Etymology
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loser (n.)
mid-14c., "a destroyer" (a sense now obsolete), agent noun from lose (v.). Sense of "one who suffers loss" is from 1540s; meaning "horse that loses a race" is from 1902; "convicted criminal" is from 1912; "hapless person, one who habitually fails to win" is by 1955 in U.S. student slang. Bad loser (also poor, sore, etc.) "one who takes defeat with bad grace" is by 1892.
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schlep (n.)
"stupid person, loser," 1939, short for schlepper "person of little worth" (1934), in Yiddish, "fool, beggar, scrounger," from schlep (v.) "to carry or drag" (for sense evolution, compare drag (n.) "annoying dull person").
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born (adj.)
Old English boren, alternative past participle of beran (see bear (v.)). "In modern use the connexion with bear is no longer felt; the phrase to be born has become virtually an intr. verb" [OED]. Distinction between born and borne (q.v.) is 17c. From early 14c. as "possessing from birth the character or quality described" (born poet, born loser, etc.). From 1710 as "innate, inherited;" colloquial expression in (one's) born days "in (one's) lifetime" is by 1742.
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schlemazel (n.)

also schlimazel, "born loser," 1948, from Yiddish shlim mazel "rotten luck," from Middle High German slim "crooked" + Hebrew mazzal "luck." British slang shemozzle "an unhappy plight" (1889) is probably from the same source.

A shlemiel is the fellow who climbs to the top of a ladder with a bucket of paint and then drops it. A shimazl is the fellow on whose head the bucket falls. [Rep. Stephen J. Solarz (D.-N.Y.), 1986]
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lemon (n.2)
"worthless thing, disappointment, booby prize," 1909, American English slang; from lemon (n.1), perhaps via a criminal slang sense of "a person who is a loser, a simpleton," perhaps an image of someone a sharper can "suck the juice out of." A pool hall hustle was called a lemon game (1908); while to hand someone a lemon was British slang (1906) for "to pass off a sub-standard article as a good one." Or it simply may be a metaphor for something which leaves a bad taste in one's mouth. Specific sense of "second-hand car in poor condition" is by 1931.
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technical (adj.)

1610s, "skilled in a particular art or subject," formed in English from technic + -al (1), or in part from Greek tekhnikos "of art; systematic," in reference to persons "skillful, artistic," from tekhnē "art, skill, craft" (see techno-).

The sense narrowed to "having to do with the mechanical arts" (1727). Basketball technical foul (one which does not involve contact between opponents) is recorded from 1934. Boxing technical knock-out (one in which the loser is not knocked out) is recorded from 1921; abbreviation TKO is from 1940s. Technical difficulty is from 1805.

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able (adj.)

"having sufficient power or means," early 14c., from Old French (h)able "capable; fitting, suitable; agile, nimble" (14c.), from Latin habilem, habilis "easily handled, apt," verbal adjective from habere "to hold" (from PIE root *ghabh- "to give or receive").

"Easy to be held," hence "fit for a purpose." The silent h- was dropped in English and resisted academic attempts to restore it 16c.-17c. (see H), but some derivatives (such as habiliment, habilitate) acquired it via French. Able seaman, one able to do any sort of work required on a ship, may be the origin of this:

Able-whackets - A popular sea-game with cards, in which the loser is beaten over the palms of the hands with a handkerchief tightly twisted like a rope. Very popular with horny-fisted sailors. [Smyth, "Sailor's Word-Book," 1867]
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booby (n.)

"stupid person," 1590s, from Spanish bobo "stupid person," also used of various ungainly seabirds, probably from Latin balbus "stammering," from an imitative root (see barbarian).

Specific sense "dunce in a school class" is by 1825. Booby prize "object of little value given to the loser of a game," is by 1884:

At the end of every session the dominie had the satirical custom of presenting his tawse [a corporal punishment implement used for educational discipline] as a "booby-prize" to some idle or stupid lout whom he picked out as meriting this distinction so that next time they met he might start fresh and fair with new pair for a new set of classes. [Ascott R. Hope, "Dumps," Young England magazine, Sept. 1884]

Booby trap is by 1850, originally a schoolboy prank; the more lethal sense developed during World War I. Booby-hatch "wooden framework used to cover the after-hatch on merchant vessels" is from 1840; as "insane asylum" by 1936.

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