Turkey and Israel enjoyed an almost perfect relationship throughout the 1990s that amazed their friends, yet bothered their rivals. The US war in Iraq revealed, however, that the two longstanding allies did indeed have contradictory objectives and concerns with respect to the future restructuring of Iraq. While Turkey fears the emergence of an independent Kurdish state in northern Iraq, the same possibility seems favorable for Israel from its security standpoint, vis-à-vis threats posed by countries like Iran, Pakistan, and beyond. It appears that the "amazing alliance" is heading toward a crossroads. Such an eventuality may change the nature of the relationship from a "win-win" to a "lose-lose" situation unless proper steps are rapidly taken with a view toward rebuilding confidence on both sides.