One of the critiques of President Obama that has some merit is that he is pretty risk-averse. He doesn’t take a lot of chances on things that might prove to be failures. For example, the President has been very clear about the fact that he would have preferred a single payer health insurance system. But he knew that the chances for failure with that were way too high (see: Vermont) and so he went for a more modest change to our current system with Obamacare.

The one time I can think of that the President took a big risk that didn’t pay off was when he attempted to negotiate a Grand Bargain with Speaker John Boehner. That one failed. But I also think that after all his talk of wanting to engage in bipartisan reform, he had to at least give it a go or prove himself to be yet another politician made of empty promises.

We got some idea about how President Obama evaluates risk on foreign policy from his interview with Tom Friedman.

He added that America, with its overwhelming power, needs to have the self-confidence to take some calculated risks to open important new possibilities — like trying to forge a diplomatic deal with Iran that, while permitting it to keep some of its nuclear infrastructure, forestalls its ability to build a nuclear bomb for at least a decade, if not longer.

“We are powerful enough to be able to test these propositions without putting ourselves at risk.

I suspect that Obama’s process of risk management is tied to his competitive desire to win. We’ve gotten a pretty big taste of that recently with the SCOTUS Obamacare decision and (even more so) with Congressional approval of TPA. The President tends to take risks when he has pretty well gamed out how to win. I’m reminded of this quote from Steven Waldman:

One can debate the extent to which these achievements happened because of Obama’s skills or his timing. I think his long view, maturity, and pitch-perfect sense of when to take the big risk (e.g., jamming through Obamacare after the Scott Brown election; invading Pakistan to kill Osama bin Laden) were major factors.

That “pitch-perfect sense of when to take the big risk” is the reason President Obama almost always wins when he engages on something 100%. His opponents would do well to remember that.

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