I vaguely remember that he went to Russia a few times in the 80’s. At the time it was seen as a failed attempt on his part to build a hotel. In retrospect, it looks like Russia was grooming him using free trips. Again, I just think he was too stupid to realize what was going on.
Keep in mind that there's a difference between an asset and an agent. He is definitely not smart enough to be a full-on Russian spy, but he's 100% dumb and corrupt enough to be manipulated/bribed into being their asset. Some assets don't even realize that's what they are, though I sense he knows.
This all makes sense with the Mishandling of top secret documents. Read an article in Foreign Affairs, I think that it was suspected that he was sharing information to Putin before, during and after his last term.
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Maybe he knows now, but I’m still not sure on that. That’s how stupid and self-unaware I think he is.