Etymology
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Words related to Middlesex

Essex 
Old English East-Seaxe "East Saxons," who had a 7c. kingdom there. See east, Saxon.
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Wessex 
Anglo-Saxon kingdom in southern England, literally "(land of the) West Saxons;" see west + Saxon. Modern use in reference to southwestern England (excluding Cornwall) is from Hardy's novels.
middle (adj.)

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 class regarded as a homogeneous group" is by 1968.

Saxon (n.)

c. 1200, Sexun, Saxun, "member of a people or tribe formerly living in northern Germania who invaded and settled in Britain 5c.-6c.," from Late Latin Saxonem (nominative Saxo; also source of Old French saisoigne, French Saxon, Spanish Sajon, Italian Sassone), usually found in plural Saxones, probably from a West Germanic tribal name (represented by Old English Seaxe, Old High German Sahsun, German Sachse "Saxon").

This is traditionally regarded as meaning "warrior with knives" (compare Middle English sax, Old English seax, Old Frisian, Old Norse sax "knife, short sword, dagger," Old High German Saxnot, name of a war-god), from Proto-Germanic *sahsa- "knife," from PIE root *sek- "to cut." But Watkins considers this doubtful.

The word figures in the oft-told tale, related by Geoffrey of Monmouth, who got it from Nennius, of the treacherous slaughter by the Anglo-Saxons of their British hosts:

Accordingly they all met at the time and place appointed, and began to treat of peace; and when a fit opportunity offered for executing his villany, Hengist cried out, "Nemet oure Saxas," and the same instant seized Vortigern, and held him by his cloak. The Saxons, upon the signal given, drew their daggers, and falling upon the princes, who little suspected any such design, assassinated them to the number of four hundred and sixty barons and consuls ....

The OED editors helpfully point out that the murderous shout in correct Old English (with an uninflected plural) would be nimað eowre seax. For other Germanic national names that may have derived from characteristic tribal weapons, see Frank, Lombard. Celtic languages used their form of the word to mean "an Englishman, one of the English race" or English-speaking person in Celtic lands (for example Welsh Sais, plural Seison "an Englishman;" Seisoneg "English;" compare Sassenach).

As an adjective from late 14c. (earlier was Saxish, c. 1200); in reference to the later German state of Saxony (German Sachsen, French Saxe) in central Germany it is attested by mid-14c. Bede distinguished the Anglo-Saxons, who conquered much of southern Britain, from the Ealdesaxe "Old Saxons," who stayed in Germany.

Saxon is the source of the -sex in Essex, Sussex, etc. (compare Middlesex, from Old English Middel-Seaxe "Middle Saxons").