The perennial question “What if…?” can be the start of an interesting thought experiment, a creative work of fiction or a detailed exploration of historical contingencies. But counterfactual historical narratives are not without dangers, as writing history is always a political act. We will explore the different phenomena of counterfactual history as part of the way US Americans make sense of their past(s) and we will think about the practical and philosophical implication of asking “What If…?”.