Entries linking to freeman
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.
"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 class 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.' 
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]