win (n.): Old English winn, "labor, toil; strife, conflict; profit, gain," from the source of win (v.). Modern sense of "a victory in a game or contest" is first attested 1862, from the verb.
win (v.): "be victorious," c. 1300 fusion of Old English winnan, "to labor, toil, struggle for, work at, strive, fight," and gewinnan, "to gain or succeed by struggling, conquer, obtain," both from Proto-Germanic *winn(w)an, "to seek to gain" (source also of Old Saxon winnan, Old Norse vinna, Old Frisian winna, Dutch winnen, "to gain, win," Danish vinde, "to win," Old High German winnan, "to strive, struggle, fight," German gewinnen, "to gain, win," Gothic gawinnen, "to suffer, toil"), from root *wen-, "to desire, strive for."
It is not surprising that a writer becomes frustrated at people not being able to understand words. Consider the oft-touted phrase, "There is no winning at D&D," which I hear all the time from particularly daft people who feel that it's necessary to define every activity by virtue of whether or not it can be won.
Somehow, this lack of winning seems a damning sort of condemnation ... until it is recognized that many enjoyable activities, such as swimming, laying in the sun, engaging in conversation and reading aren't defined by "winning" or "losing" either. This does not seem to hurt the popularity of these activities. I can't see how it matters, then, whether there is winning or not; but as I've put up the etymology of the word, we might just as well talk about it.
I love that "winning" is more traditionally associated with striving than with overcoming. I love, too, that gain and fighting are central to the meaning, more so than our modern take that the winner is the only person (or team) that counts. All sides struggle; all sides fight; and most of the time, the only real meaning to "win" with most games is to describe who happens to be in front when an arbitrary time limit is reached. If the last Superbowl had been permitted to go on twice as long, are we absolutely certain the Falcons would not have won? And if they had not, would that make it certain that they would not win if the game went on three times as long or four times as long?
Of course not. "Winning" is an arbitrary measure. When we say someone has "won" at Monopoly, are we describing the person or the dice roll? We are perhaps closer when we say someone has won at Chess, Checkers or Go; these are elimination games that are questions of pure skill; but does winning a game ensure that the player will win the next game? Or the next? If not, what does "winning" really describe?
I am happy that my favorite game ~ the only game I am interested in playing at this point ~ is not about elimination of players but about struggling, fighting and gaining. D&D is about accumulation, in a milieu where the accumulation can go on and on, without finish. Of course, a DM can mistakenly rush the accumulation process by pouring too much into the coffers of the players too quickly, which often happens. All too soon, players without any real skill or knowledge at playing the game are empowered with ridiculous advantages that quickly destroy game-play, mostly brought about by DM's who ignorantly assume that Chess could be a better game if one of the players was allowed to replace both bishops and both rooks with four queens. Quickly the benefits of too much accumulation destroys any hope of learning the fundamentals of the game, ensuring that thousands of tables never gain a modicum of skill. There's no need to understand how the knight works if both knights are flanked by queens.
For how else can one describe a proliferation of magic wands, rings, potions, smashing weapons and defensive armor that accumulates for most parties after only a few months of running? Where is the need to be careful or clever when fifty sorts of healing are available, floated by fifty sorts of bonuses when a hand takes the weapon? In such circumstances, for so many players, of course D&D isn't a game. It is hardly a past-time.
It is all too easy to rush and condemn all accumulation in this; to say that we should eliminate magical items altogether, along with levels, special attacks, excessive hit points, whatever might be called into the mix. But there is nothing wrong with a player climbing a level; if it is not the second time in a three-hour running. There is nothing wrong with a player gaining a magical item, if it is not a magnificent staff being given to a low-level mage. There is nothing wrong with a potion or two; but ten or twenty is surely overdoing it. There is nothing wrong with accumulation ... so long as it isn't a dump truck backed up and emptied into the campaign.
What we are asking for is a struggle ~ a grappling, grueling, uncertain contest where the common condition of overcoming an opponent is replaced with periods of lull and extreme terror, waxing and waning with irregular momentum. The gains from that struggle need only be sufficient enough to encourage further struggle; gains should never challenge the needfulness of the struggle's presence.
Yes, the players won't understand this. Players often misunderstand what is good for them; like little children left alone with a crockery jar full of brownies, they will glom onto them voraciously and devour them at once, until they grow sick and potentially hateful of ever eating brownies again. But if we will keep the jar out of the child's hands, and doll out a brownie now and then, the child's appetite for brownies will only increase, as they fantasize about the day they will have full access to the source.
Which we must never let them have. This is a central condition of being a good DM; the understanding that what players think they want is not what players want. On the surface, it seems cold, heartless, mean ~ just what we thought of our mothers when they would let us have "only one."
That was love. Some children never grow up enough to recognize that. But if we want to be grown up enough to be DMs, we have to learn what love means.