I wrote a piece on Bush in Sunday's Los Angeles Times which compared him to Woodrow Wilson. A number of people have questioned the comparison, so I thought it useful to open a broader conversation. (A more detailed discussion is in my new book, The Powers to Lead.)
Wilson and Bush have many similarities. Both were highly religious men who came to office without experience in foreign policy and responded to a crisis with a bold moralistic vision. Many of Bush's speeches about promoting democracy could have been given by Wilson. Both men proposed policies that had a great gap between expressed ideals and national capacities. Both were stubborn. As one of Wilson's advisors said, "once a decision is made it is final. There is no moving him after that." Wilson was offered a compromise that would have led the Senate to ratify American membership in the League of Nations, but he adamantly refused. Bush, of course, has been notoriously stubborn about his Iraq War and thinks that history will absolve him as it did Wilson and Harry Truman.
In judging leaders, there is always a question of luck. Wilson was unlucky that a stroke crippled him in the midst of his campaign to educate the American public about the League of Nations. Ironically, had the stroke killed him, the Senate would almost certainly have ratified a version of his League and he would have left office (posthumously) as a hero. Instead, his stubbornness meant that his policies were rejected, and isolationism crippled American foreign policy for the next twenty years. Eventually, Wilson's reputation was rescued by World War II and the creation of the United Nations.
I doubt Bush will be as lucky in the long run. Some dimensions of luck are purely fortuitous, but people also help to make their luck. Reckless reality-testing and unnecessary risk-taking are often part of "bad luck".
Future historians are likely to fault Bush for reckless reality testing, and going it alone. As the Canadian political leader Michael Ignatieff puts it, "it was not merely that the president did not take the care to understand Iraq. He also did not take the care to understand himself." Good coaches analyze their game and their opponent's game so that they can capitalize on errors and benefit from "good luck." History tends to be unkind to the unlucky, but historians also judge leaders in terms of the causes of their luck. Wilson was stubborn, but not reckless or unilateral. He entered World War I reluctantly and sought a multilateral solution at the end.
Even if fortuitous events lead to a better Middle East twenty years from now, future historians will criticize the way Bush distributed the risks and costs of his actions. People who try to climb Mt. Everest accept a degree of risk, but a team leader still has to make sure that the whole group understands the balance between risk and achievement. It is one thing to pose a grand vision that leads people up a mountain; it is another to lead them too close to the edge of a cliff. Wilson was lucky that the outcome of World War II rescued his League idea. But even if the Middle East is better twenty years from now, historians will ask if it is because or in spite of Bush's actions.