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Let’s look at this theoretically.

(a) Putin while a mixed bag of good and bad could have good or bad motives for supporting any western leader or government. Indications of his support for Trump, in theory, would not be necessarily for bad reasons. He might just prefer Trump to HRC as a leader with whom he would need to do some face to face negotiation. There again, motives could be good or bad.

(b) Support for any particular candidate could be based on what Putin thought he could gain in Russia’s interest. Perhaps he might think Trump would be closer to his views on Syria, probably true given the record of DC globalist hawks. He might see Trump as more aligned with his views about national sovereignty, less concerned with Ukraine than the Democrats. Personally, I think Russia had some good reasons to want to retain influence in Crimea for their own national security. The other parts of their conflict with Ukraine are quite murky but essentially none of our vital concern so long as they remain isolated to Ukraine (if transferred to the Baltics or Poland, then more directly a concern to us).

(c) Putin may simply have despised HRC to the extent that any viable alternative would be preferable. I think that matched the mood of the electorate outside of the larger urban areas so one could say the mood of the electoral college (and thank God for its existence).

(d) one would need to consider bad reasons for support, as in having a malleable person in power — that might have explained the fairly warm relationship with Obama more than Trump. But if that’s what he expected, apparently it was a miscalculation anyway.

(e) could be a gender based thing, perhaps Vlad prefers to deal with men generally speaking. Merkel for example, quite cringe-worthy. HRC even more so.

The idea that a Russian leader will automatically want to create trouble in the U.S.A. and would prefer a weak leader there is classic cold war doctrine but Putin is a less predictable entity than a Brezhnev or Andropov. A stronger America means a weaker China. That could be the key to the whole thing. You could argue for a good version of Russian collusion, while America’s usual friends like Britain and Australia (and to some extent Canada although we tend to realize we are too close to be making trouble without trade consequences) appear to have become bad actors, like the French and Germans more typically have been, Russia and even North Korea are now good actors interested in a stronger America to reduce the influence of China. Hence also the very good relations between Trump and Japan’s leaders.

The idea that Russia will always be the geopolitical adversary of America is something worthy of challenge, if only because Mitt Romney is fixated on it, as was McCain and HRC etc, so whatever they believe, I want to think the opposite. Perhaps Russia has more overlapping interests with the U.S. in this modern world. There are old reflexes that don’t just easily turn off, Venezuela provides an example of that. But the path to success for American foreign policy vis a vis Russia is to look for obvious areas of mutual interest and exploit them. One could point to anti-terrorism, stable trading arrangements, keeping Chinese expansionism in check, space co-operation, and with Trump in power, anti-globalism (downplaying climate change hysteria for example).

So there’s lots of reasons why Putin might back Trump and not any Democrat. And it’s perfectly normal in geopolitics for that sort of thing, making it sound like a heinous crime of some kind is just the Democrats being childish because they weren’t picked.

I don’t believe in the alternate theory that Putin actually prefers the Democrats and did all these things just to sabotage Trump. I can’t see any good reason why Putin would want Democrats running America. While it would weaken America and he could think that’s a good thing, their way of weakening America might involve dangerous confrontations with Russia and its proxy Syria. So that’s not a good way to get to the desired result. And a weak America means a very strong China.