My comments on brinksmanship probably should have been followed by an anecdote.
An experienced trial lawyer heard a younger colleague claim, "I've never lost a trial."Being a good trial lawyer arguably makes it harder to try cases, because you're more likely to get acceptable offers of settlement before trial. The younger lawyer may well be winning some trials that less skilled lawyers would lose. If you expect to lose a trial, you should be prepared to settle. If your client prefers the bird in hand and instructs you to settle, you may end up settling a case that you would prefer to try. But whatever your skill level, there's that range of cases down the middle where things could arguably go either way - and where the client is looking to you to decide whether to settle. If you always settle those cases you will protect your perfect record, but you forego the opportunity to stretch your skills, and potentially get a more favorable verdict (or mid-trial settlement) for your client.
"You know what that means," the older lawyer asked.
"It means that you don't try enough cases.
President Obama is a skilled but cautious lawyer. If he switched careers to trial litigator, I would not be surprised to find that he had a perfect trial record and was winning some "unwinnable" cases. But it's fair to observe that he is exceptionally cautious. It's that caution that drives some of his fiercest critics on the left to frothy anger. They want him to take up their causes now, and fully apply his skills to getting the result they desire (which may in fact be a desirable result) now. But instead he's evaluating whether he can win, and whether he should be expending political capital on that battle. If he decides that the fight isn't worth the price, he's open to compromise or putting things off.
Obama's correct to limit the issues he tackles, to set priorities, and to avoid fights that will damage his ability to advance his agenda. That's good political sense. But I do get the sense that there are some issues where he could prevail if he were willing to push them, yet nonetheless chooses inaction. Yet at the same time I think he needs to trust his political instincts. Were he to tackle a thorny issue and have to be the one who blinks, right-wing and likely also the mainstream media would happily drub him. For now I can see why that's a risk he chooses not to take.