The modern Democratic party has a bit of a history problem. The oldest political party in the world regularly celebrates Jefferson-Jackson Day dinners, yet both men are hardly taken as role models by today’s left-leaning Democratic party. Both were slaveholders, with Thomas Jefferson possibly fathering children with one of his slaves. Andrew Jackson, meanwhile, is further tarnished by his policies of Indian removal and forced relocation.
They are an uncomfortable reminder that, for much of its history, the Democratic party was the party of slavery, racial segregation, and white supremacy. That both Jefferson and Jackson were also skeptical of a strong centralized federal government only adds to the awkward position of these two flawed politicians in the Democratic pantheon.
Another black mark on the historical Democratic party has been the various corrupt political machines that governed American cities in the 19th and early 20th centuries (although, to be fair, there were some Republican machines as well). None is more famous than New York’s Tammany Hall—specifically, the Democratic party machine of Manhattan. And no Tammany figure is more notorious than William M. Tweed. Boss Tweed and Tammany have long been synonymous with graft, corruption, kickbacks, vice, stolen elections, and even violence. Tweed is still defined by the caricatures of him as an overweight, greedy schemer, as drawn by Thomas Nast.
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