I’ve been thinking about mass battles lately, and how the wilderness crawl was originally supposed to be a mass battle campaign. One only needs to look at the movement rates and encounter numbers to see clues for that. But the d20 combat system doesn’t support mass battles well.
And then I thought about how much actual combat sucks, especially for those low level characters between levels 1-3. Indeed, in D&D it feels like your individual character is just some nameless, highly disposable grunt in a dungeon. In fact it feels like if you want any success in a dungeon expedition, one must lead a whole platoon into it and only come out with the survivors.
And maybe that’s where a hidden genius of the design lies. Instead of playing as super capable heroes, you and your friends must take the role of disposable grunts and band together. Where in a wargame you would control a whole squad yourself, in D&D you just control an individual member of that squad. So you and your friends must coordinate and work as a team to survive. OSR is essentially a teamwork game.
Coming back to mass battles, maybe there’s another secret to the way wilderness works - by the time you’re wilderness adventuring, your characters should be at least level 4 - which in Chainmail terms is the level that they fight using the Hero rules. And Heroes and above can fight at the mass battle 1:20 scale. So maybe that tight knight squad you formed down in the dungeon is now wilderness adventuring, and each member of that squad now fights as 4 men. Suddenly their chances of survival are more favorable.
And of course, by the time one is ready to start campaigning in the world, he should be able to raise and equip an army of hirelings to fight for him as well.
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