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...
If you ever dealt with the laws around exporting technology to specific jurisidictions, this would be like saying "We can convert the algorithm code to Python and THEN export it to North Korea!"
One of the earliest example would be "we can print PGP as a book and then..."
I think the point here is to ensure they are legally compelled to make the payment. They can't admit to the gag order, but the existence of the gag order compels them to pay the 1,000 shekels, does the gag order compel them to not pay what they owe??