After the fall of Saddam Hussein, and fuelled by hatred towards the US, several radical militant groups emerged in Iraq. A particular Sunni group, ISI (Islamic State of Iraq) materialized and led infamous attacks against US and Iraqi targets. The US killed the group's first leader, Abu Musab Al-Zarqawi, in 2006, and, in collaboration with the Iraqi army, killed its second leader Abu Omar Al-Baghdadi in 2010. In 2011, the US pulled out of Iraq leaving it to its own destiny. When clashes erupted in Syria, the world went against the Syrian President Assad. While Assad refused to abandon power hoping to crush the opposition, Syria became a warzone. Thousands died; millions fled. The group, ISI (Islamic State of Iraq), preying on the weak, utilized the Syrian conflict to its advantage and expanded into Syria as ISIL (Islamic State of Levant). A transnational threat exported from Iraq, ISIL battled both the opposition and Assad. Amidst its militants were Arabs, Afghanis, Britons, and Europeans. ISIL became a power to reckon with. It gained a hold of approximately 35% of Syria. It then crossed back into Iraq. The Iraqi army, trained and equipped by the US Forces, but proven to be extremely weak, surrendered instantly. ISIL overran Mosul, Tikrit, and other strategic areas; attacked oil-rich Kurdish areas; became ISIS, (Islamic State of Iraq and Syria); and finally morphed itself into IS (the Islamic State) implying a wider spread of power. It even landed itself a caliphate, Abou Bakr Al-Baghdadi. Now, as the Huffington Post claims, the Islamic State has between 13,000 to 35,000 square miles under its auspices in Iraq and Syria, with its militants ranging between 30,000 to 50,000 fighters. Having ignored ISIS in Syria, turning a blind eye to its coldhearted beheadings and callous pursuit of power, the US could not ignore its national interests in Kurdistan, in north-eastern Iraq. Erbil, the capital, was being threatened. The US led air strikes against the Islamic State and airdropped food and water to thousands of Yazidis, a minority group living in northern Iraq, who had flurried into Mount Sinjar and got stranded. The US had to also acknowledge the threats of westerners who joined the Islamic State and would possibly return to the West to inflict terror. Now the US has come to realize that the Islamic State menace spans the whole region and will ultimately bypass borders into other territories maybe even as far as the West. And the US has come to realize, too, that indeed to finish off the Islamic State, it may have to go after it in Syria. And here is the dilemma. Does the US let bygones be bygones and work with its enemy, Assad, the man who killed almost 200,000 Syrians, most of them civilians? Better yet, does the US ask for Assad's permission and approval to attack Syrian land or does it go alone into Syria unheeding Syria sovereign premises? Most importantly, will the enemy's enemy become a friend as the saying goes? It is complicated. The US sided with the FSA (Free Syrian Army) against Assad supplying it with arms. The Congress is yet to vote on how to punish Assad on his alleged use of chemical weapons on his own people. And yet, the US is ready to side with Assad against IS even if in theory. And Syria, though ready to accept the US intervention, has announced that carrying out air strikes without its consent would be considered an aggression. The Russians side with Assad and so does Iran. Both countries would consider an-unsupported-by-the Syrian-government attack a hostile action, which may lead to even worse confrontations. Besides, the US cannot risk having its planes shot by Assad's army, so it needs Assad's affirmative nod for such strikes. In hindsight, Assad was never a direct threat to the US and was never involved in any conspicuous events against the US. By comparison, the Islamic State has targeted the US in its hate speech quite openly; hence, the better of two evils rules. The US has already started the confrontation with surveillance flights over Syria; the Syrian reaction has yet to unfold. Simultaneously, the US doesn't seem as though it will hold geographic borders as an issue in its pursuance of the Islamic State. Unpredictable days lie ahead.