It is impossible to say for sure without getting our hands on the software.
My guess from doing Point of Sale programming for many years:
Point of Sale software tends to be very configurable at the store. I suspect that this particular software doesn't have support for "special deals". That is, the software itself has no way to support things like "Buy a Mojito, get a free steak salad". The manager pokes around the software trying to figure out how to get this to work.
The software probably supports items with fixed prices and items with variable prices. Variable priced items ask for price. The manager things "aha! I'll make set up one of these for the steak salad and instruct my people to just enter zero!" He does so, capitalizing and indenting the "FREE STEAK SALAD" because he wants to highlight the special deal.
This works well enough. Cashiers sell mojitos, enter the "FREE STEAK SALAD" item number, then zero, then enter.
One day, a cashier isn't paying attention and forgets the price prompt. They are probably just typing blind from an order. They enter the "Free Steak Salad" item number than the "Angel Food Cake" item number. The latter is 1223. They look up, and the prompt says "FREE STEAK SALAD". "Huh", they say, at enter it again. It works, and they figure "must be a computer glitch" and stuff the receipt in the bill without looking at the price.
This may be exacerbated by the fact that older registers don't have CRTs but rather only a 2-line display. The display may not have the total price on it.
That's my guess. It's just a theory, though. There are many possible explanations. As others have said, it could also be that "FREE STEAK SALAD" is a fake item and the cashier got it by accident by mistyping the item number. I think that's less likely though.