Found this great satirical piece at The Gadflyer that offers a scenario of * as president during WWII. My favorite quote:
'General Eisenhower, after weeks of asking for a meeting with the President, is finally escorted in to the Oval Office, where he is shocked to find out that W has been meeting with General MacArthur, devising a detailed plan to invade Soviet Manchuria immediately.
The strategy of invading Soviet Manchuria catches the world by surprise, but W sells the American public on the idea by citing the need to defeat all the world's menacing totalitarians – Hitler, Tojo, and Stalin. After all, he says, Stalin's worldwide Bolshevik revolution was as much a totalitarian threat to the United States as the Empire of Japan or the Third Reich.
Uhhhh, the Gadflyer Newspaper would write, but Stalin and Hitler don't really get along, and the Soviets and Japanese were historic enemies dating back to the Russo-Japanese War. And even if invading the Eastern Soviet Union were a good idea, one might have argued, total defeat Tojo and Hitler must be the immediate priority.
Bull! Our cowboy president would reply. An Evildoer is an Evildoer, and besides, Stalin tried to have his grandpappy Prescott Bush and the rest of Brown Brothers Harriman during a prospecting visit to the USSR in the 20s.'
http://gadflyer.com/articles/?ArticleID=127