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I was quite surprised that nobody brought this up yet, but to me it is fairly clear that this is what Taleb's antifragility MUST look like upon close inspection: a lot of "free energy" trapped in such a way that only destructive shocks can release it. Any system that actually benefits from destructive shocks must look mad, consisting of crazy parts. If all the trillion-dollar-bills lying around were accessible (and hence immediately picked up) "in peace time", there would be no reserve for dealing with unexpected shocks from unknown unknowns well outside of the civilization's current model of reality.
The Visitor's civilization is fragile: there is no way a random destructive shock can improve on it, as if it could, they would have done that improvement already without the destructive shock. Destructive shocks can only harm it to various degrees. Whereas Earthlings might just stop the industrial-scale killing of babies (a huge win, obviously), if some important parts of our civilization get destroyed.
This sort of thing actually does happen. The reason North America currently uses 110-125V household AC is that when the standards were created about a century ago, the best insulators could safely insulate only for such voltages. Ever since North America is trapped in a Nash equilibrium wasting copper, electricity and occasionally burning homes and offices due to requiring twice the current for the same power compared to a 220-250V AC system. And do not forget the need for surge protectors or the destruction from not using them. I would not be surprised if this particular bill lying in the street (but glued there by a very stable Nash equilibrium with multiple moving parts) would be worth trillions of dollars, if all effects are added up. In Europe, people managed to pry it off the street, but only after huge parts of the electric infrastructure were bombed to dust or otherwise destroyed in WW2. At that point, it became possible to upgrade, making use of the opportunity afforded by better polymer insulators for wires.
I agree with Taleb that the ability to benefit from destructive shocks is key to long-term survival. But in order to achieve it in practice, the system needs to be stuck in a suboptimal state, with trapped free energy that can only be released upon a destructive shock and not accessible otherwise. The system does rely on these shocks coming from time to time, but they do. Sometimes it is the shockwaves from something snapping inside the system. For example, if the system wastes some non-renewable resource in a crazy Nash equilibrium, when that resource runs out, it may well provide the needed shock that would jolt it to a more efficient Nash equilibrium.