Trump now faces a daunting decision: Does he escalate the conflict to try to achieve his ambitious goals, no matter how unpopular with the American people? Or does he declare some sort of victory and execute a quick withdrawal, minimizing the economic damage but leaving behind an embittered, violent regime with the materials to someday build a nuclear weapon? The eventual outcome may come down to just how much risk Trump is willing to accept—and how much pain he is willing to take.