by a long chalk By a large amount, by a great degree, by far. This colloquial British expression derives from the practice of using chalk marks to keep score in various games. Thus, a “long chalk” would be a large number of marks or points—a high score. The equivalent American expression is by a long shot and both are frequently heard in the negative—not by a long chalk or shot.

by a long shot By a great deal, by far, by a considerable extent. This U.S. expression was in print as early as the 1870s.

A long shot is a contestant in any competition, most commonly athletic or political, with little chance of winning; therefore, with high odds in the betting. By extension, the phrase has come to refer to any bet or undertaking having little chance of success but great potential should the unexpected occur. Long shot connotes greatness of quantity or quality, if only in potential. Therefore, by a long shot means ‘by a large amount or degree,’ and the negative not by a long shot means ‘not at all,’ ‘in no way, shape or form,’ or ‘hopelessly out of the question.’

by a long sight By a considerable amount; a great deal; to a large extent. Sight in this expression may carry its meaning of ‘range or field of vision,’ and hence, indicate distance. By further extension, long sight in this Americanism refers to great quantity or degree rather than spatial distance. This expression dates from the early 19th century and is most frequently heard in the negative. Other variants are interchangeable with long, as in the following quotation from Mark Twain’s Huckleberry Finn:

by a nose By an extremely narrow margin, just barely, by a hair or whisker. The allusion is to a horse race in which the winner crosses the finish line only a nose ahead of his rival. This U.S. slang expression dates from the early part of the 20th century.

higher than Gilderoy’s kite Very high, higher than a kite, out of sight.

This chiefly U.S. expression is apparently a truncated version of hung higher than Gilderoy’s kite ‘to be punished more severely than the very worst of criminals.’ The allusion is to the hanging of the notorious Scottish highwayman, Patrick Macgregor, nicknamed Gilderoy, and five of his gang in Edinburgh in 1636. According to legal custom at the time, the greater the crime, the higher the gallows, and so it was with the gallows of Gilderoy that towered above those of his companions. As for the kite in the expression, two explanations have been offered. One is that Gilderoy was hung so high that he looked like a kite in the sky. The other, more scholarly, is based on the fact that kite or kyte meant ‘the stomach, the belly’ in Scottish and by extension was probably used to denote the whole body.

out of all scotch and notch Beyond all bounds or limits; incalculable, immeasurable, unlimited, unbounded. Rarely heard today, this expression is said to refer to the boundary lines, or scotches, and the corners, or notches, used in the children’s game of hopscotch.

room to swing a cat Plentiful space; ample room; a large area. This expression has several possible origins, none of them particularly plausible. One theory alludes to the sailors’ pastime of twirling a cat about by the tail, while another possibility refers to the former training exercise in which a cat was suspended in a bottle and shot at for target practice. Cat was also an old Scottish word for rogue; thus, the expression may have derived from the amount of room necessary to hang a wrongdoer. In any case, the phrase is often applied negatively to describe a lack of space or cramped quarters.