It’s never nice to be called a cheapskate, especially if it’s true and you really are a miserly or stingy person.
The second part has nothing whatever to do with any of the more common senses of skate. A writer in the San Francisco Chronicle in September 2007 was way wide of the mark when he wondered if a cheapskate was managing to avoid paying his share by adroitly sliding past the transaction, as though on skates or a skateboard. And there’s nothing in the least fishy about the word.
Well, up to a point. The origin, as often with slangy words, isn’t easy to fathom. Skate began to appear in print in the US at the end of the nineteenth century, almost simultaneously meaning a worn-out horse, a mean or contemptible person, and a second-rate sportsman (later, in the Royal Navy, according to Eric Partridge, it became a slang term for a troublesome rating). Cheap was added early on to refer to a person’s tight-fisted nature rather than any of his other perceived inadequacies. An early example appeared in the Newark Daily Advocate of Ohio in 1896 in a story about a streetcar motorman who was remonstrating with a driver of a coal wagon: “You’re a gol dinged, insignificant, pusillanimous, ragged, cheap skate of a tenth assistant barnyard corporal.”
The best suggestion we have is that skate was originally a Scots contemptuous word, still known in a weakened sense in Australia and New Zealand, where it’s usually written as skite. We retain it in blatherskite for a person who talks at great length without making much sense. It appeared first in a slightly different form in a Scots song, Maggie Lauder, written by Francis Semphill about 1643 (“Jog on your gait, ye bletherskate / My name is Maggie Lauder!”). This was a camp song among American soldiers during the War of Independence and remained popular in the decades that followed. We guess that this may have helped skate or skite to be preserved among emigrant Scots and others in the US during the nineteenth century.
By the way, the fish sense of skate is from Old Norse skata; the word for ice skates and similar devices come to us from Dutch schaats, although its origin is the Old French escache, meaning a stilt; there’s also the South African sense of a disreputable or irresponsible young white man, which may be from Afrikaans skuit, excreta.