This is feeding somewhat off my Cosmopolitanism and Vietnam article. You may wish to give that a read.
Let me pose a question: how would one connect the small band of freelance adventurers, religious zealots, magicians, mystics and such as seen in many an RPG to a military organisation?
Well, there are a few simple answers. Mercenaries are nothing new - even if the dozen or so personnel that any given band of heroes could offer are hardly going to sway the fate of nations on the battle field. Irregular units are perhaps as old as regular units, or indeed older - it just needed a moment to identify them as formally irregular (if you will). The same might be said of guerrillas or partisans.
There are perhaps better solutions to this. But what I wish to talk about is something else. Jumping off that previous article, I happened upon a copy of Popski's Private Army in the library at home. For those who don't know, it is the history of a man, Vladimir Poniakoff, not a regular soldier, who effectively started his own special forces unit - the titular private army - in the British Army in the North African campaign of the Second World War.
Without diving too heavily into the details of the history of the unit, this appears to be the sort of time and place in which this little unit - less than thirty men under arms - could function and exist in connection with an organised, deeply formal organisation - that is to say, the British and Imperial forces. This is the same place the Long Range Desert Group came into being, and, indeed, the SAS. Numerous units from allied nations or resistance groups seem to have existed in the same sort of space.
Reflecting on this, my mind went gently to Evelyn Waugh's Sword of Honour trilogy of novels. These detail the experiences of Guy Crouchback, a British Catholic nobleman and his military service during the Second World War - or indeed, his lack thereof. Based on Waugh's own experiences as a man in his late thirties joining the army and on the whole, failing to find his place. Both Waugh and Crouchback end up in a Commando Unit and take part in a series of failed military operations.
The whole thing comes off as somewhat satirical of military life - the chivalrous Crouchback unable to come to grips with the enemy, sent to desk job after desk job-, even if the tragedy of the Second World War and Waugh's lament for the undoing of the old order stand out most prominently by the conclusion.
Both 'Popski' and Crouchback exist in a sort of space where a band of adventurers could link itself to a modern army; where the money would be flowing plentifully enough to be spent on such a group, and where the need would be felt most keenly for these rough-hewn mercenaries.
Incidentally, the regiment Guy Crouchback ends up in is the fictional Royal Corps of Halberdiers. I like to use this in the same context I might Ruritania or Barsetshire; a fiction with real roots. For the United States, I thought up the fictional state of West Dakota - a decent proportion of the European settlers of which might well have been Ruritanian refugees.