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Bales and Freedman: Why We Just Bet On Oprah to Win in 2020

We (Jonathan Bales and Matthew Freedman) just bet our entire Bitcoin holdings on Oprah Winfrey to win the 2020 U.S. Presidential Election at +8000 at MyBookie. (Bales note: I for sure did not bet all my BTC on this.)

Why would we bet all our BTC on Oprah?

  1. We don’t own that much BTC. We prefer altcoins.
  2. #Arbitrage: Oprah is +220 to win at BetDSI.
  3. We think she has way better than an 80-to-1 chance to win. Her implied odds at MyBookie are 1.25 percent. It’s hard to create actual odds for outliers, but we’d say her odds are closer to five percent than to 1.25, which makes this a +EV bet.

I mean, at least one of us was willing to bet on Oprah at way worse odds.

Here’s the quick-and-dirty thesis for our Oprah investment.

Precedent

We no longer exist in a world in which it’s unthinkable for a billionaire TV personality to be president. There’s now a precedent for it. Oprah would not be a Black Swan. Rather, she would be the Democrat answer to the question raised by Donald Trump’s presidency. Also, given that I (Bales) bet on Trump to win $75,000 at 150-to-1 odds, I basically have to bet on Oprah now because of the #brand, but the market is still undervaluing unconventional candidates.

People Want to Vote for People They Don’t Dislike

President Trump still has his supporters, and he’s, like, really smart, but right now his approval rating is just 38.7 percent (per FiveThirtyEight). He endorsed Republican Roy Moore in the 2017 special election in Alabama for the Senate seat vacated by Jeff Sessions — even after Moore was accused by multiple women of sexual misconduct and assault over a period of years — and Moore lost to the Democratic candidate Doug Jones. Trump might have a hard time winning the general election anyway, and the public’s response to Moore last year and to Hillary Rodham Clinton the year prior suggests that people are actively choosing not to vote for candidates they dislike. Right now, 55.0 percent of all people polled disapprove of Trump.

People Like Oprah

This point seems obvious. People — all sorts of people — like Oprah. She’s real. She grew up poor and built herself into a mogul. She’s not an elitist: She was born in Mississippi, and raised in Milwaukee. Her first on-air opportunity was in Tennessee, and she built her media empire in Chicago, not New York or Los Angeles. She’s not famous for being in movies. She’s famous for being herself — and she’s the embodiment of the American Dream. Unlike many other celebrities, she has the ability to appeal to people all over the country.

If Oprah were to run, she’d probably have better voter turnout than HRC had — she’d almost certainly draw more people of color — and she’d also have a better chance of attracting moderate voters, especially women. If she runs, she has an underappreciated chance of winning both the Democratic nomination and the general election.

Oprah Might Actually Run

In the past Oprah has downplayed the possibility of running for president, but on Sunday night Oprah did this at the Golden Globes.

Freedman: I can’t watch that without crying.
Bales: I’ve never cried.

In the wake of Oprah’s speech, major media outlets have reported that Oprah’s close friends, confidants, and advisers are urging her to run in 2020 and that she is seriously considering it.

And why shouldn’t she?

The Democrats Need a Champion

Right now, the Democrats have no one who is a clear frontrunner. They have no one who has unified the party. This isn’t to say that they don’t have a number of people who could serve as perfectly respectable candidates, but they’re not particularly exciting. They all seem beatable — and the Dems want to win. There’s no clear candidate to keep Oprah from entering the race, and if she were to do so she would probably be welcomed as a potential savior by the left.

Are You Interested in a Freeroll?

As noted earlier, Oprah is +220 to win at BetDSI. She’s also -270 not to win. We typically don’t hedge, but there is an arbitrage opportunity here for people who want to limit their risk.

There might be yes/no props available at other books — as always do your research — but for the purposes of explanation let’s say that you could place the following bets.

  • $10 on Oprah to win in 2020 at +8,000 (MyBookie)
  • $27 on Oprah not to win in 2020 at -270 (BetDSI)

If Oprah were to win, you’d win $773 ($800 minus $27). If Oprah were not to win you’d win nothing ($10 minus $10). Again, evaluate all situations for yourself, but freerolling Oprah in 2020 . . .

. . . seems like a relatively non-donkey thing to do.

Photo Credit: Paul Drinkwater/NBC Handout via USA TODAY NETWORK

We (Jonathan Bales and Matthew Freedman) just bet our entire Bitcoin holdings on Oprah Winfrey to win the 2020 U.S. Presidential Election at +8000 at MyBookie. (Bales note: I for sure did not bet all my BTC on this.)

Why would we bet all our BTC on Oprah?

  1. We don’t own that much BTC. We prefer altcoins.
  2. #Arbitrage: Oprah is +220 to win at BetDSI.
  3. We think she has way better than an 80-to-1 chance to win. Her implied odds at MyBookie are 1.25 percent. It’s hard to create actual odds for outliers, but we’d say her odds are closer to five percent than to 1.25, which makes this a +EV bet.

I mean, at least one of us was willing to bet on Oprah at way worse odds.

Here’s the quick-and-dirty thesis for our Oprah investment.

Precedent

We no longer exist in a world in which it’s unthinkable for a billionaire TV personality to be president. There’s now a precedent for it. Oprah would not be a Black Swan. Rather, she would be the Democrat answer to the question raised by Donald Trump’s presidency. Also, given that I (Bales) bet on Trump to win $75,000 at 150-to-1 odds, I basically have to bet on Oprah now because of the #brand, but the market is still undervaluing unconventional candidates.

People Want to Vote for People They Don’t Dislike

President Trump still has his supporters, and he’s, like, really smart, but right now his approval rating is just 38.7 percent (per FiveThirtyEight). He endorsed Republican Roy Moore in the 2017 special election in Alabama for the Senate seat vacated by Jeff Sessions — even after Moore was accused by multiple women of sexual misconduct and assault over a period of years — and Moore lost to the Democratic candidate Doug Jones. Trump might have a hard time winning the general election anyway, and the public’s response to Moore last year and to Hillary Rodham Clinton the year prior suggests that people are actively choosing not to vote for candidates they dislike. Right now, 55.0 percent of all people polled disapprove of Trump.

People Like Oprah

This point seems obvious. People — all sorts of people — like Oprah. She’s real. She grew up poor and built herself into a mogul. She’s not an elitist: She was born in Mississippi, and raised in Milwaukee. Her first on-air opportunity was in Tennessee, and she built her media empire in Chicago, not New York or Los Angeles. She’s not famous for being in movies. She’s famous for being herself — and she’s the embodiment of the American Dream. Unlike many other celebrities, she has the ability to appeal to people all over the country.

If Oprah were to run, she’d probably have better voter turnout than HRC had — she’d almost certainly draw more people of color — and she’d also have a better chance of attracting moderate voters, especially women. If she runs, she has an underappreciated chance of winning both the Democratic nomination and the general election.

Oprah Might Actually Run

In the past Oprah has downplayed the possibility of running for president, but on Sunday night Oprah did this at the Golden Globes.

Freedman: I can’t watch that without crying.
Bales: I’ve never cried.

In the wake of Oprah’s speech, major media outlets have reported that Oprah’s close friends, confidants, and advisers are urging her to run in 2020 and that she is seriously considering it.

And why shouldn’t she?

The Democrats Need a Champion

Right now, the Democrats have no one who is a clear frontrunner. They have no one who has unified the party. This isn’t to say that they don’t have a number of people who could serve as perfectly respectable candidates, but they’re not particularly exciting. They all seem beatable — and the Dems want to win. There’s no clear candidate to keep Oprah from entering the race, and if she were to do so she would probably be welcomed as a potential savior by the left.

Are You Interested in a Freeroll?

As noted earlier, Oprah is +220 to win at BetDSI. She’s also -270 not to win. We typically don’t hedge, but there is an arbitrage opportunity here for people who want to limit their risk.

There might be yes/no props available at other books — as always do your research — but for the purposes of explanation let’s say that you could place the following bets.

  • $10 on Oprah to win in 2020 at +8,000 (MyBookie)
  • $27 on Oprah not to win in 2020 at -270 (BetDSI)

If Oprah were to win, you’d win $773 ($800 minus $27). If Oprah were not to win you’d win nothing ($10 minus $10). Again, evaluate all situations for yourself, but freerolling Oprah in 2020 . . .

. . . seems like a relatively non-donkey thing to do.

Photo Credit: Paul Drinkwater/NBC Handout via USA TODAY NETWORK

About the Author

Matthew Freedman is the Editor-in-Chief of FantasyLabs. The only edge he has in anything is his knowledge of '90s music.