To calibrate our beliefs we need to figure out with what probability Putin thinks Obama has this view.
Yes, assuming it's one of the many issues Putin pays any attention to. What are the odds of Putin even considering the possibility that Obama might be a hidden left-wing anti-patriotic conspirator whose main agenda is to break the evil US empire? This is an easy question to answer. Presumably Putin is to the left of the "left-wing intellectuals" with his views on the evilness of the US empire, right? And actual US "anti-patriotic" left-wingers certainly don't consider Obama one of them, judging by the amount of criticism they fling at him. So Putin almost surely sees Obama as the current symbol of US imperialism trying to prevent Russia from exercising its rights to protect Russian citizens in formerly Russian territories. He may well think that he is weak and try to take advantage of it, but he certainly does not think that Obama is secretly anti-american, no more than he thinks that Obama is secretly Kenyan. My guess is that you think this is an option worth considering because of your own political views, which are obviously anti-Obama. This leads to a selection bias where you exaggerate the likelihood of negligible-probability alternatives related to the views you disagree with.
Obama clearly wants to pull the U.S. out of Iraq and Afghanistan, which under Bush were big parts of the U.S. empire. Lots of Republicans think that Obama wants to greatly reduce U.S. military power, so why is it silly to think that Putin might think that Obama wants to do so?
but he certainly does not think that Obama is secretly anti-american,
I take it you don't have much experience talking with leftwing college professors. It's far from implausible to think that deep down Obama believes that U.S. military power has, with the exception of WWII, been...
Some of the comments on the link by James_Miller exactly six months ago provided very specific estimates of how the events might turn out:
James_Miller:
Me:
"Russians intervening militarily" could be anything from posturing to weapon shipments to a surgical strike to a Czechoslovakia-style tank-roll or Afghanistan invasion. My guess that the odds of the latter is below 5%.
A bet between James_Miller and solipsist:
I will bet you $20 U.S. (mine) vs $100 (yours) that Russian tanks will be involved in combat in the Ukraine within 60 days. So in 60 days I will pay you $20 if I lose the bet, but you pay me $100 if I win.
While it is hard to do any meaningful calibration based on a single event, there must be lessons to learn from it. Given that Russian armored columns are said to capture key Ukrainian towns today, the first part of James_Miller's prediction has come true, even if it took 3 times longer than he estimated.
Note that even the most pessimistic person in that conversation (James) was probably too optimistic. My estimate of 5% appears way too low in retrospect, and I would probably bump it to 50% for a similar event in the future.
Now, given that the first prediction came true, how would one reevaluate the odds of the two further escalations he listed? I still feel that there is no way there will be a "conventional battle" between Russia and NATO, but having just been proven wrong makes me doubt my assumptions. If anything, maybe I should give more weight to what James_Miller (or at least Dan Carlin) has to say on the issue. And if I had any skin in the game, I would probably be even more cautious.