Prospects for democracy in Iraq should be assessed in light of the historical precedents of nations with comparable political experiences. Saddam Hussein’s Iraq was an unusually extreme autocracy, which lasted an unusually long time. Since the end of the nineteenth century, only thirty nations have experienced an autocracy as extreme as Iraq’s for a period exceeding two decades. The subsequent political experience of those nations offers a pessimistic forecast for Iraq and similar nations. Only seven of the thirty are now democratic, and only two of them have become established democracies; the democratic experiments in the other five are still in progress. Among the seven, the average time required to transit the path from extreme autocracy to coherent, albeit precarious, democracy has been fifty years, and only two have managed this transition in fewer than twenty-five years. Even this sober assessment is probably too optimistic, because Iraq lacks the structural conditions that theory and evidence indicate have been necessary for successful democratic transitions in the past. Thus, the odds of Iraq achieving democracy in the next quarter century are close to zero, at best about two in thirty, but probably far less.