So, here's my take on an issue, in few coarse notes.
I've been thinking about skin-in-the-game as a justification for conscription/draft military service vs. voluntary/mercenary army.
I'll go there in a moment, but first an aside note. Sometimes it seems to me hearing Taleb striking some libertarian-ish notes. It's sort of a consequentialist libertarianism (arriving at libertarian attitude by evaluating the consequences of actions and policies, like the fragilising effects of centralisation and all that), which is different from categorical libertarians (starting from some fundamental moral prior, say the principle of self-possession, and constructing from there a libertarian theory, no matter the consequences). So it's kind of funny to see how skin-in-the-game may actually support something – conscription/draft military service – which sounds so un-libertarian.
But let me cut the crap, here's the argument.
Taleb's skin-in-the-game is a lot about getting right who is the agent and who bears the consequences of agent's actions. So how should we think about war and national defence? Who should be thought of as the agent, who ultimately goes to war, and who should be responsible for it?
I can't see any sensible answer other than ... the political/territorial community as a whole. This is even technically so: war and defence are ultimate public goods, it can't get more non-excludable and non-rivalrous than that.
So if community-as-a-whole is the agent, the skin-in-the-game principle would impose that it, as a whole, also bears the consequences. This logic to me makes incoherent the argument that there may still be allowed to transfer or trade risks (of dying or being wounded), like in the professional army or in a draft system with the possibility of hiring a substitute, as in the Union's draft system at a certain point during the American Civil War. It looks more coherent to me to frame the whole thing as a compulsory civil service for qualified individuals, similar to the jury system.
Let's look at the consequences. The point here is to see how the attitudes towards war of decision-makers would change, and more importantly, how the attitude of the public and the perception of the collective responsibility would change if we had a draft system instead of the current "voluntary" professionalised army. (This is possibly a big part of the explanation why there was such a greater public concern and outrage for the Vietnam war than for the wars the USA have been involved in in the last two decades).
At some point in his book "Antifragile", Taleb suggests that leaders deciding and handling the war should have their skin-in-the-game ("You want war? First in battle!", as was often the case in the past, from Alexander, Caesar, Hannibal to Napoleon roaming the battlefields). But the point of my communitarian twist of the skin-in-the-game principle is not so much that the POTUS and the congresspeople should have their skins in the game when dealing with war, but that in some way we all should.