I’m pretty confident that Hillary has made up her mind about Putin.
Back when she came into office as Secretary of State, she was the sponsor of Michael McFaul, who became the US ambassador to Russia. McFaul, in turn, was the architect of the so-called “reset” initiative for Russian-American relations.
This policy was either incredibly naive or incredibly cynical; hard to say which. The kindest interpretation is that it reflected a natural impulse by any newly elected White House, especially one without foreign policy chops, to try and start over in international affairs. Another excuse is that the Obama team were coming in on the heels of our country’s whole traumatic experience with neocon leadership. Of course the new administration was tempted to assume that problems with Russia may have been, just somehow, George W. Bush’s fault.
On the other hand, Putin was fresh from victory in a limited invasion of Russia’s helpless neighbor, the Republic of Georgia. Through the fog of Russian disinformation, the truth is that the 2008 war was a long-sought means of crippling and discrediting Georgia’s pro-US leader, Mikheil Saakashvili, an anti-corruption reformer who came to power after the so-called Rose Revolution of 2003. Saakashvili had made the mistake of limiting certain Russian “business” interests in his country and flirting (modestly) with NATO membership. Worse yet, he was hugely popular in Georgia and beyond, living proof that a Putin-style mafia state was by no means the only post-Soviet option. Saakashvili’s success in reforming the notorious Georgian police forces, for instance, was just the sort of thing Putin didn’t want his own citizens to contemplate. In any case, the Russians crushed all opposition and easily occupied two big swathes of Georgian territory; and as of early 2009 they showed no intention of ever leaving again (and they are still there). But, as the new US policymakers argued, Saakashvili had his flaws too. Apparently he had even given the first order to fire in that very brief and one-sided conflict, like the bullied little kid who finally hauls off and punches Brutal Dufus in the nose.
All that was really needed now, according to the McFaul/Clinton contingent, was a fresh start, a lot of fanfare, a willingness to let bygones be bygones, and some enthusiasm for promoting bilateral business ties.
Whether or not McFaul and Hillary knew better, in my opinion they should have. There are people in DC who know Russia well. In addition, if you look at some of the Cablegate documents, you can see that the State Department was getting unvarnished information, all of which was ignored either out of rosy-eyed misconception at the top or for political expediency.
It wasn’t long before the Russian state media began playing up poor McFaul as a particular enemy and scapegoat. It began when he went so far as actually having a meeting with some of the Russian opposition (a normal practice for many previous ambassadors), and this of course became proof that he was masterminding the downfall of the regime. Then Putin had a bit of a scare at the popular outcry over falsification of the 2011 elections. While promising a few temporary reforms, the regime acted to put down all domestic opposition with brutal force. The US still had only the mildest protest against any of this, but soon enough there was the occupation of Crimea and the dirty war against Ukraine, plus the occasional armed flyover of NATO space or naval challenge on the high seas or media reminder of Russian nuclear arms capability; all on top of an unprecedented campaign of physical harassment of McFaul and the embassy staff, and of course the unrelenting hatred spewed at America in all the official media on a 24/7 basis.
So, let’s put it this way, the “reset” of the relationship didn’t work out very well. Today, McFaul likes to write about how awful Putin is and how sad the undermining of democracy in Russia has been. Hillary, too, stands in retrospect as a staunch opponent of Putin’s tyranny and international aggression. As a practitioner of Realpolitik, she will presumably still try to find ways to work with Putin on the international stage, but I’m pretty sure she has learned her lesson about who he is.