Three Ways to Make Money Off of This Election

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Ever since I started writing this blog, I’ve needed a club to keep all the people away in the streets, at the grocery store, and even in the Arby’s drive-thru, who want to know how to make free money gambling on the election. Well, this is their day: I am tired of being interrupted every minute of my life, so here are my secrets. Make them count.

I am splitting the races that are worth your cash into three risk categories. It’s your call whether or not you want to be a hero. I personally like to be alpha AF, which is why I make my own jerky and crank power squats in a horse mask. But like I said, no one’s making you be a hero.

Before you go on, make an account on PredictIt.Org and check out my post WTF Is Political Gambling?

Now that you’ve done that, it’s time to party. From easiest to hardest, here we go.


charlie sheen ted cruz

The only people not making bets in this division are boneheads. These races require zero brainpower, which I know because I usually bet on them after huffing glue or watching a Zac Efron movie, which is basically the same thing. All you need to know is whether or not the political party that should win a race, will win a race, and if the odds are good enough to risk some dough. They are, so make these bets today:

Will Ted Cruz Be Re-Elected? – YES – 82 cents

Which Party Will Win the TN Senate Race? – YES on GOP – 81 cents

Will Heidi Heitkamp Be Re-Elected? – NO – 87 cents.

Will Tina Smith Be Re-Elected In MN? – YES – 84 Cents

Full analysis on select races here: TX, TN, ND.



So you laid out some bets on our gimme Senate races and you still feel like a beta? I can’t really blame you, because there are more balls in a Pumpkin Spice Latte than a bet that the Republicans can win in Tennessee, Texas, and North Dakota; and that a Democrat can hold Al Franken’s old Senate seat.

If you want to get your stones back, I have three quick options for you: (1) start dressing like Patrick Swayze in Road House; (2) get into a bar fight with a professional bullrider; or, (3) up your risk profile and get into the Repeal and Replace markets.

If you want to crush at this level, you’re going to have to put on your thinking cap. The secret to doing this is to pretend like you are Anderson Cooper or Joe Scarborough and just continually repeat lines like, “Blue Wave,” “suburban voters” and “changing demographics” and hope that you are making sense. If you do this for long enough, someone will probably offer you a TV show. But on the off chance that they don’t, you’ll at least know what the basic trends of this election are:

(1) Suburban women and educated, high-income voters don’t like President Trump and are frothing at the mouth to vote against him;

(2) Minorities aren’t feeling Republicans but they might not be feeling voting either;

(3) Men, rural, and working class voters are suddenly engaged and leaning Right… but will their excitement last into November?;

(4) Historic regional political cultures are often in conflict with #1-3.

I am looking for races that only test 1-2 trends at a time. Anything more than that is a giant political pretzel and I don’t fuck with those. So here we go:

Examples of Good Mid-Risk Markets:

Rep. Mimi Walters (R) in Orange County (#1 & 2 vs. #4). A Republican running for re-election in a historically conservative district. However, it’s an educated, suburban region that is heavily influenced by changing demographics and the PC Church’s jihad against Trump. I am betting the trend here. Bye-bye, Rep. Walters.

Which Party Will Win CA-45? – YES on Democrats – 67 cents

Will Mimi Walters Be Re-Elected in CA-45? – NO – 67 cents


Rep. Peter Roskam (R) in the Chicago Suburbs- (#1 vs. #4). What can I say, Peter Roskam is basically in a Republican bear trap. His generally conservative district also happens to be the kind of place where every house has a Volvo station wagon, a Kenyon degree, and a mom who covers her kids’ ears whenever Donald Trump talks about banging hookers like Stormy Daniels. Also, FYI, his opponent might be the biggest troll in this whole election.

Will Peter Roskam Be Re-Elected? – NO – 59 cents

roskam mkt

For a similar race with less risk, check out Kevin Yoder’s re-election in KS-03.

Rep. Mike Bost in Southern Illinois – (#3 vs. #1). This race is in the opposite part of Illinois and will result in the opposite outcome: a Republican incumbent who will hold his seat.

bost mkt

Which Party Will Win IL-12? – YES on GOP – Anything under 80 cents


Drive to the grocery store and buy some sunscreen because this is the real blast furnace of democracy. I personally try not to even think about these races after 6:00 PM, because if I do, I will wet the bed. This is because the Trump-Pence Brexit Division is full of races that are either: (1) absolute horror shows of conflicting trends; or (2) bets against common sense.


The Trump-Brexits are where you can still get some strong odds, but it is full of bears that will rip your face off. Here are some of my favorite examples:

“Texas is a rock-solid Red state. Also, Republicans are going to get de-balled by female voters and educated people in the suburbs.”

So WTF is going to happen in the suburbs of Houston and Dallas, where Obama got smoked like a side of brisket, but Hillary won in 2016?

john cena mind blown GIF

If you want to play that mean game of slots, check out Rep. Pete Sessions and Rep. John Culberson’s races. I’m invested in Sessions with a YES at 63 cents and it is costing me sleep. If Pete Sessions doesn’t hold, I will be crying like John Boehner at his grandkids’ Christmas Pageant for most of 2019.

boehner cry 1

“Changing Demographics and Trump’s negative racial attitudes are pushing Orange County, a longtime GOP stronghold, into the Democratic Party’s hands.”

You believe that? Then look at Young Kim and Gil Cisernos’s race in CA-39. This one is a savage mindfuck to California’s PC Church because it is asking voters to choose between two protected classes: a liberal, Hispanic, male (Cisernos); and a conservative, Asian, woman (Kim), in a majority-minority district that rates as an even split between Rs and Ds. What a disaster. I will honestly be surprised if this race doesn’t result in at least four yoga cult-suicides as woke Californian’s deal with the trauma of choosing between their PC religion and their politics.

ca-39 fire

“Rural House seats in Trump states are going to be the bulwark against the Blue Wave.”

Not so fast, hombre. Have you looked at Andy Barr and Amy McGrath’s race in KY-6? What about J.D. Scholten and Richard Ojeda? What about every seat in Upstate New York? All of these races feature some truly savage Democratic contenders who have never even heard of SoulCycle and will punch you in the face if you serve them kale. I personally think that there is trouble in GOP paradise, or whatever it is you call a corn field full of people who shop at Walmart.

“Brett Kavanaugh’s confirmation crushed the Democratic Party’s hopes of picking up or holding Senate seats in rural states.”

Hmmm. Probably, but no one is talking about the Mississippi special election where there is almost no polling, and a GOP candidate who is less exciting than the Magnum P.I. reboot.

Also included in this bracket is Sen. John Tester’s (D-MT) re-election (much safer).

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As well as Senator Claire McCaskill’s (D-MO) re-election in Missouri, where literally no one has any clue what is going on. Equally savage is the cage match currently happening between Sen. Dean Heller (R-NV) and Rep. Jacky Rosen (D-NV).

And then, finally, the crown jewel of all the Senate mind-erasers…

Will Rep. Martha McSally (R) or Rep. Kyrsten Sinema (D) win Jeff Flake’s AZ Senate Seat? Honestly, the last time I saw this type of quality matchup, it was between Batman and Mr. Freeze in the absolute classic, Batman and Robin. Unfortunately, this masterpiece was way ahead of its time and sunk the Batman franchise for eight years while the world played catchup, which is why I am extremely concerned about the implications of this Arizona Senate race. It could be global.

I have a bet on Martha McSally winning but I’ve been slamming more Maalox than Natties since I made it. No bueno, padre. Check out our full analysis of the race here.


Once you’ve made your picks, you can go over to PredictIt’s total seats market and wager on exactly how many House and Senate seats each party will have, as well as their leadership for the next Congress. The odds on this are pretty strong, but the best plan I’ve got to nail the answer is to train monkeys to throw darts at the wall and then ask Jane Goodall to interpret the results. I’ll be sure to post back once she does (for real, I will tho.)

Now go out there and make some free money.


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***I am not a financial advisor. This is not financial advice.***

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