There are two question.
First question: how to explain the change of meaning of the construction to play at the checker from chess ‒OED Checker 4]: obsolete ca. 1330‒ in draughts? There are two scenarios.
In the first scenario, the active role is for chess players: they were going to replace the construction to play at checkers by the construction to play at the chess. The word chess is the equivalent of French (jouer aux) eschecs. Eschec means chess piece. The construction to play at the checker was free then and could be used by draughts players.
There are three objections against this scenario.
First, a word, in this case checker, does not easily get quite a new sense, it is a rare phenomenon.
Secondly, the construction to play at the checker acquired another meaning just in the period draughts players started to play their game on the chess board. I know of course I should be prudent with causal connections, my head ache coming on has perhaps nothing to do with the shrieking gimlet of the electrician replacing wiring. All the same I bring it forward.
Thirdly, the 14th c. speaker does not change the meaning of the construction to play at the checker for fun, he should have had reason for it. But around 1300 English chess life seems to babble quietly on, from my 21st c. position I cannot find a reason for the change.
Therefore, the second scenario is preferable. In this scenario draughts players snapped up the construction to play at the checker, forcing chess players to invent another construction for the concept to play chess. And this implies that in medieval England draughts must have been far more popular than chess.
For the second question I look once more back on my study Dutch literature and linguistics. Teachers of the linguistic section payed attention to sociolinguistics, that is the school that tries to explain which social groups are responsible for changes in the language. Lydgate’s ye for example is in our days considered to be dated, but when, why and where did this process start? This school combines sociology with linguistic phenomena.
In chapter 3, I deliberately did not pose a sociological question. It would have been this one: in which French social group rose the game name dammes? From chapter 12 on I strike now and then upon the sociological domain, and that’s why I ask in this chapter 15 the same question for England: which social group was responsible for the changing meaning of the construction to play checker?
A tentative result of sociolinguistic research is, that in older days a language change started in a higher social class and slowly filtered through to lower classes. If in the case of the construction to play at the checker this higher class was nobility, in their castles and countryseats draughts has been far more popular then chess.
Apart from this supposition: when the social class of the wealthy citizens like draughts very much ‒see Lydgate’s text in 1426‒, I cannot find an argument why this is not true for nobility.
In this respect I refer to the miniaturist who around 1470 depicted the love couple Tristan and Iseult, king’s daughter, playing draughts. I hesitate if it is sensible to take the English writer who described about 1380 the most distinguished knights of their time playing draughts, chess and tables into account: literature is an unreliable source. On the other hand, the text does not follow the usual pattern of the romance of chivalry. This subject will be fully discussed later.
Tristan and Iseult playing draughts with chess pieces
My conclusion: in England, draughts was for more popular than chess, in all probability among noblemen and noblewomen also. This conclusion is totally inconsistent with the image I find in books and sites on board games. Who is wrong: the authors of these books and sites or the writer of this site? I chapter 15 I shall come back to this question.
The medieval European culture was international, naturally with regional differences. So, I am allowed to extrapolate: in France too, draughts was more popular than chess. The material in chapter 13 did not make this visible.