Q From Virginia N Beach: I have heard the expression checkered past used for many years. What is the origin of it?
A Somebody with a chequered past, which is the British spelling I naturally use as opposed to your American one, has had periods of fluctuating fortune, though the focus is often on some past spell of reprehensible conduct. For example, The Times wrote on 6 June 2008: “He joined the church as a fully ordained Baptist minister in 1996 after a chequered past as a gambler.”
If the game of chess comes to mind, that’s a good guess, although it’s not the twists of fate experienced by the players that are meant, but the board that it’s played on. If American, you may also (or instead) be thinking of the game of checkers, played on the same board, which British players know as draughts (whose name, by the way, is from the obsolete draught in the sense of a move in a game).
Something chequered is marked like a chess board, with a geometric pattern of squares in alternating colours. It’s pretty much the same word as checked, both of which appeared in English in the fifteenth century. The latter was frequently spelled chequed in Britain until about a century ago but has now settled down to the ck spelling everywhere. Chequered in the literal sense is less common than it once was, although the chequered flag that’s waved when a racing car passes the winning post is well known.
That usage links us directly with its origin. Chequered came out of heraldry: the first known example is in the Book of St Albans in 1486. That said — in modern language — that heraldic arms are said to be chequered when they are made in two colours in the manner of a chess board. The word came from French escheker, derived from late Latin scaccarium, a chess board. Our exchequer is from the same source and originally also meant a chess board, though it came to be connected with finance through a table covered with a cloth divided into squares on which the accounts of the revenue were kept by means of counters.
The figurative idea behind chequered is of alternations of good and bad, like the colours of the squares on the board. As well as a chequered past, you can talk about a chequered history or a chequered career.