What's more, in the case of Syria, one thing that we do know is that while Syria is an important ally of Iran's, the Iranians are simultaneously highly disdainful (and even contemptuous) of Syria—indeed, of all the Arab states. They believe that Iran is far more powerful and far more important than Syria. With that in mind, they could probably rationalize drawing virtually any "lesson" they wanted to from America's failure to act in Syria—or from an American attack, had we gone through with it. Some Iranians would no doubt have argued that 'while the Americans might be willing to hit the weak and unimportant Syrians, they would never do the same to Iran’, while others might contend that, 'the Americans had no need to strike Syria because it is small and unimportant and cannot threaten their interests; but Iran is so much more important and powerful that the Americans would never let us do the same.'
Again, when we finally learned about how the Iranians saw a particular event, we have so consistently been surprised, even shocked by their reactions that we need to be really careful about assuming that we know how they will react. Indeed, typically, different Iranian groups have their preferred policies and—like their American counterparts—simply rationalize whatever happens as further supporting their pre-existing position. So we need to make decisions about Syria based on what is in our best interests in Syria, and not how the Iranians see things. If we let that become the lodestar of our decision-making, we are going to end up chasing them down the rabbit hole.
AF: You recently stated that if America is “willing to actually build a better [Syrian] opposition, one without al Qaeda, it is not impossible to do so.” We saw reports in late September indicating that a number of powerful Syrian rebel factions have broken with the U.S.-backed Syrian National Coalition to create a new Islamist alliance that includes the Al Qaeda-linked al Nusra Front, thereby further marginalizing the more moderate Free Syrian Army. Given this, and the fact that extremist factions are proving to be the most effective fighters against the Assad regime, is America’s ability to build a militarily effective moderate opposition declining, or have the scales perhaps already tipped too far in the extremists’ favor?
KP: This is another huge question—one that needs an article to fully discuss. The short version is that it would have been much, much easier to build a better Syrian opposition if we had started earlier, but it is literally never too late. It is simply that the longer you wait, the longer it takes—although even then there is no reason that it could not be done in a 2-4 year time frame. (And it is worth keeping in mind that American elites routinely underestimate the amount of time that the US can remain committed to a policy if the White House favors it. From Bosnia to Afghanistan to Iraq, pundits have asserted that the US would not have the time to make a policy work, and in every case we did. I can remember being told repeatedly in early-2005 that the US could not spend 2-3 years to make a counterinsurgency/low-intensity conflict strategy work in Iraq, and yet 2-3 years later the Bush administration finally turned to it, and made it work in under 3 years.)
To stick with the Iraq example, as a result of the astonishing cavalcade of appalling mistakes made by the Bush administration in 2003-2006, the US had twice tried to build a new Iraqi military and failed miserably. We tried again starting in 2006-2007. The Iraqi army we started with at that time was completely overrun by militias, terrorists, criminals, and mendicants. Weapons provided to this army were routinely sold or given to militias, terrorist groups, and organized crime rings. Most leaders had been promoted for all of the wrong reasons, and the Iraqi people were terrified of it since it was so thoroughly infiltrated by death squads, extortion rackets, ethnic cleansers, and worse.
And yet, by 2008, the Iraqi military had been wholly reformed. It was—temporarily, until the US allowed the Iraqi government to thoroughly politicize the ISF beginning in 2010—a professional and reasonably capable military. The bad guys had been driven out; the good guys were promoted; and most had learned to be good soldiers who were proud to be defending Iraq. Of course, its capabilities were limited, but in terms of its professionalism, adherence to the law, and usefulness as a force to wage the war and protect the Iraqi people, it had been completely transformed.
There is absolutely no reason that the same could not be done in Syria. BUT it will require a big effort—not necessarily 170,000 combat troops like in Iraq, but certainly thousands of advisors and trainers rebuilding an opposition from scratch (as we effectively did again in Iraq in 2006-2007) and then working with Syrian formations for months if not years. And unless or until we are willing to make at least that level of effort, nothing else we are going to do has a high probability of changing the situation on the battlefield; and until we do that, we have almost no prospect of bringing about a negotiated settlement—until one side wins or both sides beat themselves to a bloody pulp. And they are still a long way from the latter.