Yeah.

I mean, why pay the money? Why not just skip the payment and email a contact "1,000"? Or perhaps "Interesting article about in the Times about the USA, wink wink"?

This method is deliberately communicating information in a way that (I assume) is prohibited. It doesn't seem like it would take a judge much time to come to the conclusion that the gag order prohibits communication.

Creating a secret code is still communication, whether that's converting letters A=1, B=2, sending a video of someone communicating it in sign language, a painting of the country, writing an ethereum contract, everyday sending a voicemail with a list of all the countries in the world from A to Z, but omitting the one(s) that have the gag / warrant...