https://www.brookings.edu/blog/order-from-chaos/2018/03/05/dont-rehabilitate-obama-on-russia/
..But not everything is relative; we should not slip into collective amnesia over the Obama administration’s weak and underwhelming response to Russian aggression. Throughout his presidency, Obama consistently underestimated the challenge posed by Putin’s regime. His foreign policy was firmly grounded in the premise that Russia was not a national security threat to the United States. In 2012, Obama disparaged Mitt Romney for exaggerating the Russian threat—“the 1980s are now calling to ask for their foreign policy back because the Cold War’s been over for 20 years,” Obama
quipped. This breezy attitude prevailed even as Russia annexed Crimea, invaded eastern Ukraine, intervened in Syria, and hacked the Clinton campaign and the DNC. Obama’s response during these critical moments was cautious at best, and deeply misguided at worst. Even the imposition of sanctions on Russia for its invasion of Ukraine was accompanied by so much propitiation and restraint elsewhere that it didn’t deter Russia from subsequent aggression, including the risky 2016 influence operation in the United States. Obama, confident that history was on America’s side, for the duration of his time in office underestimated the damaging impact Russia could achieve through asymmetric means.
Obama’s cautious Russia policy is grounded in three conceptual errors: a failure to grasp the true nature of the Russian threat, most clearly visible in his administration’s restrained response to Russia’s annexation of Crimea in 2014; a “long view” of historical trends which in his view inexorably “bent” toward liberalism; and the perception that formidable domestic political obstacles stood in his way when it came to crafting a response to Putin’s assault on the elections in 2016.
The Obama administration viewed Russia as a declining economy and, at best, a regional player and spoiler. According to a strict “spreadsheet” analysis of the situation, this was not a crazy read. Despite its sprawling geographic reach, Russia’s GDP is roughly that of Spain (about $1.2 trillion); it contributes less than 1.5 percent to global GDP, compared to the U.S.’ 25 percent. Without a jump in oil prices to shore up its petrostate model, Russia’s economic outlook looks grim. Furthermore, Russia’s population is literally disappearing: the country is facing major demographic challenges due to declining birth rates, low life expectancy (especially for men), and emigration. And while Russia is still a nuclear superpower, its military is no match for the United States and NATO. For all these reasons, the Obama administration concluded that, despite divergent views on international order, Moscow could still be a potential (junior) partner on areas of mutual interest. This set of beliefs proved incredibly sticky despite Russian actions that should have set off alarm bells.