[meowface]

I suspect it's likely what he thinks it is: targeted harassment by someone he used to know or came in contact with in some way. This kind of thing happens a lot. I used to encounter this sort of thing myself, when some people online decided to try to harass me this way.

As long as there exist services that'll let you deliver something to someone by filling out a form online, with an option to request payment upon delivery, this kind of thing will always be possible.

Doing it for years does seem pretty crazy, though. If it is harassment, the harasser may be mentally ill.

[catalogia]

That doesn't explain why the pizza shops would continue to go along with this for years, not getting paid each time it happens. They would blacklist that address. Pizza shops blacklist addresses and phone numbers all the time.

Hell, I think half the reason this particular form of harassment is popular is because the target is often rendered unable to order pizza themselves, after getting blacklisted by every pizza shop in town.

[meowface]

It's unstated in the article, but it does say "orders of pizzas, kebabs, pittas and other food that he never ordered kept flowing in", which could mean it's a lot of different places delivering to him.

If the harasser is smart, they'd vary the restaurants and use a burst of different ones at a time in sequence, with long time gaps per restaurant.

And if the delivery driver isn't reporting it to the restaurants every time, the delivery person doesn't necessarily have a high chance of reporting it, so I see how it could continue for a while if there are a lot of restaurants in his delivery range. (Assuming it really is harassment, that is.)