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There are legitimate services commonly used to buy stuff from US sellers who don't want to deal with the complicated shipping to Russia and other countries. I doubt he had any intention to obscure his identity – the seller would just not sell to him directly.

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It's only legitimate so long as it isn't used to circumvent ITAR. The seller would probably not sell to him directly because exporting flight manuals for military aircraft was paper work the seller didn't want to deal with. By obscuring his identity through a third party the buyer violated ITAR, the seller probably also did as well by not doing proper due diligence.

Would that not make the middle man service guilty, not the buyer who probably has no idea about US law?

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