War in Afghanistan ended with the collapse of the Soviet Union; but events in Afghanistan following the Soviet withdrawal created a new post-cold war threat for the world peace – the Taliban – which teamed up with Al-Qaeda to challenge the US hegemony on the eve of the twenty-first century. Even prior to the incidents of 9/11, the Al-Qaeda had attacked US installations in 1993, 1996, 1998, and 2000 – latter two of which were carried out while Al-Qaeda was headquartered in Afghanistan. Pakistan and Saudi Arabia were the primary supporters and sponsors of these two groups. Now the question arises that why didn’t the US do something about the Taliban during this phase? Why didn’t the US turn against the Taliban? Rather, they kept making offers including at times formal US recognition, if they handed over Osama bin Laden. Why didn’t the US put pressure on Pakistani and Saudi sponsors, or not supported anti-Taliban groups in Afghanistan, and why there was no hostility in the US towards Taliban regime prior to 9/11? There are several hackneyed clichés about it. This paper attempts to evaluate the one assuming the oil interests in Caspian Sea as the primary spoil of the game.