What will be the Electoral College margin in the 2020 presidential election?

Buy NO on all Democratic positions

In general, I don’t endorse betting on President Donald Trump to win reelection this year, but if you feel the need to make that bet, this is the smartest way. Buying against every bracket for the Democrats effectively prices you in at a 22% chance that Trump wins reelection, with the added benefit that if you are wrong you will only lose in one bracket. This is a stark contrast to the marquee markets where Trump is priced in the 40s and your entire investment is at risk. This bet also works as catastrophic insurance if you are betting heavily on a big night for the Democrats and would like to cut some risk.

Which party will win the U.S. Senate election in Iowa in 2020?

Buy Democratic YES or Republican NO in the 40s

After three successive polls of varying quality showing Democrat Theresa Greenfield in the lead, smart traders are rushing to buy Joni Ernst, assuming this is the low point in the election cycle for the Republicans and this race in particular will soon revert to fundamentals. I make a lot of money betting against smart players. Those buying the Republican in this spot are making a lot of assumptions that I’m not yet willing to make: Namely that the economy will rebound, public sentiment will start to turn against the Black Lives Matter protestors and the worst of the COVID-19 crisis is behind us. If these factors continue to be a drag on the party into late summer, expect those with money on the Republican in Iowa to hit the eject button.

Who will win the 2020 Democratic vice presidential nomination?

Buy Tammy Duckworth and Kamala Harris for a combined 50¢

With all the ups and downs of the last few months, it’s hard to like any of the VP choices who have already had their moment in the sun. I still love Tammy Duckworth as a longshot bid, figuring that if we have a new crisis in the next month it would probably be military-related. In fact, the open criticism of Trump from top military brass already feels like the beginning of a new opening for Biden to run as a military and foreign policy favorite, an appeal that a Purple Heart recipient like Duckworth could help to fortify. I’m buying Duckworth for a big payday and will probably buy enough Harris to cover the bet, given that if the next month is unexciting, it will probably be her.

Insight into wagering on political prediction markets? Check out Luckbox’s The Political Trade wherever you listen to podcasts. Weekly episodes feature top prediction market traders and political insiders, including Rachel Bitecofer, Anthony Scaramucci and James Carville.