When President Obama was asked at a Thursday press conference whether he had confidence that Russia would hold to its end of that morning's agreement on ending the Ukraine crisis, was clear that he did not: "I don't think, given past performance, we can count on that."
Obama was also clear that, if and when the deal failed, he and European leaders would see that as Moscow's fault. And he was clear that Western leaders would respond with "consequences" for Russia. But he was exceedingly, worryingly vague on what those consequences would be and why they would succeed at pressuring Russia where past punishments had failed. And that's the whole dilemma right now: he knows what Russia is doing and wants to stop them, but it's just not clear if he has a plan for how.
It look fewer than 12 hours for Obama's pessimism on the deal to be vindicated: early on Friday, pro-Russia separatists in eastern Ukraine announced they would not recognize the agreement's mandate that they surrender the government buildings they'd occupied and declared to be an independent country. The separatists are widely thought to be backed by the Kremlin and to include unmarked Russian troops in their ranks.
Obama, in his Thursday comments, said that he was preparing for the deal to fail, and that he would see that as Russia's fault. "Russia's hand is in the disruption and chaos that we've been seeing in southern and eastern Ukraine," he said. "We're going to prepare additional responses should Russia fail to take a different course."
What does that mean? It does not mean a "military solution," which Obama ruled out. It does mean working with European leaders to "put in place additional consequences we can impose," but it's not clear who is on board and with what: Obama said only that he had spoken to German Chancellor Angela Merkel and that he was about to call UK Prime Minister David Cameron.
The greatest sign that Obama may not quite have a Plan B in place came when he turned to arguing that Russia's actions are self-isolating, are hurting the Russian economy, and that Russian President Vladimir Putin should realize that he's bringing himself more harm than benefit.
This is certainly true, but it does not lend great confidence in a looming American diplomatic counter-offensive because it: (1) frames this whole Ukraine mess as something that will sort itself out once Putin realizes that his actions are self-defeating; (2) seems to miss the fact that Putin already appears fully aware of what his Ukraine offensive is costing the Russian economy and seems to have calculated that it's worthwhile.
Obama can certainly threaten more of the targeted sanctions he and the European Union implemented last month. Those sanctions had some real force, targeting top Putin cronies and their preferred bank, but Putin does not seem deterred. Broader sanctions are certainly possible, but for them to be painful the European Union would have to buy in, and that would mean hurting Western European economies along with Russia's.
Western European countries, particularly Germany, have good historical reasons for being wary of Russian aggression in Europe and wanting to stop it. But those countries are also very tenuously recovering from the Euro crisis, and if you're a rationally self-interested Western European political leader you probably try to reflect the values of your voters, who presumably care a lot more about maintaining their own economy than about the sovereignty of eastern Ukraine.
That's why, in a real sense, Putin is winning: he's able to endure more than the West is willing to throw at him. If Obama wants a Plan B that will actually change Putin's strategic calculus, that means increasing the willingness of Western European countries to endure the economic pain necessary to effectively sanction Russia gas, Russian banking, and/or Russian military imports.
For Putin to continue winning, he mostly just has to keep things on a status quo: the unrest in eastern Ukraine is clearly more than the Ukrainian government can handle, which means it may be forced to accept Moscow's demands soon enough. For Obama to turn this against Putin, he'll have to change something pretty radical, most likely by convincing Western European leaders to sacrifice their own economic self-interest in defense of Ukrainian sovereignty. That's not an easy sell.