Big Take: Taylor Swift Wedding Predictions Are the Hottest New Trade

Summary

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Podcast Summary: Odd Lots – Big Take: Taylor Swift Wedding Predictions Are the Hottest New Trade

Date: August 31, 2025
Host: Sarah Holder (Bloomberg)
Guests: Francesca Maglione (Bloomberg Personal Finance Reporter), Annie Massa (Bloomberg Wealth Reporter)
Main Theme:
Exploration of the booming world of online prediction markets, with a focus on the surge in bets placed on the future of Taylor Swift and Travis Kelce’s relationship—specifically, their recent engagement, and how these platforms mix pop culture, finance, and real-world consequences.

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Episode Overview

This episode investigates the rise and ramifications of online prediction markets like Polymarket and Kalshi, using the frenzy around Taylor Swift and Travis Kelce's engagement as a lens. The panel discusses how betting on celebrity events has become a cultural and financial phenomenon, the mechanics of these platforms, their growing legitimacy and valuation, regulatory challenges, ethical controversies, and the potential for these markets to influence both culture and real-world events.

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Key Discussion Points & Insights

1. The Swift-Kelce Engagement as a Betting Sensation

• Host Sarah Holder starts by examining reactions to Swift and Kelce’s engagement and how it’s become fertile ground for online bets.
• [01:54] Sarah introduces Francesca and Annie as not extreme Swifties, but close observers of the trend.
• "So many group chats this week I found myself talking with my coworkers about Taylor Swift." – Sarah Holder, 01:43
• Prediction markets lit up after the engagement, with rapid growth in bets about a wedding date and relationship milestones.
• [03:16] “Within hours of Taylor and Travis’s announcement, gamblers on Kalshi had placed about $80,000 worth of bets on the couple’s wedding timeline. And by Thursday, that number had doubled to around $160,000.” – Sarah Holder
• By Thursday afternoon, the odds of a Swift-Kelce wedding by year-end settled at only 7%.

2. How Prediction Markets Work

• [04:29] Annie breaks down how market mechanics mirror sports betting, but the scope is broader—almost anything, from elections to album drops (e.g., “Will Taylor Swift release an album by the end of the year?”).
• Real-time odds update as participants place bets for “yes” or “no;” small wagers can lead to significant payouts when an event settles.
• "You bet a few cents on a yes or no and the market settles to a dollar… if you were correct, then that market settles to a dollar.” – Annie Massa, 05:55

3. Explosion of Online Betting on Pop Culture & Current Events

• [05:29] Polymarket, founded in 2020, has millions in backing from Peter Thiel and Vitalik Buterin, and claims $16 billion in bets placed by 230,000 monthly users.
• "When it comes to Taylor Swift in general, I think people are betting on things...Like, when are they gonna get engaged? Is the wedding gonna happen this year? Anything you could think of, people are betting on. There's a market for that, for sure.” – Francesca Maglione, 05:29
• The cultural crossover into “gut check” territory: people reference prediction market odds to validate their own opinions on a range of topics.

4. Funding, Backers, and Market Valuations

• [07:18] Kalshi is now valued at $2 billion; Polymarket at $1 billion—powered by investments from Silicon Valley (e.g., Founders Fund) and legacy Wall Street (Susquehanna).
• "Both Kalshi and Polymarket have been fundraising and Kalshi is valued at $2 billion now. Polymarket’s valued at about a billion dollars now.” – Annie Massa, 07:18
• Donald Trump Jr. has advisory roles at both firms and investments via 1789 Capital, adding political weight and notoriety.
• Trump Jr.’s rationale includes prediction markets outperforming traditional polls and offering commercial opportunity.

5. Regulatory Hurdles and Government Scrutiny

• [12:27] The Commodity Futures Trading Commission (CFTC) oversees the derivatives market, generating friction with online betting platforms.
• "The CFTC has taken a pretty stern approach in the past toward these contracts...and basically said if you’re betting yes or no on the outcomes, if you have money on the line, that type of product is something that we regulate.” – Annie Massa, 12:55
• CFTC targeted Kalshi in 2023 for political betting; litigation ensued and the CFTC ultimately dropped its appeal.
• Polymarket faced both CFTC and DOJ scrutiny, an FBI raid, and a million-dollar fine. The US even banned Polymarket for domestic users, but the site continued to feature U.S.-centric markets globally.
• [14:52] In July, Polymarket found a path forward by acquiring a regulated exchange, ending US probes and granting the platform US legitimacy.

6. Cultural, Political, and Ethical Implications

• Prediction markets are becoming a tool for “wisdom of the crowds,” but ethical questions persist—e.g., betting on disasters or morally gray outcomes.
• [16:01] "Earlier in the year when there were wildfires in Los Angeles, Polymarket had a market on the trajectory of the wildfires, which people found pretty untoward. So it can go all over the place. It’s not just in the realm of politics or even pop culture. You can put odds on a lot of different things.” – Annie Massa
• Potential for negative influence: creation of betting markets can encourage undesirable behavior (like incentivizing disruptive activities at WNBA games).
• Demographics matter—most participants now are men (“crypto bro” archetype), but a shift to broader participation could affect market accuracy and outcomes.
• “Right now, mostly men are users. Maybe we see more women go on there and it become more popular because...maybe more accurate in that way as well.” – Francesca Maglione, 16:21

7. Prediction Markets' Influence on Public Perception and Events

• The panel discusses how the existence of these markets, and their published odds, can sway societal behavior or even outcomes (akin to poll effects on elections).
• “There are impacts of seeing where the wisdom of the crowd is pointing out.” – Sarah Holder, 17:28
• If public sentiment in prediction markets is biased or skewed, it can propagate misperceptions and change how people—and perhaps even participants in the events themselves—act.
• “...That's dangerous in the sense that one opinion is getting kind of an advantage over another as more people kind of turn to Kalshi or Polymarket...If you're gut checking against kind of a biased opinion, then that might influence real life events or the way that people think about races or things.” – Francesca Maglione, 17:05

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Notable Quotes & Memorable Moments

• [03:37] “We had like a bet on our team and people had to give their like what they thought was going to happen with them in 2025 and I had said that they were going to break up, so I don't think I was expecting that at all.” – Francesca Maglione
• [04:39] “You can watch in real time as these odds change based on who's placing bets for yes, no, or a range of other different outcomes depending on the type of market.” – Annie Massa
• [16:01] “It’s not just in the realm of politics or even pop culture. You can put odds on a lot of different things now.” – Annie Massa
• [17:43] "People want to win. And so if you think that an outcome is going to go a certain way because you saw it on Kelshi, then maybe that will make you go that way as well." – Francesca Maglione
• [17:52] “Well, we’ve got to hope that Taylor was not influenced to get engaged by Polymarket. I’m sure there’s more love there.” – Sarah Holder

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Key Segment Timestamps

• 01:39 – Introductions; Taylor Swift “Swiftie” status
• 02:18 – The engagement and its ripple effects in prediction markets
• 03:08 – Trading volume; growth of prediction betting
• 04:29 – Mechanics of prediction markets vs. sports betting
• 05:29 – The inception and evolution of Polymarket
• 07:18 – Valuation, funding, and investor landscape
• 08:36 – Donald Trump Jr.'s involvement and rationale
• 09:36 – Ethical implications and regulatory controversy
• 12:27 – The CFTC crackdown and subsequent litigations
• 14:52 – Pathways for Polymarket to become US compliant
• 15:23 – Future influence and cultural reach of prediction markets
• 16:21 – Demographic trends and potential for mainstream adoption
• 17:05 – Concerns over market bias influencing real events

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Conclusion

The episode uses Taylor Swift and Travis Kelce's engagement to spotlight the exponential rise of prediction markets as both financial instruments and cultural barometers. The conversation covers everything from technical mechanics and investment narratives to regulatory intrigue, shifting demographics, and the increasingly blurred line between entertainment and finance. The hosts leave listeners pondering the real-world impact and ethical boundaries of turning current events—and even personal milestones—into high-stakes bets.

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Transcript

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[News Announcer]

News.

[Sarah Holder]

Would you consider yourself a Swiftie?

[Francesca Maglione]

I think it's a scale like oh.

[Sarah Holder]

So many group chats this week I found myself talking with my coworkers about Taylor Swift.

[Francesca Maglione]

I like her music but I'm not like keeping up with every single thing she does with her life.

[Sarah Holder]

That's Bloomberg's personal finance reporter Francesca Maglione.

[Annie Massa]

I am a big fan and that's.

[Sarah Holder]

Annie Massa, a Bloomberg wealth reporter.

[Annie Massa]

I am probably not all the way down the rabbit hole on every single development and every single Easter egg and every single song, but was I singing August in honor of my friend's birthday at a karaoke bar last week? Yes.

[Sarah Holder]

Taylor Swift and NFL player Travis Kelce announced their engagement on Tuesday and I wanted to talk to Francesca and Annie because there's one corner of the universe that's been turning their engagement into a money making event. The people making predict financial bets on where their relationship will go next.

[Francesca Maglione]

We had like a bet on our team and people had to give their like what they thought was going to happen with them in 2025 and I had said that they were going to break up, so I don't think I was expecting that at all.

[Sarah Holder]

Did you lose money on that bet?

[Francesca Maglione]

No, no. No money was involved, thankfully.

[Sarah Holder]

The rise of legal online betting in the US over the last few years has ushered in all kinds of bets, like bets on current events and pop culture made on prediction markets like polymarket and Kalshi.

[Francesca Maglione]

So far this year, both of these platforms have had more than a billion in trading volume. So they've become more significant as the years go by.

[Sarah Holder]

Within hours of Taylor and Travis's announcement, gamblers on Kalshi had placed about $80,000 worth of bets on the couple's wedding timeline. And by Thursday, that number had doubled to around $160,000. By Thursday afternoon, the odds of Taylor and Travis getting married by the end of the year hovered at around 7%.

[Annie Massa]

I was not placing any bets personally, but I was kind of bearish. So here we are. And very happy for them, obviously.

[Sarah Holder]

Yeah, bullish. Now on Travis and Taylor, 100%. I'm Sarah Holder and this is the big take from Bloomberg News today on the show how prediction markets work, why they're exploding in popularity, and what this all means for the people and events they're betting on. Betting isn't new. Humans have been doing it for millennia. But online prediction markets like Polymarket and Kalshi have recently surged in popularity in the US If I've never used Polymarket before or Kalshi, is this like sports betting or is it different? How does it actually work?

[Annie Massa]

The easiest explanation would be in the context of a presidential election, who will win? Kamala Harris or Donald Trump?

[Sarah Holder]

That's Bloomberg wealth reporter Annie Massa.

[Annie Massa]

And you can bet on who will win, but now you're able to get odds effectively on all sorts of other different things. So will this event happen in the future, yes or no? Will Taylor Swift release an album by the end of the year, yes or.

[Sarah Holder]

No, and the odds of that went up significantly?

[Annie Massa]

Yes, exactly. And you can watch in real time as these odds change based on who's placing bets for yes, no, or a range of other different outcomes depending on the type of market it is.

[Sarah Holder]

Polymarket was founded in 2020 and it's gotten major funding support from Peter Thiel and Ethereum founder Vitalik Buterin. This year alone, its nearly 230,000 monthly users have placed nearly $16 billion of bets on real world events. Here's Francesca Maglion, Bloomberg's personal finance reporter.

[Francesca Maglione]

It kind of started around the presidential election and it's kind of shifted just beyond politics and everything in pop culture. When it comes to Taylor Swift in general, I think people are betting on things as is she gonna have a baby this year? Like, when are they gonna get engaged? Is the wedding gonna happen this year? Like anything you could think of, people are betting on. There's a market for that, for sure.

[Sarah Holder]

And what happens when you win and what happens when you lose? Like how much money is on the line here?

[Annie Massa]

These markets have grown in size over time, but a basic example would be you bet a few cents on a yes or no and the market settles to a dollar. And so effectively, you've put down a few cents to place the bet based on what the odds are. And if you were correct, then that market settles to a dollar.

[Sarah Holder]

This can all happen quickly. You type in your card info or hook up your crypto wallet and put some money on the odds of the Yankees winning to or on Travis and Taylor tying the knot by the end of the year, Depending on what you're wagering on. The market closes when an event ends, like after the last inning in a baseball game. Or it could end at a preset cutoff time. And once the market closes, you either get your payout or you lose.

[Francesca Maglione]

There's been some studies that have said that Americans are taking money out of their brokerage accounts to fund some of these wagers. And in extreme cases, there's losses from gambling that can contribute to auto loan delinquencies and bankruptcies.

[Sarah Holder]

Is this part of a broader trend of online betting markets gaining popularity like DraftKings or other websites?

[Francesca Maglione]

Yeah, sports betting we've seen grow in popularity. And it's also interesting just culturally now people will go online to check what are the odds of this happening. So it's becoming kind of a cultural phenomenon or a place that people go to gut check anything that they're questioning or thinking about.

[Sarah Holder]

What is a company like this worth?

[Annie Massa]

So actually, both Kalsheet and Polymarket have been fundraising and Kalshi is valued at $2 billion now. Polymarket's valued at about a billion dollars now. The other thing is the intersection of the types of investors in these companies. You have an intersection of Silicon Valley and some more traditional Wall street kind of firms. So Susquehanna, which is not maybe well known on Main street, but very well known big Wall street trading firm, is a big backer of Kalshi. So again, like a mix of both the more Silicon Valley side of things and the Wall street side of things. And Founders Fund is a big backer.

[Sarah Holder]

Of Polymarket and Some other notable backers like Donald Trump Jr. Donald Trump Jr.

[Annie Massa]

Has been taking on advisory roles at a whole bunch of different companies. That's included cryptocurrency realm, it's included firearms, all kinds of different companies. But he now has a pretty strong foothold in both major prediction markets in the US In January, became an advisor to Kalshi and just became an advisor to polymarket. And he is a partner at this firm called 1789 Capital, which invested in polymarket.

[Sarah Holder]

Why is he so interested in this company?

[Annie Massa]

He said when he took the role at Kalshi that prediction markets allowed him and his family when they were watching the returns for the 2024 election at Mar a Lago to kind of have a better finger on the pulse of what was actually going to happen versus polls. Another thing that advocates of prediction markets say is that they're usually more accurate than polls, which you can debate, but that's what advocates say. And so he took the approach that, oh, you know, Kalshee helped my family understand what was really going on. It's also very possible that he sees a lucrative business opportunity in advising both of these companies. Who's to say? And so what's really happened is in the past year, and especially under the Trump administration, you've seen a more lax regulatory approach to policing some of these prediction markets which have been very controversial over time.

[Sarah Holder]

Controversial not only because of that murky regulatory landscape, but because of the real world implications of betting on real world events.

[Annie Massa]

You can look at it two ways. If you are an advocate for prediction markets, you might say, well, this is providing some kind of valuable information or wisdom of the crowds on anything that will happen next. Even if a situation is tragic. If you're a detractor, you might say, well, you can come up with all kinds of twisted markets or sick markets on things. And is, is that really a good idea to start putting that out for people to win money on?

[Sarah Holder]

Yeah, it's a really thorny ethical question.

[Annie Massa]

Yeah.

[Sarah Holder]

Prediction markets, rocky road to regulation and how they're influencing the way we think about and experience current events. That's after the break.

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[Sarah Holder]

A few years after prediction markets hit the scene, the industry faced a major roadblock. People were flocking to sites like Polymarket and Kalshi, but the platforms were operating in a regulatory gray area, and Bloomberg reporter Annie Massa says they drew the attention of the Commodity Futures Trading Commission or the cftc. It's a federal agency that regulates the derivatives market, which, unlike traditional gambling, is not regulated by the states.

[Annie Massa]

The CFTC has taken a pretty stern approach in the past toward these contracts and basically said if you're betting yes or no on the outcomes, if you have money on the line, that type of product is something that we regulate and we oversee. You need to register with us and we are the watchdogs of this market. And both Kalshi and Polymarket have had their own skirmishes in the regulatory arena.

[Sarah Holder]

The CFTC first targeted Kalshi back in 2023. The regulator claimed that the political betting the platform facilitated was illegal and ordered them to stop operating. But Kalshee sued and after a federal court battle, the CFTC dropped its appeal in May of this year.

[Annie Massa]

But the tension for Polymarket had to do with two separate inquiries. There was a DOJ probe which resulted in this big FBI raid on the CEO's penthouse in Soho last year, and there was a separate inquiry from the cftc. The CFTC fined them over a million dollars, saying, you're allowing customers to bet on outcomes and trade contracts that are basically something that we should be regulating. You need to register with us.

[Sarah Holder]

In 2022, the US banned Polymarket outright. That meant US based users weren't allowed to place bets on the site.

[Annie Massa]

Polymarket was almost in exile in some ways just for the US that didn't.

[Sarah Holder]

Stop the site from featuring bets about the U.S. in 2024, Polymarket hosted millions of dollars in bets about whether or not Donald Trump would win the presidential election. Spoiler alert. He won, just as Polymarket users had predicted. I remember that with the presidential election that it was kind of like an informal poll that actually ended up being more accurate.

[Francesca Maglione]

Yeah, I have a friend that anytime something's going on, she just goes on Kalshee and is like, yeah, no, we don't have to worry about this. The odds were low or whatever the case might be.

[Sarah Holder]

Then in July of this year, the US government and Polymarket found a way to move forward. The US shut down the two federal probes opened under the Biden administration and Polymarket bought a derivatives exchange and clearinghouse called qcx, which gave them stronger legal standing to operate in the U.S. you both mentioned how influential Polymarket and Kalshi's predictions have grown as a cultural force, a political force. Where do you see that influence going next?

[Francesca Maglione]

I think in the future many people will turn to them to kind of gut check events or presidential races. They become really helpful to kind of see how people online are feeling.

[Annie Massa]

Like, will Lisa Cook actually be removed? Would be an example. There are some controversial ones. Earlier in the year when there were wildfires in Los Angeles, polymarket had a market on the trajectory of the wildfires, which people found pretty untoward. So it can go all over the place. It's not just in the realm of politics or even pop culture. You can put odds on a lot of different things. Now.

[Sarah Holder]

Yeah, that's disturbing. People betting on something that could destroy people's livelihoods or their lives. But I guess that once you open that door, anything can go on the platform. But Francesca says she's also looking at how the demographics of people using these platforms could shift over time and how that could influence the outcomes of certain bets.

[Francesca Maglione]

Right now, mostly men are users. Maybe we see more women go on there and it become more popular because I do think that it's pretty like the online bro crypto bro environment right now, but maybe, maybe moving forward it'll become more mainstream and maybe more accurate in that way as well.

[Sarah Holder]

What are the implications of the platform having a certain kind of better or a certain kind of user? How might that impact the kinds of predictions it will spit out? And how might that have an impact on real life?

[Annie Massa]

There were these markets on throwing things onto the court at WNBA games and the critique there is you're almost encouraging certain behaviors by posting these certain markets.

[Francesca Maglione]

Yeah, there's some people that are worried that it might influence real life events because some people could say it's biased. And so that's dangerous in the sense that one opinion is getting kind of an advantage over another as more people kind of turn to Kalshi or Polymarket, like I said, to gut check things. And if you're gut checking against kind of a biased opinion, then that might influence real life events or the way that people think about races or things.

[Sarah Holder]

Yeah, yeah. Well, and that's famously one of the impacts of political polls. Right. If you see your candidate leading in the polls, maybe you're less likely to vote or more likely to switch candidates or there are impacts of seeing where the wisdom of the crowd is pointing out.

[Francesca Maglione]

Yeah. And people want to win. And so if you think that an outcome is going to go a certain way because you saw it on Kelshi, then maybe that will make you go that way as well.

[Sarah Holder]

Well, we've got to hope that Taylor was not influenced to get engaged by Polymarket. I'm sure there's more love there.

[Francesca Maglione]

I hope.

[Sarah Holder]

This is the Big Take from Bloomberg News. I'm Sarah Holder. To get more from the Big Take and unlimited access to all of bloomberg.com subscribe [e-mail] podcastoffer if you like this episode, make sure to follow and review the Big Take wherever you listen to podcasts. It helps people find the show. Thanks for listening. We'll be back tomorrow.

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