Bryan Caplan has a formidable track record at winning bets I Win All My Ebola Bets
Some of these bets are obvious. Easy money can be made betting against crisis, than for, as I have demonstrated in my own personal investments/bets in the stock market.
Most people it would seem overestimate the odds of drastic negative events (such as Trump being impeached, Ebola pandemic, market crash, hyperinflation, recession, etc.) Negativity bias probably plays a role. It’s easier to take the opposite side of a negative bet (predicting that something bad won’t happen) than predicting that something will happen.
The media is impartial, not just in terms of the political biases of the journalists and staff, but also how the influence of advertising dollars skews reporting and leads to the dissemination of narratives that are profitable but inaccurate and or implausible. Negativity, which generates more advertising due to increased pageviews and ad-clicks, tends to be amplified, but optimism, which is less profitable, is suppressed, even if the optimistic outcome is more probable and backed by evidence. Bryan Caplan is so good at betting because he bets in favor of the most probable outcome, not the outcome that is touted by the media.