Great counterfactual:. Suppose Clay had beaten Polk in the 1844 election (most historians think the votes for a third party cost him the electoral votes he needed to win). Clay was opposed to the annexation of Texas. That precipitated the Mexican American war. Absent the subsequent expansion of territory, the 1820 Missouri compromise would have remained in force. No controversy over slavery in the Territories.
I think it is one of the great ironies in history that the party that cost Clay that election was a single issue anti-slavery party. Again, that is a counterfactual.
I think, counterfactuals can be helpful in at least one respect. They highlight the contingencies of history. Viewing it as an inevitable process lets individual actors off the hook. Taking full account of the choices available to them at the time, we are, as readers and thoughtful citizens, entitled to make judgments as to whether what they did was smart or stupid, moral of immoral, etc. and apply those judgments to the events of our day if we are so inclined.
In that vein, IMO, the greatest work of American history written in the 20th Century was authored by a philosopher, Harry Jaffe, Crisis of the House Divided. Notionally, it is about the Lincoln Douglas debates. It is something of a demanding read, but by no means impossible. Not along the lines of what Jay was looking for, but it reminds me that regardless of how exceptional America might be or not, we still struggle with finding the answers to some of the fundamental questions about politics that would have been familiar to Plato.
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