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If they are registering the name for the purpose of competition (or coercive cooperation) isn't it a slam-dunk infringement lawsuit?
Some lawyer, somewhere, is likely drawing up a class action suit. Relatively easy to identify and sign up clients.
"sometimes" from what I've heard elsewhere it should read "nearly all of the time, to benefit financially".
I have the impression that a class action "cost of doing business, and only if you get caught" handslap only emboldens others.

Would the following work to curtail practices like this?... Courts hit one so hard with punitive damages, and perhaps criminal investigation, that the company is wiped out. Then VCs decide it's bad business, and discourage practices like that (including by not funding someone who tries it once and expects to just serial entrepreneur if it fails), and then other companies take notice.

My father owned a small business that this happened to. Not Grubhub but a "yellow pages" type site set it up. The contact information was correct, so we didn't think much of it. The site went down after a short period, most likely whomever was funding it ran out of money. In his case it was a speculative sales tactic.
If a restaurant already has a contract with GrubHub and somewhere buried in the contract it gives GrubHub permission to do this... then it's still shady, but owners should also be reading their contracts closely -- and for owners who don't have a website at all, it could even be beneficial.

BUT... if GrubHub has done this (which they reportedly have, although they seem to be denying it) for businesses they haven't signed a contract with... then is that not highly illegal? There have to be laws against false representation in business, no? Whether cut-and-dried trademark infringement, or otherwise?

If that's the case, I hope they get a serious class-action suit against them with massive punitive damages. It's deeply unethical and anticompetitive, and basically smells of extortion.

If in 2019 you haven't bothered to buy the domain name for your restaurant you can't call this "cybersquatting", honestly.
They're setting up domain names similar to ones the restaurants already own (ie the restaurant owns .com, they buy .net and drive traffic to it)
How many domains should I be expected to buy? Give me a restaurant and I could probably come up with 100 reasonable sounding domains the could potentially be that restaurant.
> Grubhub registered 23,000 internet domains, many of them resembling the names of restaurants

Emphasis added.

Further, in The New Food Economy article [1]:

> Grubhub purchased three different domains containing versions of Shivane’s restaurant’s name—in 2012, 2013, and 2014.

[1] https://newfoodeconomy.org/grubhub-domain-purchases-thousand...