I have made good money in election wagers over the years. I did, however, miss the opportunity (ties) of a lifetime when Trump versus Hilary. If you read the tea leaves even halfway, there were multiple points of arbitrage where you could have swung money back and forth with minimal risk. I did nothing, and it was the easiest money-maker election I have seen in my lifetime.

I would hesitate to attempt that this election cycle simply because the principals are so old. This looks like more of a Dead Pool opportunity than an election-betting opportunity.