heel (n.) Look up heel at Dictionary.com
O.E. hela, from P.Gmc. *khangkh- (cf. O.N. hæll, O.Fris. hel, Du. hiel), related to O.E. hoh "hock." Heeled "provided with money" is 1880 in Amer.Eng., from earlier sense "furnished with a gun, armed" (1866), from still earlier sense "furnish (a gamecock) with a heel-like spur" (1562). To heel (of a dog) is from 1810. Heeler "unscrupulous political lackey" is U.S. slang, 1877, from the notion of one who follows at the heels of a political boss, no doubt coined with the image of a dog in mind. Achilles' heel "only vulnerable spot" is from 1810. Heel-tap was originally (1688) one of the bits of leather that are stacked up to make a shoe heel; meaning "bit of liquor left in a glass or bottle" first recorded 1688; the exact connection is uncertain. Down at heels (1732) refers to heels of boots or shoes worn down and the owner too poor to replace them.
heel (v.) Look up heel at Dictionary.com
of a ship, O.E. hyldan "incline," from P.Gmc. *khelthijanan (cf. M.Du. helden "to lean," O.N. hallr "inclined," Ger. halde "slope, declivity"). Re-spelled 16c. from M.E. hield, probably by misinterpretation of -d as a pt. suffix.
heel (n.) Look up heel at Dictionary.com
"contemptible person," 1914 in U.S. underworld slang, originally "incompetent or worthless criminal," probably from a sense of "person in the lowest position."