I think it is a little unfair to blame this totally on Obama, although clearly the Russians see him as the return of Jimmy Carter. The Bush administration made it a point to lord it over the Russians that we won the Cold War and they lost. We tried to expand NATO right up to their doorstep, which means we were extending a treaty obligation to go to war to protect former Soviet satellite states if they got into a Georgia-type dispute with Russia.
You have to ask if that made any sense. Clearly it did to the neo-cons who ran foreign policy for Bush. They saw it as protecting newly democratic states and eliminating any zone of influence for Russia.
Russia saw it as overreaching. When they had a chance for some payback, they took it. They are running the iranian nuclear reactor program. They are pulling out all the stops to prevent construction of early warning radar in eastern europe. Now they are using cuba and venezuela to give us a taste of what it feels like to have a super power nosing around in your backyard.
They started this under Bush. According to an article in the Washington Post this morning, they made numerous bomber flights along the east coast and landed in cuba. Bush brushed it off as irrelevant, but I have to think that was a case of trying to make the best of a situation he couldn't do anything about.
We know how this plays out. First, planes are based in cuba, then venezuela. Next troops to protect the airfields. Then defensive antiaircraft missiles. Then short range, ground to ground and anti-ship missiles. Then medium range missiles that can target the US. Next nuclear missiles.
A weak Obama facing manifold problems both domestically and overseas will be in no position to do anything about it. He lacks the personal credibility to face down the russians, and he is broadly sympathetic to the leaders of cuba and venezuela, so he is not going to challenge them.
What could he do? As I see it, he has three options. One, reach a deal with Russia. They pull back and in return, we drop NATO expansion and early warning radars. They may not go for that however, since they have pretty much already achieved both goals.
Option two is to start serious harrassment of the flights. Bumping them, crowding them, subjecting them to heavy jamming, high power microwave radiation, etc. Eventually fire warning shots and maybe an "accidental" shootdown, like they shot down that KAL flight years ago. Chances a wimp like Obama will do this? Zero and they know it.
Option three. Put pressure on cuba and venezuela. Carrot and stick approach. Get rid of the russians and we lift trade embargo on cuba and expand ties with venezuela. Let them stay and we start financing internal opposition, expand embagoes, etc. Not a very credible option either, since Obama is already trying to offer them the carrot without getting anything in return.