of dicere "to say, speak" (from PIE root *deik- "to show," also "pronounce solemnly").

In Latin, a dictator was a judge in the Roman republic temporarily invested with absolute power; this historical sense was the original one in English. The transferred sense of "absolute ruler, person possessing unlimited powers of government" is from c. 1600; that of "one who has absolute power or authority" of any kind, in any sphere is from 1590s. 

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dictatorship (n.)

1580s, "office or term of a (Roman) dictator," from dictator + -ship. The sense of "absolute authority" evolved by late 17c.

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dictatorial (adj.)

1701, "pertaining to a dictator; absolute, unlimited;" see dictator + -ial. Meaning "imperious, overbearing" is from 1704. Related: Dictatorially. Earlier in the sense "pertaining to a dictator" were dictatorian (1640s); dictator-like (1580s). "Dictatorial implies, on the one hand, a disposition to rule, and, on the other, a sharp insistence upon having one's orders accepted or carried out." [Century Dictionary]

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Hitler 
used figuratively for "a dictator" from 1934.
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generalissimo (n.)

"supreme military commander," 1620s, from Italian generalissimo, superlative of generale, from a sense development similar to French general (see general (n.)). Parson Weems applied it to George Washington. In 20c. use sometimes from Spanish generalísimo in reference to the military dictator Franco.

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caudillo (n.)

dictator in Spain or Latin America, 1852, from Spanish caudillo, cabdillo "leader, chief," from Late Latin capitellum, diminutive of caput (genitive capitis) "head" (from PIE root *kaput- "head"). Originally South American; in Spain taken as a title by Franco (1938) in imitation of German Führer, Italian Duce.

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cunctator (n.)

"one who delays or lingers," 1650s, from Latin, agent noun from cunctari "to be slow, hesitate, delay action," from PIE *konk- "to hang" (source also of Hittite kank- "to hang, weigh," Sanskrit sankate "is afraid, fears," Gothic hahan "to leave in uncertainty," Old English hon "to hang," Old Norse hengja "to hang, suspend;" see hang (v.)). In Roman history the famous surname of dictator Q. Fabius Maximus. Related: Cunctation "delay," 1580s.

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dight (v.)

Middle English dighten, "to adorn," from Old English dihtan "dictate, appoint, ordain; guide; compose, set in order," an early borrowing from Latin dictare "to dictate" (see dictate (v.)).

The Latin word was borrowed earlier into continental Germanic, where it became Old High German dihton "to write compose," German dichten "to write poetry." It was so nativized in late Old English that it was used to gloss Latin dictator. In Middle English, dight exploded to a vast array of meanings (including "to rule," "to handle," "to abuse," "to have sex with," "to kill," "to clothe," "to make ready," "to repair") till it was one of the most-used verbs in the language, but all its senses have faded into obscurity or survive only in dialectal or poetic use.

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