Read in Browser [[link removed]]

Sunday Edition

November 30, 2025

POWERED BY

Perhaps you’ve seen tweets or Instagram posts from Kalshi and Polymarket that make you do a double take. From the f-bombs to the fake news, it may be hard to believe these are coming from the official accounts of companies with valuations in the ballpark of $10 billion. But supporters say it’s “authenticity” in today’s internet culture.

— Dan Roberts [[link removed]]

Polymarket and Kalshi Are Shitposting Their Way to Legitimacy [[link removed]]

@kalshisports/@polymarketsports/Front Office Sports

Polymarket and Kalshi, the two household names in the exploding prediction-markets race, are on quite a ride.

Polymarket was valued at $8 billion [[link removed]] in October after a $2 billion investment from New York Stock Exchange parent company ICE, and it is reportedly seeking more funding [[link removed]] at a valuation of up to $15 billion. Kalshi this month reportedly raised a fresh $1 billion that brought its valuation to $11 billion [[link removed]]. Both have a slew of key sports league partnerships, including with the NHL (both), UFC (Polymarket), Pro Padel (Kalshi), and Pro Pickleball (both).

Polymarket and Kalshi, through their rise, have pushed bigger players—including DraftKings, FanDuel, Robinhood, CME Group, Susquehanna, Fanatics, and even Trump Media—to snap to attention and jump into prediction markets.

Polymarket and Kalshi have posted AI-generated images of Joe Biden in a football helmet and diaper ( Kalshi [[link removed]]), an image of WNBA star Angel Reese and NBA player Wendell Carter Jr., who are dating, with the headline: “FUCKIN” ( Polymarket [[link removed]]), an image of 49ers running back Christian McCaffrey with the caption “LOVES RECEIVING BALLS” ( Kalshi [[link removed]]) and an image of Toronto Raptors player Gradey Dick with the headline “DICK IS GROWING” ( Polymarket [[link removed]]).

Both companies pay affiliate accounts on X/Twitter for engagement farming, a strategy that has gotten both in trouble [[link removed]]—in two of the more high-profile incidents, for racism toward Indians [[link removed]]. And after Polymarket CEO Shayne Coplan had his apartment raided by the FBI, two Kalshi employees DM’d former NFL player Antonio Brown [[link removed]] instructing him to retweet a photo of Coplan and say, “This ni**a seem guilty.” Brown complied.

‘It’s the Age of Authenticity’

So is their shitposting on social media at odds with their serious business momentum? I asked Nick Tomaino, an early investor in Polymarket through his VC fund 1confirmation.

“No,” he says. “It’s the age of authenticity. It’s not financial firms playing the game the way they think it should be played, saying the same boring, politically correct shit. The reason the Polymarket brand is so strong is it’s authentic. Also, it’s done tastefully. No one is offended, right? It’s just funny. Young people like it.”

He’s probably right. While some may clutch their pearls at the language and flippancy of the posts, it’s internet culture in 2025. The Overton window has shifted tectonically. More specifically in the case of Polymarket (which takes deposits only in crypto), it’s “degen” culture, the meme lexicon of the “terminally online” who trade crypto and stocks with the swipe of a finger and coalesced around the retail investor revolution during the pandemic.

The culture on Elon Musk’s X/Twitter is closer to a gambling Discord chat than a Wall Street happy hour.

You might wonder whether the suits at, say, the NHL offices are cool with the posts, but all smooth so far. The NHL declined to comment on the social media posts of their new partners, but this week, in a CNBC hit, league commissioner Gary Bettman talked up prediction markets and said a benefit of being in official partnerships with both is that the league could ask the companies to remove [[link removed]] event contracts it doesn’t like. (It hasn’t yet had to.)

You might also wonder whether the posts make the vaunted parent company of the NYSE uneasy about its $2 billion bet. “I’m sure some of the boomers at these big organizations don’t get it,” Tomaino says. “I can tell you [ICE CEO] Jeffrey Sprecher gets that Shayne gets the younger generation. He gets that Polymarket has a finger on the pulse. I’m sure there will be people at these organizations that don’t get it and maybe get pissed off by some of the stuff, but Polymarket has done a really good job building an edgy brand without any major issues.”

Tomaino also frames prediction markets as replacements for mainstream news outlets. “The information it provides is more truthful than a media narrative,” he says.

Indeed, I asked a friend who is an avid user of Polymarket for his take on the social media posts. He wrote me, “There’s a certain ‘The media thinks we’re not real companies because we’re funny, LOL.’”

Kalshi declined to comment for this story. Polymarket and ICE didn’t respond to a request for comment.

[[link removed]]Kalshi newsletter Shades of DraftKings vs. FanDuel

The entire premise of prediction markets relies on the “wisdom of crowds” theory, so it’s fitting that they would have a social media tone that screams directly at their target user base (young, male, very online), even if many outside of their intended base find it cringe-inducing.

On prediction markets, each bet is an “event contract” where you, the bettor, are trading futures. If that argument sounds like a stretch, tell the Commodity Futures Trading Commission, which under President Donald Trump has given its blessing to this framing.

In 2024, during the Biden Administration, Kalshi took the CFTC to court over its event contracts on political elections, and won; the CFTC appealed the ruling, but once Trump regained office, it dropped the appeal. Polymarket, which was completely banned from operating in the U.S. under a 2022 settlement with the Biden Administration, has since been given the green light to operate in the U.S., but hasn’t relaunched here yet. (Donald Trump Jr. is a strategic advisor to both direct competitors.) Last week, Polymarket dropped a new ad campaign [[link removed]] with the tagline, “The world’s largest prediction market—now CFTC approved.” Separately, Kalshi is still mired in a bitter court battle with the state of Nevada [[link removed]], where casinos are king.

All of this head-to-head competition, as well as federal and state-by-state legal battles, looks a lot like DraftKings vs. FanDuel in 2015. I covered their rise closely for Fortune and then Yahoo Finance as they fought state attorneys general who argued their daily fantasy sports contests were a form of illegal gambling; in 2018, it all became moot when the U.S. Supreme Court struck down PASPA, the federal law that banned sports betting in most states. That allowed states to legalize sports betting on an individual basis (nearly 40 have), and DraftKings and FanDuel were able to break the shackles of their “DFS” limitations and go whole hog with sportsbooks.

Now it’s history repeating. Kalshi and Polymarket have their key differences but look like basically the same company. DraftKings and FanDuel stunned onlookers when they announced in 2016 they would merge [[link removed]]; eight months later, they called it off [[link removed]] after regulators signaled they would not bless the union.

DraftKings, now publicly traded, and FanDuel, owned by Flutter Entertainment, are currently the two top dogs in legal online betting in the U.S. Polymarket and Kalshi are the duopoly in prediction markets, but they run the risk of getting copied and killed by established giants.

Robinhood and market-maker Susquehanna announced [[link removed]] Wednesday they’ve acquired crypto exchange LedgerX (formerly owned by disgraced exchange FTX [[link removed]]) to launch a dedicated exchange for prediction markets. It was bad news for Kalshi, which had a partnership with Robinhood for the football season that has been hugely beneficial to Kalshi (some 90% of its volume is now in sports predictions). Crypto.com, the company with its name on the Lakers arena, launched prediction markets, and Fanatics says it will join them [[link removed]]. DraftKings spent up to $250 million [[link removed]] to acquire prediction market Railbird.

It’s a very crowded room. And the battle that started in politics is now playing out in sports.

“What has happened in sports in particular has been surprising to me,” Tomaino says. “It’s crazy how quickly the DraftKings and FanDuels and Fanatics are getting into this game, because they get it. If you are betting on sports and it’s a binary bet where you win or lose, that’s not as good a product. That’s not as fun.”

SPONSORED BY APPLE SPORTS APP

Football Scores, Fast and Simple

[[link removed]]

The Apple Sports app [[link removed]] delivers a quick and simple way to stay locked in on every game. Fans get real-time scores, live stats, and play-by-play in an incredibly clean, fast, and intuitive Apple-designed experience.

Follow your favorite teams, leagues, and conferences all in one place. Personalize your dashboard, track game flow through detailed box scores, and get Live Activities delivered straight to your iPhone Lock Screen or Apple Watch.

If you want the sport, not the clutter, the Apple Sports app gives you exactly what matters.

👉 Download Apple Sports for free on the App Store [[link removed]].

Opinion Tanking Is Killing Pro Sports More Than Gambling Ever Could

Darren Yamashita-Imagn Images

In other legal betting news: Even amid a slew of recent gambling scandals across the NBA, MLB, and college basketball, FOS contributor Bradford William Davis [[link removed]] writes that there’s a far more pernicious practice [[link removed]] hurting the integrity of the competition.

Advertise [[link removed]] Awards [[link removed]] Learning [[link removed]] Events [[link removed]] Video [[link removed]] Show [[link removed]] Written by Daniel Roberts [[link removed]] Edited by Dennis Young [[link removed]], Meredith Turits [[link removed]], Catherine Chen [[link removed]]

If this email was forwarded to you, you can subscribe here [[link removed]].

Update your preferences [link removed] / Unsubscribe [link removed]

Copyright © 2025 Front Office Sports. All rights reserved.

460 Park Avenue South, 7th Floor, New York NY, 10016