President Obama's hair-splitting on Syria is so clever that the war has been botched before it's begun. WRM has the timeline of the debacle, but he leaves out the complete failure to secure buy-in from the United Kingdom, our number one ally.
During his time in the White House, President Obama has repeatedly demonstrated a style of decision making that gets him in trouble. Especially when the stakes are high and the issue is complex, the President overthinks himself and tries to split the difference between tough policy choices. He comes up with stratagems that work beautifully on paper and offer well reasoned, moderate alternatives to stark choices. Unfortunately, they usually don't work all that well in the real world, with the President repeatedly ending up in the "sour spot" where his careful approaches don't get him where he needs to go.
This style of strategy is what's boxed him in and tied him in knots over Syria. He didn't want to intervene (too risky) but he didn't want to ignore the carnage completely (too heartless) so he split the difference and proclaimed a red line. He didn't lay the political preparations for war before the red line statement; again, too risky and too warlike. Instead, he split the difference once again: he made a threat without ensuring that he'd have the backing to carry it out.
Once the red line was indisputably crossed (after some more strategic hedging on his part when the red line was 'sort of ' crossed), President Obama then faced another decision: to bomb with or without Congress. Once again, intense reflection on his part led to split-the-middle decisions that made his life harder. He would bomb, but not bomb hard enough to make a real difference on the ground. That made his policies harder to defend for those who favored serious military action against Assad without doing much to build support from those who didn't want military action at all.
But even then the President wasn't finished splitting hairs. Bombing without Congress was too unilateral and too politically risky; but what would he do if Congress wouldn't sign a permission slip? It must have seemed like a brainwave in hair-splitting Cloudcuckooland: he announced first that he was definitely going to bomb, then that he was going to ask Congress before bombing, then that he wasn't necessarily bound by what Congress votes.