I also assumed randomness would balance things out, but "balance things out" means maximum entropy distribution.

With 100 people, there are only 100 configurations where one person has all of the money. But there is also only one single configuration where everyone has the same amount of money. There are a small number of configurations where everyone has almost the same amount of money.

The vast majority of the configuration space consists of configurations that on a macro level fall under the umbrella category "unequal". This is not because they are more likely states, but just because there are so many of the states we would label "unequal".