Bad vs. Worse: the worst voting dilemmas imaginable

(mods, I could see this in three or four different forums; move if necessary)

Inspired by the 2016 election: Give some examples of the most agonizing choices possible for a 2-party election; where no matter who wins, people will say “X could never have been elected if the opposition had been anyone other than Y”.

Here’s one example courtesy of Oglaf:

ETA: Real Life example: for the unlucky inhabitants of Eastern Europe 1941-1945 Hitler v. Stalin

Don’t blame me, I voted for Kodos.

I honestly can’t think of a worse match up than Clinton vs. Trump.

The 1920 presidential election was pretty much a contest between two people no one wanted. The Democrat, James Cox, was a progressive but totally colorless compromise who wasn’t nominated until the 44th ballot. The Republicans gave up after ten ballots and picked Warren Harding, handsome, genial, and totally corrupt.

Both of them were former newspaper executives from Ohio. Harding mostly ran against Woodrow Wilson and the League of Nations. Cox personally campaigned in 36 states and was rewarded with just 34% of the popular vote.

Cox turned out to be a much better publisher than politician, and built a successful newspaper chain which still exists. Harding had the good fortune to die just as all the scandals were coming to light. Both of them were soon eclipsed by their running mates - Calvin Coolidge and Franklin Roosevelt.

Whereas I would’ve said that Sanders v Trump would’ve been significantly worse.

My first presidential vote was in 1980, and in that time the only election I felt was a pick between the lesser of two bad choices was 1988. Every other election included a candidate I thought was a good choice—no lesser of two evils involved.

Rosie O’Donnell vs. Joe Arpaio
Lena Dunham vs. Sarah Palin
Oprah vs. Roy Moore
Kanye West vs. Rick Santorum
Michael Moore vs. Newt Gingrich
Stephen Colbert vs. Herman Cain
Soros vs. Kochs

Rosanne vs. Sarah Palin

Cruz v Trump was worse.

An American history professor I knew once described the outcome of the 1976 Presidential campaign (Carter over Ford) as electing “the evil of two lessers.”