As for Reagan, his policies ultimately matter more than the image he (and his wife) created for himself. Certainly whatever personal deficiencies he might have had, they are dwarfed in comparison to what we are contending with in the present day. But he was the original catalyst that made such ideas part of the political mainstream, and given how things have played out in the half-century since his ascendance as a political force, that is not looking like a laudable legacy.
As for Woodrow Wilson, the great irony there is that he originally ran for President based on policies that not only did he not personally believe in, but that were nearly one hundred and eighty degrees removed from his actual views.
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