I guess in thinking about this I realize it's so hard to even know if someone is a "PR disaster" that I probably have just been confirming my biases. What makes you say that he hasn't been?

It has very little to do with the forum. I don't think most people here that think they might be interacting with the executive branch would post anything super negative on the internet if they are thinking clearly. 

If I'm willing to bet, I need to take "edge". 

This is pretty patronizing. You don't know me but do you really think the average person on the EA forum needs that explained?

hence why I wrote 1/20 (95-5). If you believe the chance is <1/100 you are 10x. Given the asymmetry of my/other users knowledge of your internal probability, I understand offering the best possible odds for yourself that you still think the other side would take, but it's a bit of an icky norm to come on here and play poker when people might assume you would be happy to take a 2x-5x bet. More importantly the bet you offered proves nothing in my mind since anywhere between a 1-5% chance of the next election being rigged would still be really really bad and worth hyperventilating about. 

If you want, read my comment to lark. I don't think my resolution criteria are good. It's rather that I don't personally expect the next election to be rigged ( I would be on the same side of the 90/10 bet as you) but I do expect trump to continue to denigrate the checks and balances that we have in this country, whether it be official laws or unofficial norms, hence why I am trying to pose intermediate questions. I'll try to improve the original questions though. 

1/2 - just specify a specific crime that we think most presidents don't commit and would obviously be worth prosecuting. 

3 - really? You think this wouldn't be a clear step towards autocracy?

4 - The general position of MAGA's is that the 2020 election was stolen. 
5- Admittedly a Pretty awful market, just ignore this one 

Again I don't think even these modified versions are good, but I think we can still do better. 

Completely agree - I think all of my markets are bad. However the direction I'm trying to move in by proposing these questions is to operationalize steps along the way towards autocracy. You could semi replicate this but saying ok well will one of the next 5 elections going to be rigged (if you believe you can operationalize this), but even if you could set up a futures market for it I don't think you will get all that much market efficiency from it. 

Betting on the prob of next election is going to paint a very incomplete picture. There is a world in which we are 99% the next election is not going to get rigged but acts during this admin would credibly increase the chance of future riggings by a lot. For instance lets assume trump himself as no interest in being an autocrat. Then he wouldn't rig the election purposely right? And yet the fact that we now have a precedent that you won't be prosecuted for essentially anything if you win the presidency surely changes the incentives of future politicians who are considering meddling. 

This is literally my position. I think the next election is >90% to be "relatively fair", but I also think trump is going to do a ton of stuff that paves the way for a future election to not be fair. Picture below to help explain thesis.

Side note - I think you will not get full honesty from many people here (more likely they just won't comment). Anyone with a public reputation that wants to interact with trump's admin is not going to want to comment (for good reason), plus this subject can be a bit touchy anyway. 

how about 99/1? pretty wild to me that you would say

I have generally found the fears of democracy failing in the US to be hyperbolic and without much good evidence. The claims are also very "vibes-based" and/or partisan rather than at the object level.

and then only offer 90/10 odds. Are you saying you think there is a ~1 in 20 chance the next election is not going to be free and fair? I would not consider freaking about about 1/100 to be hyperbolic, much less 1/20.

Also It would be nice to break this up a little bit more. Here are some things I would probably bet you on, though they need to be clarified and thought out a bit more. 

• Trump will commit more than x crimes during his presidency. 
• Trumps secretaries will commit more than x crimes during his presidency
• Trump will attempt to run for a third term 
• The winner of the republican primary in the next two presidential elections will be a MAGA
• In the next x years, a future president or (sufficiently) high up politician will not be convicted of any crimes conditional on their party controlling the justice department

How do you feel about EA's investing in AI companies with their personal portfolio?

Hmm, I hear what you are saying but that could easily be attributed to some mix of 

(1) he has really good/convincing ideas 

(2) he seems to be a a public representative for the EA/LW community for a journalist on the outside.

And I'm responding to someone saying that we are in "phase 3" - that is to say people in the public are listening to us - so I guess I'm not extremely concerned about him not being able to draw attention or convince people. I'm more just generally worried that people like him are not who we should be promoting to positions of power, even if those are de jure positions. 

| and there also isn't a robust pipeline for promoting virtues and virtuous actors to such places.

this ^