If they had sold some items for Eth just before the fork, they will never recover the Eth, and they may be unable to recover the items either. So yes, in a fork people lose money.
So if the forked chain becomes accepted, then they have 1000 USD and 1 Eth, while you have 0 dollars and 0 Eth, and you're never going to make the mistake of trusting a cryptocurrency ever again.