Yes, but when they would settle the rules of the bet, Taleb's confusion between nowcast and forecast would have to go away and what they would use to base their bet then? Losing an argument is as bad as losing a bet. I don't think Taleb want's to acknowledge that he was picking a fight for nothing.
Note: I'm don't think Taleb has a wrong idea. It's just that he attempt to fight with Silver over it is based on confusion. Taleb has written important and interesting books and papers. He has always been very opinionated and aggressive. His feuds don't produce debates that are worth following.
Election Predictions as Martingales: An Arbitrage Approach, Nassim Nicholas Taleb Quantitative Finance. 452 (1): 1–5. doi:10.1080/14697688.2017.1395230
https://arxiv.org/abs/1703.06351
Nate calls the chances like 80:20 Clinton:Trump.
Taleb takes the side: 100,000 USD that Trump wins.
If Trump wins, Nate pays 500,000 to Taleb. If Clinton wins, than Taleb pays 100,000 USD to Nate.
But that doesn't seem to be the nature of their disagreement. Taleb's main complaint seems to be about how the swings in the prediction probabilities far out from the event indicates a fundamental flaw in how the underlying model uses probability.
That being said it would be a fun little exercise to see who much money would be made if they bet had $1 on every race 538 predicted in 2016 and 2018 using the model odds.
Indeed after skimming through the paper[1] (I find it hard to grasp without a solid background) it seems that Taleb wants to play this game every day before the election and expects to come out ahead on election day when all the bets are settled.
