1. Bashar al-Assad has outmaneuvered President Obama. After the US threatened to bomb Assad in 2013, the Syrian leader allowed the Islamic State in Iraq and Syria (ISIS) to grow into such a serous threat that the US is now bombing it instead. But it's looking increasingly likely that the only way that he can stay true to the goals and priorities that have shaped his Syria policy since the war began in 2011 is by allying, either explicitly or tacitly, with Assad. That's not to argue that he should — this would only perpetuate Syria's long-term problems — but, unless something changes, that is the trajectory of American policy in Syria.
2. Everyone outside of the White House — and here I include not just analysts but members of the State Department, Pentagon, and intelligence agencies — agrees on one thing: President Obama's Syria strategy is a self-contradictory mess. The core problem is that Obama is committed to breaking ISIS' hold on Syria by bombing them from above while "moderate" Syrian rebels fight them on the ground, but he's doing it in a way that actually weakens those rebels, who were already too weak to beat ISIS.
3. The strategy is supposed to be reconciled by arming Syria's "moderate" rebels. But Obama's not willing to arm them enough to actually win. Even worse, his attacks on ISIS are undermining those rebels. They're freeing up Assad to focus even more on fighting the rebels, which is exactly the situation that Assad had hoped to engineer. So both Assad and the rebels are focusing more on fighting one another, and thus less on fighting ISIS.
4. Obama is not totally without reason here. The "moderate" Syrian rebels are intermixed with al-Qaeda's local wing, Jabhat al-Nusra, at such a granular level that it is impossible to help the moderate rebels without strengthening al-Qaeda. At the same time, Obama has repeatedly and correctly noted that Assad's brutality has helped give rise to ISIS. So Obama is stuck intervening in a three-way war in which he opposes all three sides.
5. Obama's Syria strategy in many ways encapsulates his greatest strengths and weaknesses as a foreign policy president. It is restrained, cautious, and appropriately modest. It is also palpably indecisive, almost a cliche of Solomonic splitting-the-baby, in which Obama commits fully neither to backing Syrian rebels nor to opposing Assad, thus only deepening the Syrian stalemate that contributed to ISIS' rise.
6. Obama doesn't want to build up the rebels enough to defeat ISIS, he doesn't want to invade and occupy Syria (rightly), and he doesn't trust Turkey enough to sponsor a Turkish invasion. With those options off the table, only Assad is left as someone who is able to re-conquer ISIS-held territory and occupy it for many years, which is what it would take to end the ISIS threat. So it looks increasingly likely that Obama will come to view Assad as his only real option if he wants to defeat ISIS.
7. Obama's priorities in Syria are crystal clear. He loathes Assad, but he's shown in action that he is far more concerned with countering jihadist threats to the United States than he is with stopping Assad's slaughters. He refused for years to intervene against Assad — denying calls from much of his cabinet, including then-Secretary of State Hillary Clinton, to do so — and slow-walked programs to arm the rebels. By contrast, Obama met the rise of ISIS with an extensive American bombing campaign in Iraq and in Syria. The jihadist threat, and not humanitarian catastrophe, is what ultimately motivated him to act.
8. Obama's Syria policy is already drifting toward supporting Assad. The Syrian regime is the perhaps the only consistent benefactor of the strikes. They've put Assad in a much better position in the Syrian civil war. This campaign has been so helpful to him that Assad's government claimed (falsely) to have helped coordinate it. Even in the status quo, if nothing changes, then Assad will be strong enough to stay in power — something Obama has clearly reconciled himself to — but not quite strong enough to defeat ISIS. Everybody loses.
9. Obama has proven more than willing to cross into dark territory when it comes to countering perceived terrorist threats. His vast drone strike campaign has far exceeded George W. Bush's, including with strikes against American citizens and "signature strikes" targeting people just for being a "fighting-age" male in the wrong place at the wrong time. He's partnered with dictators in Yemen and Algeria and elsewhere. Partnering with Assad would be a major step, but in a direction he's already going.
10. Unless ISIS miraculously collapses on its own or Obama changes the calculus that had led him to rule out every other option, then he ultimately has two choices. Keep the status quo strategy, accepting that it will leave ISIS pretty capable of attacking the US and American interests and will leave Assad in power, or partner with Assad and help him win the war. Both of those options are disasters for Syria and for the broader Middle East, not to mention for Obama's legacy. But only one of them actually achieves Obama's narrow objectives in Syria and is consistent with his approach to the Middle East. And, accept it or not, it's the path down which we are already heading.