U.S. President Barack Obama told an interviewer recently that the humanitarian catastrophe in Syria “haunts me constantly” — and well it should. Hundreds of thousands dead, millions displaced, and still no end to the conflict is in sight. Even one year ago American military power still might have intervened decisively, without engaging America in another land war. Thousands of Syrian lives might have been saved.

Obama’s geopolitical strategy is also going badly. What once seemed a hopeless stalemate between what remains of the regime of Bashar Assad and various anti-Assad forces changed dramatically when Russian air power entered the war.

The turn against American influence began not yesterday but in fact three years ago, amid what seemed at least to Obama to be a successful turn of events.

Red lines and bad bets

In September 2013, against Obama’s famous “red line” vow to punish Assad for using chemical weapons against rebel forces, Putin at the last minute unexpectedly secured Assad’s promise to give up Syria’s chemical weapons in order to avoid American action. Obama, thinking that Putin had sealed for him a victory much larger than what a “pinprick” attack could have achieved, made a bet that he could do business with Putin, in Syria and perhaps elsewhere. America and Russia could become allies, even partners, in pacifying a Middle East in chaos.

This wager has failed, a fateful misreading of the Russian leader. Putin’s Syria policy became more ambitious and bold over the past two years while Obama’s reluctance to commit to greater military and humanitarian action solidified — no cratering Assad’s air force runways, no safe zones or no-fly zones. Russia’s airpower gradually changed military facts on the ground to the extent that Putin’s decisions are now central to Syria. He wants to take Aleppo within the next few months, changing the landscape faced by the next American president. Washington is effectively sidelined except for the continuing battle to destroy the Islamic State.

As part of the deal on chemical weapons, Obama believed Putin had committed to join the fight against the Islamic State. Assad would go, one way or another. Not immediately as a precursor to negotiations for a post-Assad Syria, but rather in some reasonable timeframe. Perhaps Putin did in fact commit to Obama. But as the military situation changed so did Putin’s plans.

As Russian air power bolstered Assad’s position, he wasn’t winning but he was no longer losing. As Obama temporized, Putin saw an opportunity.

By escalating his military engagement in Syria, Putin gradually pushed American influence aside. He raised the military stakes and in effect Obama has been played in Putin’s game of on-again, off-again diplomatic cooperation. Finally this month Washington announced it was getting out of the game. It was too little too late.

Aims and means

What does Putin want in Syria? Above all, stabilization of the country, which means ending the war. Putin is in no way wedded to Assad and will drop him at an opportune moment, as Assad well knows. Putin needs Assad in power for the foreseeable future, but only to serve Russian policy. He knows that Assad, with so much blood on his hands, cannot be Syria’s enduring leader.

Ending the war means the various anti-Assad rebel groups have to be beaten into submission, at least until they accept a peace negotiation with Assad at the table. Thus, for the time being the carnage must go on.

At the same time, setting up a functioning governmental structure requires destroying the Islamic State on Syrian territory. Putin has said many times that Russia cannot accept a kind of Libya, a failed state prey to Islamist terrorists, in its sphere of influence. Even though there’s no common border, Russia would be threatened so long as Islamic State controls Syrian territory. Thus, in a sense Obama’s focus on destroying the Islamic State now does Putin’s work.

Putin’s longer-term intention is to re-establish Russian influence in the Middle East. Syria as a Russian client state on the Mediterranean Sea, already hosts Russia’s only naval port in the region, at Latakia. A permanent Russian troop deployment is being considered. Russian influence in Syria drives Moscow into obvious tension with Iran, though for the moment Tehran is Moscow’s ally in supporting Assad.

What does Obama want in dealing with the Syrian disaster? How can he deal with Putin’s geopolitics?

Obama came to office eight years ago determined to end America’s two wars, the agonizing Bush legacies in Afghanistan and Iraq. He wanted to move America beyond a political culture of “permanent war.” He could focus on rebuilding America after the financial crisis and recession.

Entering the Syrian war with a major land force was unthinkable, and Obama has never wavered on this point. The danger of escalation to a full-scale land war explains his resistance to the urgings of Secretary of State John Kerry, former secretary Hillary Clinton, and many others in his administration to do more given the humanitarian consequences of doing less.

Obama’s highest priority in 2014-2015 remained the Islamic State. Many have forgotten how dangerous the Islamic State was thought to be, how it made sense to focus there in the midst of a civil war that the anti-Assad rebels seemed to be winning on their own. ISIS barbarism and fear that Islamist terrorists would strike the United States galvanized American public support for this policy.

Behind policies stand people

Obama’s problem in dealing with Putin goes deeper, however, to personal character and past experience. Obama is deeply American and Putin deeply Russian, steeped in Russian history and the Soviet experience.

In the interview cited above, Obama wonders aloud about what he might have done differently in Syria. He mentions Churchill and Eisenhower, wondering whether these giants of geopolitics would have seen some way forward that he could not. This sounds like humility, but it also sounds like a leader seeking cover, a man who suspects he was outmaneuvered.

Obama was surprised by Republican intransigence in 2009-2010, thinking the dire circumstances of the financial crisis would create a bipartisan spirit. He seems likewise surprised by Putin’s game in Syria (and also Ukraine). He thought Putin had committed to him. Instead, Putin had decided to become the main outside force in Syria..

Obama is not intellectually naive, but his history with Putin indicates an unwillingness or even an incapacity for brutality. Machiavelli wrote in The Prince that the leader who tries to be good in a world where so many others are bad “will necessarily come to grief.”

Amorality is not Obama’s strong suit in any case. He cares about “the problem of dirty hands.” Yet Putin is not evil in the sense that Hitler was evil. He doesn’t have delusions of world domination, nor is he genocidal. But he does believe that bombing and starving thousands of helpless civilians is justifiable to a sufficient Russian strategic ambition.

Putin is a former KGB man who served the Soviet Union for years abroad during the Cold War, especially in East Germany. His German is fluent — Obama speaks no other language fluently — and he is cosmopolitan in a way Obama is not, thoroughly at home in a world of government leaders populated by many power-seekers and liars. As a Dresden station chief he endured the Soviet Union’s collapse in the streets.

Obama’s past by contrast involves a youthful search for identity, that of a community organizer seeking common ground, a law school professor teaching rights and obligations, and a talented writer much given to introspection.

In terms of competitive instinct, Putin is a 5th degree judo black belt whereas Obama’s sport is basketball; a suggestive contrast.