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August 31, 2025 15 mins

Gamblers on prediction sites like Polymarket and Kalshi are already trying to cash in on Taylor Swift and Travis Kelce’s engagement — betting on everything from their wedding timeline to her next single.
On today’s Big Take podcast, host Sarah Holder sits down with Bloomberg personal finance reporter Francesca Maglione and wealth reporter Annie Massa to dig into what a high-profile engagement can teach us about the rapidly growing predictions industry, the challenges with regulating it and who’s investing in its future.

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Speaker 1 (00:00):
Bloomberg Audio Studios, Podcasts, radio News. Would you consider yourself
a swifty? I think it's a scale, like oh, so
many group chats. This week, I found myself talking with
my coworkers about Taylor Swift.

Speaker 2 (00:19):
I like music, but I'm not like keeping up with
every single thing she does with her life.

Speaker 1 (00:24):
That's Bloomberg's Personal Finance reporter Francesca Maglione. I am a
big fan, and that's Annie Massa, a Bloomberg Wealth reporter.

Speaker 3 (00:32):
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 last week. Yes.

Speaker 1 (00:48):
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 predictions and financial bets on where their relationship will
go next.

Speaker 2 (01:07):
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 twenty twenty five, and I
had said that they were going to break up, so
I think I was expecting that at all.

Speaker 1 (01:19):
Did you lose money on that bet?

Speaker 2 (01:20):
No? No, no money was involved, thankfully.

Speaker 1 (01:24):
The rise of legal online betting in the US over
the last few years has ushered in all kinds of
vets like bets on current events and pop culture made
on prediction markets like Polymarket and call She.

Speaker 2 (01:38):
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.

Speaker 1 (01:46):
Within hours of Tailor and Travis's announcement, gamblers on call
She had placed about eighty thousand dollars worth of bets
on the couple's wedding timeline, and by Thursday that number
had doubled to around one hundred and sixty thousand dollars.

Speaker 3 (02:00):
Yes.

Speaker 1 (02:01):
By Thursday afternoon, the odds of Taylor and Travis getting
married by the end of the year hovered at around
seven percent.

Speaker 3 (02:08):
I was not placing any bets personally, but I was
kind of bearish. So here we are and very happy
for them, obviously.

Speaker 1 (02:14):
Yeah, bullish now on.

Speaker 3 (02:15):
Travis and Taylor one hundred percent.

Speaker 1 (02:22):
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

(02:44):
markets like polymarket and call She have recently surged in
popularity in the US. If I've never used polymarket before
or call she. Is this like sports betting or is
it different? How does it actually work?

Speaker 3 (02:59):
The easiest explanation would be, in the context of a
presidential election, who will win Kamala Harris or Donald Trump?

Speaker 1 (03:06):
That's Bloomberg Wealth reporter Annie Massa.

Speaker 3 (03:09):
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 no?

Speaker 1 (03:25):
And gods of that went up significantly?

Speaker 3 (03:28):
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 for depending on
the type of market it is.

Speaker 1 (03:39):
Polymarket was founded in twenty twenty and it's gotten major
funding support from Peter Teel and Ethereum founder Vitolic Buterine.
This year alone, it's nearly two hundred and thirty thousand
monthly users have placed nearly sixteen billion dollars of bets
on real world events. Here's Francesca Magleone, Bloomberg's Personal Finance reporter.

Speaker 2 (04:00):
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 she is she going to have
a baby this year? Like when are they going to
get engaged? Is the wedding going to happen this year?
Like anything you could think of people are betting on.
There's a market for that for.

Speaker 1 (04:19):
Sure, and what happens when you win and what happens
when you lose, like how much money is on the
line here.

Speaker 3 (04:25):
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.

Speaker 1 (04:45):
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 tonight, 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 in a 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

(05:08):
either get your payout or you lose.

Speaker 2 (05:11):
There's been some studies that have said that Americans are
taking money out of their brokerage accounts to fund some
of these wages, and in extreme cases there's losses from
gambling that can contribute to autolone delinquencies and bankruptcies.

Speaker 1 (05:25):
Is this part of a broader trend of online betting
markets gaining popularity like DraftKings or other websites.

Speaker 2 (05:31):
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.

Speaker 1 (05:46):
What is a company like this worth.

Speaker 3 (05:48):
So actually, both Calshie and Polymarket have been fundraising, and
Calsh's valued at two billion dollars 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

(06:10):
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 Calshi.
So again like a mix of both the more Silicon
Valley side of things and the Wall Street side of things.
And Founder's Fund is a big backer of poly.

Speaker 1 (06:30):
Market and some other notable backers like Donald Trump Junior.

Speaker 3 (06:35):
Donald Trump Junior 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
Calshy and just became an advisor to Polymarket, and he

(07:00):
is a partner at this firm called seventeen eighty nine Capital,
which invested in Polymarket.

Speaker 1 (07:06):
Why is he so interested in this company?

Speaker 3 (07:08):
He said when he took the role at Calshi that
prediction markets allowed him and his family, when they were
watching the returns for the twenty twenty four 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

(07:31):
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, Calshi 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

(07:52):
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.

Speaker 1 (08:05):
Time, controversial, not only because of that murky regulatory landscape,
but because of the real world implications of betting on
real world events.

Speaker 3 (08:15):
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

(08:37):
or sick markets on things, And is that really a
good idea to start putting that out for people to
win money on.

Speaker 1 (08:45):
Yeah, it's a really thorny ethical question. Yeah, 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.

(09:07):
A few years after prediction markets hit the scene, the
industry faced a major roadblock. People were flocking to sites
like polymarket and call she, 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

(09:30):
derivatives market, which, unlike traditional gambling, is not regulated by
the States.

Speaker 3 (09:36):
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

(09:58):
Calshi and Polymarke have had their own skirmishes in the
regulatory arena.

Speaker 1 (10:03):
The CFTC first targeted call She back in twenty twenty three.
The regulator claimed that the political betting the platform facilitated
was illegal and ordered them to stop operating, but Call
she sued and after a federal court battle, the CFTC
dropped its appeal in May of this year.

Speaker 3 (10:20):
But the tension for Polymarket had to do with two
separate inquiries. There was 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

(10:44):
customers to bet on outcomes and trade contracts that are
basically something that we should be regulating. You need to
register with US.

Speaker 1 (10:51):
In twenty twenty two, the US banned Polymarket outright. That
meant US based users weren't allowed to place bets on
the site.

Speaker 3 (10:59):
Polymarket was almost an exile in some ways just for
the US.

Speaker 1 (11:03):
That didn't stop the site from featuring bets about the US.
In twenty twenty four, 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
was kind of like an informal poll that actually ended

(11:24):
up being more accurate.

Speaker 2 (11:25):
Yeah, I have a friend that anytime something going on,
she just goes on Calshien is like, yeah, no, we
don't have to worry about this or low or whatever
the case might be.

Speaker 1 (11:32):
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 clearing house called QCX,
which gave them stronger legal standing to operate in the US.
You both mentioned how influential Polymarket and Calls's predictions have

(11:57):
grown as a cultural force a political course. Where do
you see that influence going next.

Speaker 2 (12:03):
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, Like, will.

Speaker 3 (12:16):
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 un towered.
So it can go all over the place. It's not

(12:36):
just in the realm of politics or even pop culture.
You can put odds on a lot of different things.

Speaker 1 (12:41):
Now, 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 outcome of certain bets.

Speaker 2 (13:01):
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 moving forward it
will become more mainstream and maybe more accurate in that
way as well.

Speaker 1 (13:17):
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.

Speaker 3 (13:30):
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.

Speaker 2 (13:45):
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 Calci or polymarket, like I said,
to gut check things, and if you're a gut checking
against kind of a biased opinion, then that might influence
real life events or the way that people think about

(14:06):
races or things like that.

Speaker 1 (14:08):
Yeah, yeah, well, and that's famously one of the impacts
of political polls.

Speaker 3 (14:14):
Right, if you see your.

Speaker 1 (14:15):
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 and.

Speaker 2 (14:24):
People want to win, and so if you think that
a outcome is going to go a certain way because
you saw it on Calshi, then maybe that will make
you go that way as well.

Speaker 3 (14:33):
Well.

Speaker 1 (14:33):
We've got to hope that Taylor was not influenced to
get engaged by poly market. I'm sure there's more love.

Speaker 3 (14:40):
There, hope.

Speaker 1 (14:57):
This is the Big Take from Bloomberg News Sarah Holder.
To get more from The Big Take and unlimited access
to all of Bloomberg dot com, subscribe today at Bloomberg
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