middleman n.

Old English middel, "equally distant from extremes or limits; intermediate," from Proto-West Germanic *midla- (source also of Old Frisian middel, Old Saxon middil, Middle Low German, Dutch middel, Old High German mittil, German mittel), from Proto-Germanic *medj, from PIE root *medhyo- "middle."

Middle finger "the third finger" (counting the thumb as the first)  so called from late Old English. Middle school is attested from 1838, originally "middle-class school, school for middle-class children;" the sense in reference to a school for grades between elementary and high school is from 1960. Middle management, the level below senior management, is by 1941.

Middle-of-the-road in the figurative sense is attested from 1894, originally political; edges of a dirt road can be washed out and thus are less safe, but the notion here probably is of the middle as "less exposed to ambush." Middle way in the figurative sense of "path of moderation" is from c. 1200. Middle ground as "place of moderation or compromise between extremes" is by 1961. Middle-sized "of medium size" is by 1620s.

In U.S. history, the Middle States (1784) were those between New England and the South (New York, New Jersey, Pennsylvania, Delaware). Middle America for "the 'silent majority,' the generally conservative middle regarded as a homogeneous group" is by 1968.

"a featherless plantigrade biped mammal of the genus Homo" [Century Dictionary], Old English man, mann "human being, person (male or female); brave man, hero;" also "servant, vassal, adult male considered as under the control of another person," from Proto-Germanic *mann- (source also of Old Saxon, Swedish, Dutch, Old High German man, Old Frisian mon, German Mann, Old Norse maðr, Danish mand, Gothic manna "man"), from PIE root *man- (1) "man." For the plural, see men.

Sometimes connected to root *men- (1) "to think," which would make the ground sense of man "one who has intelligence," but not all linguists accept this. Liberman, for instance, writes, "Most probably man 'human being' is a secularized divine name" from Mannus [Tacitus, "Germania," chap. 2], "believed to be the progenitor of the human race."

Specific sense of "adult male of the human race" (distinguished from a woman or boy) is by late Old English (c. 1000); Old English used wer and wif to distinguish the sexes, but wer began to disappear late 13c. and was replaced by man. Universal sense of the word remains in mankind and manslaughter. Similarly, Latin had homo "human being" and vir "adult male human being," but they merged in Vulgar Latin, with homo extended to both senses. A like evolution took place in Slavic languages, and in some of them the word has narrowed to mean "husband." PIE had two other "man" roots: *uiHro "freeman" (source of Sanskrit vira-, Lithuanian vyras, Latin vir, Old Irish fer, Gothic wair; see *wi-ro-) and *hner "man," a title more of honor than *uiHro (source of Sanskrit nar-, Armenian ayr, Welsh ner, Greek anēr; see *ner- (2)).

Man also was in Old English as an indefinite pronoun, "one, people, they." It was used generically for "the human race, mankind" by c. 1200. As a word of familiar address, originally often implying impatience, c.1400; hence probably its use as an interjection of surprise or emphasis, since Middle English but especially popular from early 20c.

As "a woman's lover," by mid-14c. As "adult male possessing manly qualities in an eminent degree," from 14c. Man's man, one whose qualities are appreciated by other men, is by 1873. Colloquial use of the Man for "the boss" is by 1918. To be man or mouse "be brave or be timid" is from 1540s. Meaning "piece with which a game (especially chess) is played" is from c. 1400.

Man-about-town "man of the leisure who frequents clubs, theaters, and other social resorts" is from 1734. Man of the world is from mid-14c. as "secular man, layman;" by early 15c. as "man experienced in the ways of the world, one able to take things in stride." To do something as one man "unanimously" is from late 14c.

So I am as he that seythe, 'Come hyddr John, my man.' [1473]

MANTRAP, a woman's commodity. [Grose, "Dictionary of the Vulgar Tongue," London, 1785]

At the kinges court, my brother, Ech man for himself. [Chaucer, "Knight's Tale," c. 1386]