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Yes, actually NYC (well, NY State Dept. of Economic Development) constantly goes after people for infringement of the "I heart NY" logo. They definitely do follow through.

It's not about money being made, it's a legal necessity that a trademark owner needs to actively defend the mark in order to keep it.

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Right, of course. I meant you could have a "J' (heart) Bruxelles" in the same design and not get sued, so long as Brussells hadn't had that TMed. At least I'd hope not.

You could probably expect to get a C&D letter from NY State for designing a logo like that. At least, plenty of other people have. Google for "i heart nyc trademark infringement" and read the top few links. Apparently they have sent out over 3000 such requests since registering the mark.

Sometimes the claims of infringement are upheld, sometimes not. The more important thing, legally, is that NY needs to show that they are actively defending the mark to prevent trademark dilution.

In order to keep it to what purpose? To make money.

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