Let's consider for example the von Neumann ordinal numbers..
For finite numbers, it's obvious that there is no infinite descending chain. However what about the first infinite number $\omega$? Well, it contains all finite numbers, and exactly those. Therefore no matter which number you choose, from that point on you can only "descend" a finite number of times. And since you've done only one additional step, the whole chain will be finite as well (because a finite number plus one is still a finite number). That is, the length of your chain is always finite, but you can choose an arbitrary long finite chain.
OK, but $\omega$ is special, so what about $\omega+1$? Well, that differs from $\omega$ only by the extra element $\omega$. So you have two options: Either you select a finite number, then you obviously are in the exact same situation as before. Or you select $\omega$, but for $\omega$ we already know that all chains are finite, and you got just one more. Same argument goes for $\omega+2$ etc. And for $\omega\cdot 2$, we essentially get back to the argument we used for $\omega$.
Indeed, you can make this more general: For any ordinal, no matter which element (that is, which smaller ordinal) you choose first, the length of your chain will always be one more than the length you choose from the chosen ordinal. Therefore if all ordinals below $\alpha$ only admit finitely descending chains, then $\alpha$ does, too, because you need to select one element, and then you've already arrived at a smaller ordinal, so any chain from there is finite, and so the total chain, being one longer, is finite as well.
And indeed, the same argument can be made for the von Neumann hierarchy: Every set has a rank given by an ordinal, and each set only contains sets of lower rank. And thus the very argument I've given above for the ordinals works here, too.
Now what about sets not in the von Neumann hierarchy? Well, it turns out that ZFC doesn't have such sets. All ZFC sets are in the von Neumann hierarchy. And the reason for that is exactly the axiom of foundation.
Basically large sets are large because they have many elements, and therefore also many chains, not because they have long chains. The length of each chain is finite. The number of chains can be arbitrarily large.