Some additional thoughts.
1. I realize Jefferson and Madison were not particularly effective in office. But the Federalists were responsible for the Alien & Sedition Acts, the greatest threat to freedom this country has ever faced, outside of slavery. The Federalists are dead to me after that. That’s why there is absolutely no way I could vote for DeWitt Clinton in 1812 or especially Charles Pinckney in 1804. Noon has a theory about why Clinton was actually a pretty good choice which he can explain if he wants. But let’s remember that this is before the Erie Canal so he doesn’t have this under his belt yet. And with Pinckney, well, that’s just way too soon for the Federalists–even knowing that Jefferson’s Embargo was arguably the worst foreign policy mistake in the nation’s history.
2. I do agree across the board about Henry Clay, who was simply a better candidate than anyone else for most of those elections, outside of arguably 1824 when a John Quincy Adams vote could make sense. On the other hand, while Van Buren was indeed a pretty awful president, Daniel Webster is not great vote. Webster was the ultimate pre-Civil War plutocrat and while personally opposed to slavery, voted for the Fugitive Slave Act. I mean, you do what you have to do sometimes, but what a nose-holder.
3. On the other hand, 1856, now that’s a bad election. Really the worst in American history. Which says something given the stiff competition for this title. Who do you choose here? I mean, I guess you have to go with Fremont because Buchanan and Fillmore are both so odious. But Fremont’s utter incompetence in everything he ever did makes George W. Bush look like George Washington. To quote Richard White’s bit on Fremont from Railroaded “By the early 1870s, Fremont was a man so expert at transmuting opportunity into spectacular disaster that he was not only capable of squandering a gold mine but actually did squander one.” Said Jay Cooke of the man, “Fremont is entirely unreliable in money matters and it injures any one to have any connection with him.” Cooke didn’t say this because Fremont had the morals Cooke so very much did not; Fremont wanted to rip off the public as much as Cooke. He just wasn’t any good at it. Really his greatest accomplishment was an interesting daughter. His presidency would have almost certainly been an unmitigated disaster.
4. I respect going to the Bryan well all three times. Everyone forgets that Bryan was actually a tremendously principled man who attempted to do a lot of good in the world. Yes he was a fundamentalist Christian who embarrassed himself in 1925 during the Scopes Trial. He was also ejected from the Wilson Administration for not going along with the increasingly militarism of Wilson. Does that not buy him credibility? Plus, TR is the most overrated president in history.
Really can’t disagree that strongly going forward except to say that while Harding was lame, so was James Cox. Again, no good choice there. Also, I’d go with the underrated Charles Evans Hughes over Wilson. The politics of the late 20th century are too boring for me to argue about much. The idea that Howard Dean was some kind of great progressive is not actually supported by any evidence, but then neither are a lot of annoying myths.