Along with 65,844,954 others, Dennis woke up on the morning of November 9, 2016, with a pit in his stomach. But Dennis felt more than the shock that rattled his faith in the country — he felt the loss in his wallet.
“It might be one of the worst bets of my entire life,” the 33-year-old Chicagoan tells me. Which is saying something, because Dennis is nothing short of a habitual gambler. He bets on NBA drafts; he’s participated in a “fantasy crime league” that places odds on NFL players getting arrested in the offseason; and he even won $50 after correctly betting on Pope Francis.
And back in 2016, just like Nate Silver and every other notable pollster-stathead, Dennis was confident Hillary Clinton would win the presidency. “The money line was –265,” he explains, meaning he’d have to bet $250 to win $100. “I’d waited for her odds to dip a little, and her health scare was the opportunity in September. At that point, I was very confident in her winning; I even told some degenerate friends about the number coming down. It just looked like a lock, so I put down the most money I’ve ever placed on a single event, about $1,200.”
On election night, Dennis sat in a bar watching the coverage. “I even had some maps drawn out,” he says. “In the worst-case scenario, I had Clinton winning narrowly 271 to 267. But I never imagined she’d lose Wisconsin and Michigan. That was the killer.”
It was enough of a killer, in fact, that he took a break from political betting during the 2018 midterms. But he jumped back into the fray to bet $25 on Kamala Harris after a “good showing” at the first Democratic debate. Harris, though, dropped out of the race in early December, and now Dennis needs to make his money back.
Primary season has turned into a different kind of football season. Dennis chases any Saturday losses on Sunday and any Sunday losses on Monday night (rinse and repeat). Except instead of betting on teams and games, he’s rolling wins and losses into candidates and states.
What exactly, though, is his strategy? Or the strategy of any kind of political bettor? For answers, I turned to him and a couple of other guys who throw money down on election season as though it’s the Super Bowl.
Dennis, 33, Chicago
Money is just money, and losing it is a part of gambling, right? There’s also always a fear of missing out that drags you back in, so I made two small wagers on the president elect for 2020.
After the first debate, I thought Kamala might get to the final four or so in the nomination race. Plus, 10 to 1 to be president-elect provided good enough value in my head. The other bet, who I’m not going to name so as not to jinx them, is 35 to 1 to be president-elect. They likely won’t get the Democratic nod, but I placed it recently to root for someone after Kamala dropped out. I also have a wager from 2018 with a friend that Trump wouldn’t win re-election at even odds.
I’m not super sure how they set the odds. Maybe it’s off polls, public perception and current liabilities. But like in sports, many successful bettors wager on the numbers, they don’t bet on the team. So political bettors shouldn’t care about red versus blue. It’s about that green.
Kyle, 25, Michigan
The election cycle is historically very much a marathon, not a sprint, which makes me hesitate to call election odds volatile. On the other hand, it seems like we’re in uncharted waters, and the odds reflect that. In the past month, my book’s odds have moved Pete Buttigieg from a virtual tie with Biden to a +2,800 long shot to win the general election, the same odds as Andrew Yang. Elizabeth Warren’s have fluctuated pretty wildly, too.
The question of betting before or after Iowa is about whether you want to maximize earning potential (before) or minimize risk (after), since the caucus has historically played a huge role in who becomes the nominee. For me, we’re still too far out to be worth the risk. Candidates are still dropping out, seemingly out of nowhere, so it’d just be throwing away money to bet on someone who may never even be on the same debate stage as Trump.
Still, set aside the fact that I’m a Bernie Sanders supporter, I can’t ignore the fact that he’s gone from +800 to +350 in the last month, giving him the most favorable odds amongst the Democratic candidates days before Iowa. So maybe I’ll put some money on Bernie soon, since I can only imagine his odds will continue to fall.
No matter who the Democratic candidate is, I suspect Trump will be the favorite for most, if not all, of the lead-up to the general election. Which is a third option — a common “strategy” in sports gambling and politics gambling — to bet against your own team or “interests.” So I could bet against Bernie and put myself in a hypothetical win-win situation — either Bernie wins, or I win the bet. But I also think Trump will stay right around the -125 money line, which, for me, isn’t worth tying up money for nine months to bet on him now.
Brian, 34, Connecticut
My worst bet actually just happened on articles of impeachment. My position was three [articles] to be sent instead of the two that were sent by the House. The way I saw it, they had an opportunity to allow for more wrongdoings to be discussed openly for all to see. I don’t think anyone thought these had a chance in the Senate, but I was surprised they didn’t go more aggressively without being overbearing. By the time two had been sent over, the market had adjusted and stuck me with a ton of worthless shares. I am, though, still holding the position because it doesn’t close until 3/31, and I still think the opportunity is there for Congress to start the process over again.
The site I bet on works more like a stock market than betting against a house. Once it’s over, whomever wins would be at $1 flat per share. So say you bought Bernie stock at .63, you make 37 cents per share. If you have 100s of shares, it ends up being a lot of money. This is a much more fluid deal, not an all-or-nothing one. I sell when someone is high and I buy low, not necessarily who’s going to outright win.
I’m a momentum bettor, and politics is all momentum. I will ride waves of candidates. I bought positions in Warren before the first debate because I knew she was a good speaker so it was easy to see her moving up positions. I’ve since sold those positions. I think Iowa will change the odds a ton, especially for the bottom group. People like to vote for a winner, and the betting world will adjust accordingly. In particular, things are really going to swing for Yang, Mayor Pete and Amy Klobuchar. Meanwhile, Bernie could cement that he’s the frontrunner with a win here, especially after losing in 2016.
I also do some goofy bets to have fun, because it has less to do with serious issues that I care about on a personal level. Like if Donald Trump Jr. will go to jail or how many times Trump will tweet over the course of a week. You can usually kinda get a pattern of how he’s doing in that regard halfway through a week, especially if he seems to be on a golf spree. You can also make the quickest money this way if he goes on a retweet/tweet spree right before a deadline.
Overall, I try not to let my prejudices get in the way. But like everything, they’re hard to separate — especially on something that has good value, too.