@cwebber https://www.goodreads.com/book/show/15784870-playing-at-the-world will probably answer this question in whatever level of detail you want. (I only took in the first hundred pages or so of detail)
@joeyh @cwebber
Dungeons & Dragons came out of the modding scene in this wargaming community, essentially -- as an offshoot of the already-marginal 'ancient battle wargaming' community.
The wargaming community was firmly on one side of the Two Cultures & didn't like the idea of fantasy or science fiction being mixed into their "historical re-creations", so D&D (with its emphasis on individual figures rather than whole squads) was marketed as its own thing.
@joeyh @cwebber
Since the tabletop wargaming community was heavily focused on reproductions of WWI and WWII, and depended upon fan newsletter style community building pioneered in the teens and 20s (wherein a community of amateurs would communicate via paid classified ads in the back of a semi-professional magazine), I suspect the community couldn't have been scaled up much earlier.
@joeyh @cwebber
It does. (In excruciating detail.)
The basic answer is:
Tabletop wargaming existed for a hundred or two hundred years before it was first successfully commercialized in the 1950s. This commercialization lowered the emphasis on complex and expensive figurines in favor of standardized mass-produced cardboard landscapes & markers.
The use of cardboard created a wargame community that hadn't existed before when it was too expensive.