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"1000+ little Russian flags specially printed with “Trump” had to cost thousands of dollars, I would think. Some minor journalist was not going to fund this out of pocket, this was bought and paid for by one of the hateful leftist entities."

I've designed custom t-shirts through one of those on-line companies, and a single t-shirt can easily cost you $20 or more. Of course, the cost per item goes down with volume purchases, and I don't know what the cost of a small flag would be relative to the cost of a t-shirt.

But, at the very least, this would cost hundreds of dollars, and possibly - as you suggest - several thousand dollars, a pricey tab for a one-off prank. This suggests some sort of institutional funding, not one journalist paying out of his own pocket.