Betting on the Oscars: A Follow-Up Conversation
“This might be one of the most straightforward Oscar races in recent history.”
Last month I talked to my friend Jason (last name withheld for privacy reasons), a management consultant who has never lost money in his seven years of betting on the Academy Awards. We spoke about his investment-based approach, early picks, and how prediction markets like Kalshi and Polymarkt differ from traditional sportsbooks. It got a lot of traction thanks to Official Substack excerpting it in their weekly roundup, and it’s still worth a read if you haven’t gotten to it:
That interview took place in early January, after the Golden Globes but before the actual nominations were announced. In U.S. political terms, this was after the Iowa caucuses but well before Super Tuesday. Now that the primaries are over and we’re in the final phase of this Hollywood election, it’s a good time for a follow-up conversation. We took stock of how his initial bets have panned out, the juicy category he’s thinking of jumping into, and whether or not you should bet on a tie happening.
Paid subscribers get full access to his updated analysis, as a treat:
The 98th Academy Awards ceremony takes place on March 15. This is three weeks from now. Jeez.
Another Interview With the Gambler
This interview, which has been edited and condensed, was conducted on February 19, nearly a month after Oscar nominations were announced and the Director’s Guild handed out their awards. The two biggest precursor awards, the British Academy and the Screen Actor’s Guild, have yet to be handed out. After that, the odds will solidify.
How’ve you been, Jason? It’s been over a month since I saw you.
I’ve had crazy work travel. I was in London for a week. The week after that I was in San Francisco. The week after that I was in Poland and London. And I was back in San Francisco last week. Next week I’m going to Chicago and then San Francisco.
The life of a consultant, I suppose. A lot has happened in the Oscars landscape since our first interview, particularly now that the nominees have been unveiled. Has anything changed?
A lot has happened, but I don’t know if a lot has changed. I think this might be one of the most straightforward Oscar races in recent history. I’m eager to check the historical odds to see if this is true1. Across the board things have solidified toward favorites in a way that is unusual.
Even in categories where maybe when we talked a month ago it was a little bit more of a coin flip, it’s gone toward a favorite, and in some cases a heavy favorite.
How do you feel about your picks overall?
I feel pretty good, better than I did last year. But the odds aren’t as good so I’m not putting as much money down. It was a fraction of what I put down last year. But I look forward to being surprised.
Just to recap, what bets did you place in January?
I bet on eight categories. All my positions have improved, with one giant exception.
One Battle After Another for Picture—the odds strangely got worse so I doubled down this week, we’ll talk about that. I also bet on this for Editing.
Chalamet for Best Actor. KPop Demon Hunters for Song.
Sinners for Original Screenplay—that one’s moved well. Paul Thomas Anderson for Director—that one’s also moved well.
F1 for Sound, I got in at 40%. It’s at 80% now.
And then International Feature Film—we don’t have to talk about it—
You called it for It Was Just an Accident.
We’re gonna start with my miss? We’re not going to start with my seven hits?
It is dead2. I’m still a little befuddled by it, to be honest. I think they completely botched the For Your Consideration campaign.
I think the healthy lesson is this: under no circumstance do you put money down on this category until the nominations come out.
Did you sell3?
No. It’s so low that it’s not really even worth selling. At this point I’m holding on for the chance that there is a late push. I’ve just written it off in my mind.
I’m not sweating it too much because the two picks that I really liked were It Was Just an Accident for International Feature, which was trading around 40%, and then F1 for Sound, which was also trading around there. And that one is like 80-something now. That should more than pay for the International Feature bust. In my head, they cancel out.
What percentage of your portfolio was on International?
About 10%. I really liked this bet. The only reason I didn’t put more money into it was because Kalshi wouldn’t let me without changing the odds.
Besides that one exception, you sound pretty happy with holding on to your current bets. Is there anywhere that you’re doubling down and putting in more money at this stage of the game?
I thought One Battle After Another was a lock for Best Picture. Somehow the odds have gone down. It was 82% on Kalshi when we talked a month ago. It is now 74%. That is the only bet where I doubled down so far. I put in the equivalent of 15% of my original portfolio.
I think what’s happening here is a lot of casual betting. Second highest odds is Sinners. I think that might be a reaction to that film setting the record for nominations. That is a gigantic trap. And then third place is Hamnet at 9%, which is 9% too high.
I actually did the math on this. If you had $90,000—which is the maximum that you’re allowed to bet on this category right now—and you just put it on “no” on Hamnet, you would make more than you would get from a high-yield savings account. So if you’re thinking about putting money in your high-yield savings account, just put it on Hamnet to lose the Best Picture Oscar.
A part of me hopes this take ages really badly and Hamnet somehow wins.
I think the readers who follow your advice will doxx you. So we should do a quick disclaimer: none of this interview should be construed as investment, betting, or financial advice. This is purely for entertainment value. You are responsible for whatever decisions you make.
[sarcastically] And Kalshi is not a gambling platform.
One thing we didn’t get to talk about last time was portfolio allocation. How do you decide how much money you’re actually putting in, both as a whole and splitting across each category?
Hopefully you don’t have enough money in this that you actually have to worry about adjusting risk and stuff. It’s not like a stock portfolio. We talked about this a little bit last time. It depends why you’re in it. Are you looking for the thrill? Are you looking to make some money? How much money do you need to be happy?
With me, I’ll put money down on the things I generally like to see win anyway. If I make a meager sum, I’m pretty good with that. I’m not going to go crazy or anything. With that in mind, I do care about balancing. I look at the adjusted odds of the things I have. That lets me go a little riskier and maybe play in some categories I wouldn’t have played in in a vacuum. That tends to mean putting a lot more money into the popular categories.
I’m starting to wonder if, in this new age of Oscars betting being open to everyone, the most popular categories are getting more populated with casual bettors.
That’s a really good point: where more people are betting, you’re getting people who are less informed.
And that’s the whole reason I even do this. It’s not sports, where you have really sophisticated bettors using algorithms and stuff. I’m still taking advantage of some market inefficiencies.
Are there any categories you haven’t bet on yet but are a potential opportunity?
There is one, Sinners in Cinematography. I haven’t decided yet whether or not to go in. It’s low odds but good value, if that makes sense. I’m thinking, “How much fun do I want to have?”
About a month ago it was a three-horse race between One Battle After Another, Sinners, Train Dreams. One Battle After Another has kind of gone to the slight favorite. It’s around 52% right now. We talked a lot last time about my downballot theory that it is a One Battle After Another year, so that would make sense.
But if you look at odds over time, it gets a little bit suspicious. A month ago, Sinners was around 40%. At one point it became the heavy favorite at 60% but it’s gone down by half. That shift towards One Battle came after the Director’s Guild Awards went to Paul Thomas Anderson. But best directing is not best cinematography.
And there’s a great storyline around the cinematographer of Sinners. She’d be the first woman ever to win. I don’t think that on its own is a good enough reason to award or bet, but combined with the craft itself—“Hey, this might actually just be the best-shot movie of the year”—you could talk your way into it.
It’s at 30% and that is probably a little too low. It should be 50%. So I think if you were brave—or bored, which I kind of am—you might go in on Sinners. But I haven’t put any money down yet. If the odds go down more, I’m going to get really tempted.
You usually make bets three different times—January, early February, and then a week before the Oscars. Are you planning to do that last minute betting round again?
I’m keeping an eye on Editing. The first thing I look for is doubling down—categories that I liked before and liked enough to get into. It’s a bit of a self-fulfilling prophecy. The things that I like are probably going to be the things that I’m already in on.
Other than that, I just track the odds across the board. See if any of them change in a way that I disagree with or that I think are interesting. But I don’t think that’s going to happen this year.
I was expecting to put more down last week. I was ready to, and then I just couldn’t find the bets, besides doubling down on Best Picture. That’s why I’m a little shy on going in for cinematography, because I’m thinking, man, am I just bored?
Would anything change your position on Timothée Chalamet? We talked about him a lot last time around.
Michael B. Jordan winning a SAG award would change a lot of things. But he’s like the third person now that we’re saying could upset Timothée. A month ago, we weren’t even talking about him. We were talking about Leo.
I think short of Kendall Jenner—is it Kendall or Kylie? I always mix them up. Whichever one he’s dating, short of her doing something crazy like starring in a Coke commercial where she solves racism, I don’t see Timothée not getting it4.
Kalshi lets you bet on a tie—not which two films tie, just a tie in general. Would you recommend this?
I wish I had a clever, thoughtful answer other than no, don’t do it. I just looked it up: it’s happened six times in the history of the Oscars. I’m surprised it’s happened that often.
What if I just want to put 10 bucks on a tie in every category, just to see what happens?
You would lose all your money.
Final question. I’m pretty sure Kalshi will put up prop bets closer to the ceremony, like how long the telecast will be, or what Conan O’Brien will say in his monologue. What prop bet would you feel comfortable putting money on?
Number of times ICE is mentioned. I think there’s a sweet spot between three and ten.
You have a more optimistic viewpoint on Hollywood getting controversial than I do.
I am also considering the non-proper noun “ice.” Just cold.
Doesn’t count.
It’s not a real category anyways.
Thanks again, Jason, for chatting with me and sharing your wealth of knowledge.
It was a very long way of saying not much has changed.
You can see historical Oscars betting odds here, if you want to compare to this year’s odds. (Use “Sports Fan” mode to see +/- odds)
It Was Just an Accident was nominated in International Feature but not for Best Picture. A Best Picture nominee has never lost to a non–Best Picture nominee in this category, so unless this precedent is broken, it will be Sentimental Value or The Secret Agent.
Prediction markets, unlike traditional sportsbooks, let you sell your position. It’s similar to stock trading.
Timothée Chalamet is dating Kylie. Kendall was the one who did that Pepsi ad.