On December 17, 1862, as the Civil War entered its second winter, General Ulysses S. Grant issued General Orders #11, expelling “Jews as a class” from his war zone. It remains the most notorious anti-Jewish official order in American history. The order came back to haunt Grant in 1868 when he ran for president. Never before had Jews been so widely noticed in a presidential contest, and never before had they been confronted so publicly with the question of how to balance their “American” and “Jewish” interests. During his two terms in the White House, the memory of the “obnoxious order” shaped Grant’s relationship with the American Jewish community. Surprisingly, he did more for Jews than any other president to his time. How this happened, and why, sheds new light on one of our most enigmatic presidents, on the Jews of his day, and on America itself.