Vladimir Putin was still fairly new at the job of Russian premier and when George W. Bush said that he felt that he could "trust" Putin, it brought down a firestorm from the Western intelligentsia. Rather than seeing a Bush-Putin accord as an overwhelming force, the critics saw a potential detente as a sign of Bush's stupidity in the face of Putin's cold calculation. Whether Bush actually took this criticism to heart is debatable (though I believe he probably he did) because USA's response to 9/11 was a unilateral move that shrugged off traditional American allies and enemies in a desire to go it alone. I don't think this was a response to Putin, rather I'd say it was triggered by France (in the Security Council) and Germany (in NATO) instead. I think Bush saw unilateralism as a preferred option anyway, as going in with UN and/or NATO approval would've limited USA's military capabilities, would've put Syria (a Security Council member at the time) in the chain of command, would've put Turkey and the Iraqi Kurds at odds, and might've sparked a militaristic movement in Germany, which would only have complicated the task of tracking down al-Qaeda. Meanwhile, Putin fought Islamic terrorists on his own instead of in concert with the Americans.
The way Bush backed away from a potential Russian alliance was indicative of the general American opinion of Putin. Presidents are American political animals that aren't terribly close to foreign leaders so they are reliant on military and intelligence advisers to shape their perceptions (and/or their rhetoric). The Pentagon's initial perception would've been that Putin was the iron fist behind the velvet glove of Yeltsin, that Putin was a return to the norm of Russian dictators after a brief period of Gorbachev and Yeltsin. That Putin is nothing but trouble has remained the American attitude for the last 20 years. Bill Clinton had no interest in dealing with Putin, George Bush had a moment of wanting to make Putin an ally but that passed quickly, and Obama was resolved to keep Putin at arm's length (*) for his entire tenure in office. And that's just the Oval Office response. Think of all the high level advisers during that time who saw Putin as the #1 threat to American interests in the world: Madeline Albright, William Cohen, Condi Rice, Colin Powell, Admiral Mullen, Robert Gates, General Shalikashvili, Hillary Clinton, Joe Biden, and John Kerry, and I think we can comfortably add General Mattis, Mike Pompeo and John Bolton to that list, as well.
I listened to two Russian author interviews recently that left me with a coupla details about Putin that have stayed with me: 1) when Boris Yeltsin was grooming Putin to succeed him back in the 1990s, Putin actually wanted to be made the CEO of Gazprom instead; Yeltsin refused to hear it but Putin didn't really want to be the leader of Russia; 2) all Putin has ever wanted to is to be down with the President of the United States; he thought he had that with Bush after 9/11 but that honeymoon never really got started before Bush was done with him (and virtually all other foreign leaders). I bring these details up because Donald Trump represents a clear difference from previous administrations. And though Trump is surrounded by Generals, he is clearly a guy that shrugs off advice when it suits him.
Russia is naturally isolated. The terrain and the climate are harsh and the population is self-reliant and hearty. Diplomatically they continue to get even more isolated to the point where to me the danger is that Russia descends into a North Korea-like state where weapons and tough talk are their only exports. The difference is that Russia is a mighty nation that already has a nuclear arsenal--and knows what to do with it! And a population of 150 million people that have lurched toward becoming a productive middle class since the fall of the Berlin Wall. Ehhh....okay....not sure Russia has really embraced the potential of free markets to give people opportunities free from gov't interference but a steady diet of embargoes and sanctions isn't helping the Russian economy. Yeah, the society is still riven by inequality, the electoral process is clearly a joke and there is only the slightest burgeoning of a free media, but it feels like more people have more control over their time and money than in the Soviet days. Russia could've collapsed into pure chaos and instead has soldiered along fairly well considering the West hasn't been any more helpful than any other time in history.
I've always kinda liked Putin because I think he's tried to navigate through the post-Soviet economy in a manner that allows a middle class to develop, that allows people to get educated and make the most of their economic opportunities. And if that strikes you as a rosy-glass observation, take a look back at Russia's history--there are no Abe Lincolns, no George Washingtons, not a single Gandhi in 1000 years of history! Russians have had a steady diet of iron-fisted tyrants and Putin strikes me as the most progressive leader they've ever had. Putin has a firm grip on his domestic constituency (as shown by his recent "landslide" re-election) but in terms of foreign policy he's at the mercy of global markets that are mostly unavailable to him or simply not in his favor.
The recent National Defense Strategy paper that signaled a move away from international terrorism and back to a focus on great powers (meaning Russia and China), takes us back to a potential alliance--in the long run. Making enemies is, for USA, the first step to making friends. When we fight an enemy, we beat the enemy, then we re-build a friend (***). That's the American way. But in this case we don't have to make war with Russia. Russia is in desperate need of friends, all we have to do is ally with them.
The idea that the West can bully Russia into belching up another Yeltsin seems foolhardy at best. Putin's guaranteed to last another five years and though there is talk of his potential retirement, if he feels Russia is under attack, he'll stick around. Or worse: he'll be replaced by Putin 2.0.
Mikhail Gorbachev ain't walking through that door, folks. If we keep pushing Russia we may just push them into full fledged paranoid nihilism. Are we ready to topple all of civilization over some fucking Facebook ads? Putin still craves respect from the West. And the potential for war is all he's got left. It's going to get worse before it gets better--and I think it will get better. But not any time soon.
(*) During the 2008 election I thought the only clear advantage McCain had over Obama was Putin. I thought Obama was too green and Putin might eat him alive. I think Obama had a similar feeling and basically stayed away from Putin as much as possible for 8 years seeing him as nothing but a fox seeking a hen house.
(***) And the flip side: we never went to war with Brazil, for example, we've just subtly bullied them for 200 years so we don't see them now as an enemy or an ally. We see Africa as a charity rather than an investment because we've never feared it enough to make war with it or needed it enough to co-opt it. We still don't know what to do with Cuba because, outside of two weeks in 1962, we've never thought about besting it and thus don't know how to be friends or enemies now. Our wars shape our peace.