If you see pressure as coming from the weight of the fluid above and now replace fluids with solids for a mental model, it obviously doesn’t work: imagine two parallel rigid plates connected by some rigid structure. The top plate will represent the (fluid) boundary between the top of the barrel and the tube and the bottom plate the bottom of the barrel. If you put a narrow column of metal on the top of the top plate, then the pressure exerted by the bottom plate is, say, p. If you make that column much wider, increasing the weight above, the pressure is say 10p.
I think the problem is that this intuitive model of pressure is just wrong but if it doesn’t come from the weight of the water above, it is hard to intuitively see where it does come from.