U.S. President Barack Obama's interview on "60 Minutes" was one of the most challenging interviews that he has had during his tenure so far. What made the interview tough in particular was the question of Syria and his policy from the beginning of the crisis. In three different instances about three questions on Syria the interaction between Steve Kroft, the interviewer, and Obama became particularly tense. Kroft did not consider Obama's responses to questions about Syria persuasive, and as he pushed back they started to interrupt each other in an unusual way. The interview, the dynamic and Obama's responses demonstrated the question of Syria will continue to haunt Obama in his last 14 months in office and will do so after he leaves office.The first of these three issues was the fight against the Islamic State of Iraq and al-Sham (ISIS), which Obama launched with the formation of a coalition after ISIS captured Mosul. A few months after this unexpected development, Obama declared the strategy to degrade and destroy ISIS. Obama in part defended the record of his strategy by saying: "What we've been able to do is to stall [ISIS's] momentum to take away some of the key land that they were holding, to push back, particularly in Iraq, against some population centers that they threatened. And, in Syria, we've been able to disrupt a number of their operations." Obama also acknowledged: "We are not going to be able to get rid of them unless there is an environment inside of Syria and in portions of Iraq in which local populations, local Sunni populations, are working in a concerted way with us to get rid of them." There were some real problems about Obama's approach. On the one hand, he was expecting the local population in Syria and Iraq to help defeat ISIS, and on the other, he used to express his lack of confidence in the moderate opposition in Syria by saying: "Many of these people were farmers or dentists or maybe some radio reporters who didn't have a lot of experience fighting." However, after the fall of Mosul we have seen a serious change in the administration's approach to Syria and the reports about $500 million dollars for training and equipping the moderate opposition that the administration announced. We see a second problem in his approach regarding the moderate opposition in a debate on the fate of train-and-equip program.The fate of the train-and-equip program led to the second tense moment in the interview. Obama said: "My goal has been to try to test the proposition, can we be able to train and equip a moderate opposition that's willing to fight [ISIS]? And what we've learned is that as long as [Syrian President Bashar] Assad remains in power, it is very difficult to get those folks to focus their attention on [ISIS]." In fact, Obama indicated that he was skeptical about the train-and-equip program from the beginning and also demonstrated that despite the contrary argument of almost every observer, he believed that he could form a group of well-trained ground forces that would not focus on Assad while Assad continues attacks on the oppositions and civilians in Syria and instead focus solely on the fight against ISIS. Kroft was increasingly insistent about this question and at this point called the failure of the program "an embarrassment," and Obama accepted that it did not work. In the last year the program had some serious setbacks because of unrealistic expectations, such as expecting members of the moderate opposition to give a pledge to only fight against ISIS and not against Assad. On top of all that, the fate of the around 60 people - the expectation was to train more than 5,000 - who were trained in this program is still not clear.The final disagreement between Kroft and Obama was regarding a question about Russia's actions in Syria. Obama particularly seemed uneasy when Kroft argued that Russian President Vladimir Putin challenges American leadership. Obama stuck to his talking points about Russian involvement and said this involvement is not a show of strength, but rather an indication of weakness on the part of Russia. Obama gave a cautious respond for a prediction of Russian action in Syria. He said the U.S. had good intelligence, but when Kroft asked him if the U.S. knew what Russia was planning to do, Obama said: "We knew that he [Putin] was planning to provide the military assistance that Assad was needing because they were nervous about a potential imminent collapse of the regime." It is still not clear how much the U.S. knew about a possible Russian military buildup in Syria, however in terms of geopolitics of the region it is already considered a game changer. If U.S. policy about this development will be to wait for Russia to drown in the Syrian quagmire, it will be perceived as an excuse for further inaction instead of a strategy by the many U.S. allies in the region.As the situation in Syria becomes more complicated, Obama is trying to manage the public perception of the crisis, especially after the Russian airstrikes. His press conferences and TV interviews are becoming a little bit tenser when the topic comes to Syria. It seems that we will see such tense press conferences and interviews more often in the next 14 months.