In this regard, Putin claims to have achieved his goals after five months of aerial bombardment, which include taking on the "terrorists" in order to save the Syrian regime.
Putin claims to have achieved his goals after five months of aerial bombardment, which include taking on the 'terrorists' in order to save the Syrian regime.
And while Russia's mainly aerial military intervention did prevent the collapse of the Bashar al-Assad regime, it proved insufficient to impose a Russian order in the country.
In any case, and regardless of whether Putin’s mission was indeed accomplished, the question remains: Did Putin prove Obama wrong on Syria? Or has he finally heeded Obama's advice?
Putin's calculus in Syria
Obama has warned his Russian counterpart against being bogged down in a second Afghanistan and urged him to work with and not against those trying to take on ISIL instead.
Contrary to the warnings of the Obama administration, Putin continued to support the Assad dictatorship at a great cost to Syria and the Syrian people.
His gamble in Syria did not backfire and the country did not turn into a Russian quagmire.
Putin, who seized on Obama's hesitation to deploy military force in Syria, had succeeded in pulling the rug from under the Obama administration to dictate the way forward towards a diplomatic solution, and to carve a new role for Russia in Syria and beyond.
Russian President Vladimir Putin [EPA]
Over the past five years, as Syria descended into a fully fledged civil war with tragic consequences to its people, Putin was steadfast in his support for the Syrian regime, while Obama has been reluctant, indecisive and weak.
Since he announced back in 2011 that Assad had to go, Obama did little - if anything at all - to make this happen. Syrians expected that when the leader of the world's superpower made such an assertion, it would have more value than if Joe the Plumber uttered it.
The armchair general
Obama was even reluctant to use power against the Assad regime's use of chemical weapons against its people. Even his supporters were disappointed; and his vice, Joe Biden, admitted: "Big nations don't bluff."
Moreover, Obama rejected the idea of a no-fly zone in northern Syria to protect the refugees. His support for those who Washington deems "moderate" has been terribly limited and inconsistent, just as his fight to "degrade and defeat" ISIL has been slow and unstrategic.
In short, unlike Putin, Obama has weighed all the angles and deliberated on the meaning and consequences of military actions after the two wars in Afghanistan and Iraq, and the military campaign in Libya. He examines all the scenarios, options and instruments available to him.
But unlike Putin, Obama did not act. His deliberation and consultation, like those of an armchair general, were mainly to spare and not to guide the US to take direct military action in Syria, other than against ISIL
One must not rush to a conclusion, as Russia will continue to maintain a serious military presence and bases in the future; it will continue to push for a friendly regime in Damascus. With oil prices dwindling, Putin doesn't have the surplus cash to fuel an open ended war in Syria.
The way forward
But the timing of the Russian decision to coincide with the opening of Syrian talks in Geneva this week underlines its political importance.
Putin's message to Assad may be read as follows: You can no longer bank on sustained Russian effort to defeat your enemies...
Putin's message to Assad may be read as follows: You can no longer bank on sustained Russian effort to defeat your enemies; you must instead negotiate in good faith a way out of the deadly civil war.
If Assad tries to outsmart the Russians by betting on his allies in Tehran to support his exigent stance, I would not be surprised if the Russians lifted their protection, and Assad ended up in the Hague on war crimes charges sooner rather than later.
Assad denies that he has any differences with Putin, but he is probably too cautious to make any pronouncements at this stage that might trigger Russian anger and lead to closer Russian-US realignment.
There are increasing signs that perhaps Putin and Obama are heading towards a more accommodating phase of Russian-US relations.
After all, while the calculating Obama was complaining about the Russian intervention, he has been trying through his Secretary of State John Kerry to turn the challenge of Putin's involvement into an opportunity that allows him to push forward with a co-chaired diplomatic process with better guarantees for success.
Putin might have played his cards right over the past six months, and his gamble could pay off diplomatically, but it will be Obama who will eventually cash in his chips, whether through sanctions relief, diplomatic empowerment or even cooperation in other areas of the region and the world.
Marwan Bishara is the senior political analyst at Al Jazeera. Follow him onFacebook.