Crashing early is better than crashing later because it limits the damage and moderately frequent crashes creates some level of caution in the market. Propping up a market because it's too big to fail can in some cases create worse fallout. It's a judgement call though and I'm not entirely sure we have a really good rule of thumb here.

If there were a way to have enough transparency that we had smaller crashes more frequently it would probably help to limit the damage to those who can afford to lose it.

The truth is that you can only push a correction so far out. It will happen eventually and the farther out you push it the worse it will be.

Also, I doubt you can predict a crash and make bank on it without having a whole bunch of people point in your direction. You'd have to have been speaking about it publicly prior to and have had zero inside information on some too-big-to-fail organization failing. I know people feel the US justice system doesn't hold the wealthy accountable, but I also think the wealthy are pretty good at knowing where the line is drawn. You can have all the money in the world but it's no fun if everyone's out to get you.

Negative-sum events are extremely popular with the winning side, and the winnings are momey, which converts to power.