What about an alternative Election 2000 scenario in which there's a 269-269 electoral college tie, and the House deadlocks on electing a president, but the Senate elects Lieberman as VP....thus causing Lieberman to step in as acting prez? 9/11 and the beginning of the War on Terror then happens at a time when the POTUS is a Democratic hawk, who also happens to be Jewish.
Or Gore wins in 2000 and happens to be visiting the Pentagon on September 11.
Actually, that one's a really good idea. An alt-timeline in which the president dies on 9/11, and the VP has to take over. You could either change the details of the 9/11 plot so that the assassination was planned, or you could make it a coincidence.