History may prove President Obama to be right or wrong about Obamacare, Cuba, and Iran, but it's important to note his courage in not just kicking the can down the road. One thing those three have in common is that we've been doing the same thing for decades and it clearly hasn't worked, and Obama is the president who decided to do something different. The latter two are not sexy legacy projects that a second-term president would naturally be drawn to. They're messy, decades-long impasses that too many politicians were content with just propagating to look tough.
Obamacare is not the liberal utopia of free universal health care, and neither the Cuban nor Iranian deals provide the satisfaction of total victory. Could he have been smarter or tougher or more cunning and gotten better results? Perhaps. But students of history should also remember that shortly behind the euphoria of defeating communism came the rise of international terrorism, not to mention the humiliation of Russia probably brought about Putin. Compromise may turn out to be the better part of valor.