The Truth Will Set You Free
Truth Social is going to enter the prediction market arena after signing a deal with Crypto.com that will include sports contracts.
The Bulletin Board
THE LEDE: Truth Social to launch prediction markets (including sports) through Crypto.com partnership.
ROUNDUP: MA iCasino bill hearing; Netherlands considers legal action against Kalshi; NCAA reconsiders betting policy change; Polymarket’s US debut.
NEWS: A look at Kalshi’s legal fights with states and tribes.
BEYOND the HEADLINE: The central legal arguments.
AROUND the WATERCOOLER: A conspiracy worth considering?
STRAY THOUGHTS: Cabbage Patch Kids, Beanie Babies, Webkinz, and NFTs.
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The Lede: Crypto.com Inks Deal with Truth Social
Trump Media and Technology Group is planning to launch a prediction market (or what appears to be a Frankenstein’s monster version of a sweepstakes-prediction market) on its Truth Social platform. The surprising bit is that it is not with Donald Trump Jr.-aligned Polymarket or Kalshi (Trump Jr. is an advisor to both companies), but with Crypto.com.
But maybe it shouldn’t be that surprising. As Dan Bernstein reminded us yesterday, Crypto.com cofounded a new company with Trump Media in August called Trump Media Group CRO Strategy.
And yes, the press release explicitly mentions sports contracts:
“The event contracts will be offered via CDNA, with the integration providing a federally compliant way to access CDNA event contracts and make predictions on the outcomes of events, including politics, economics, financials, and sports - all seamlessly woven with technology from Truth Social.”
According to the press release:
“Truth Social users will be able to trade prediction contracts related to major events and milestones, such as political elections, interest and inflation rate changes, commodity prices on gold and crude oil, events across all major sports leagues, and more using the new product technology called “Truth Predict.” Prices will update in real-time, allowing users to react instantly to developments in major current events.”
But this is not your average prediction market. As Dustin Gouker put it on X, the Truth Social prediction markets have a strange dual-currency component to them:
Roundup: MA iCasino Hearing; Netherlands v. Kalshi; NCAA Reconsiders Policy Change; Polymarket’s US Debut
November hearing to discuss Massachusetts online casino bills: STTP has learned that the Joint Committee on Economic Development and Emerging Technologies will hold a hearing on November 13, with the state’s online casino bills among the agenda items. The three Massachusetts online casino bills are: HB 332, sponsored by Rep. Daniel Cahill; SB 235, sponsored by Sen. Paul Feeney; and HB 4431, sponsored by Rep. David Muradian.
Netherlands considers taking action against Kalshi [InGame]: Kalshi’s international expansion raised eyebrows, and now it appears to be raising regulatory alarm bells: “Kalshi is walking a regulatory tightrope as it expands globally. The prediction market has no plans to advertise its services outside the US, in what seems to be a move to limit regulatory scrutiny. But the Netherlands’ gambling authority is considering legal action against the platform, and it may not be the only non-US regulator to do so.”
SEC asks NCAA to rescind betting policy change [ESPN]: The SEC has asked the NCAA to rescind the recently approved rule change that would allow athletes and athletic department staff members to bet on professional sports. Per ESPN, “SEC commissioner Greg Sankey sent a letter to NCAA president Charlie Baker on Oct. 25, stating that during an Oct. 13 conference meeting, ‘The message of our Presidents and Chancellors was clear and united: this policy change represents a major step in the wrong direction.’” The NCAA has decided to delay the effective date to November 30, giving each Division I school the opportunity to rescind its decision.
Polymarket’s US launch draws closer [Bloomberg]: From Bloomberg: “Prediction market Polymarket is preparing to return to the US in the coming weeks with a focus on sports betting, according to people familiar with the matter. Initial trading is likely by the end of November but won’t be broadly available to everyone, said some of the people who asked not to be identified, discussing the confidential plans.”
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News: A Rundown of Kalshi’s Court Cases
Author’s Note: There was a significant ruling in Massachusetts yesterday, covered below.
I’ve been joking that the last 12 months have seen the TikTokification of gambling news, but the legal department at Kalshi is just as busy.
Kalshi has sued five states after receiving cease-and-desist letters:
Nevada
New Jersey
Maryland
Ohio
New York
It has been sued by the state of Massachusetts and tribes in California and Wisconsin.
And that’s just Kalshi. Crypto.com and Robinhood are also suing and being sued. Nor does it include the class action and Statute of Anne lawsuits that have been filed.
Here’s where each of those cases stands (if you’d like a deeper dive, I recommend my recent podcast with attorney Andrew Kim), and as others have noted, Kalshi’s early victories have begun to tail off:
Kalshi vs. Nevada (Leans Kalshi Tossup)
Kalshi filed its lawsuit on March 28, 2025, following a cease-and-desist letter. A federal judge granted a preliminary injunction on April 9, 2025, blocking state enforcement. Nevada received a boost from potential tribal involvement, as well as a parallel case involving Crypto.com, in which the same judge ruled against the prediction market. The case remains ongoing, with a hearing on Nevada’s motion to dismiss the preliminary injunction scheduled for November 14, 2025.
Kalshi vs. New Jersey (Leans Kalshi)
Kalshi filed its lawsuit on March 28, 2025, and secured a preliminary injunction in federal court on April 28, 2025, blocking state enforcement. The state appealed the decision to the US Court of Appeals for the Third Circuit, with support from a coalition of state attorneys general backing New Jersey.
Kalshi vs. Maryland (Leans Maryland)
Kalshi also challenged Maryland’s cease-and-desist with a lawsuit on April 22, 2025, but a federal judge denied its request for a preliminary injunction on August 1, 2025, allowing state enforcement to proceed. Kalshi appealed to the US Court of Appeals for the Fourth Circuit. On August 13, 2025, the parties agreed to pause enforcement pending the Fourth Circuit’s ruling, and Kalshi withdrew its motion for an injunction pending appeal. Kalshi’s opening brief was due by September 15, 2025, and Maryland’s response brief is due by October 15, 2025.
Massachusetts vs. Kalshi (Leans Massachusetts)
Massachusetts Attorney General Andrea Joy Campbell filed suit on September 12, 2025, in state court, accusing Kalshi of unlicensed sports wagering and seeking to halt operations in the state. This was the first time a state preemptively sued Kalshi, which is where things suddenly got dicey.
An emergency motion for a preliminary injunction was filed by Kalshi, with a hearing initially set for September 22, 2025, and Kalshi’s response due September 19, 2025. And then on September 16, 2025, Kalshi filed a notice of removal, transferring the case to federal court. Robinhood filed a separate federal lawsuit against Massachusetts on September 15, 2025, to block enforcement. On Tuesday, the court issued its decision, which is the most significant legal blow to Kalshi thus far, as the case has been remanded to the state court.
Kalshi vs. Ohio (No line available)
Kalshi filed suit on October 7, 2025, against the Ohio Casino Control Commission following a cease-and-desist order, seeking an injunction and arguing that federal preemption applies. No rulings have been issued yet, and the case is in its early stages.
Kalshi vs. New York (No line available)
Most recently, Kalshi filed a federal lawsuit in the Southern District of New York on October 27, 2025, against the state gaming commission, seeking to block a recent cease-and-desist order, claiming that CFTC jurisdiction overrides state gambling rules. This is the latest action, with no court decisions yet, but Kalshi has filed for an emergency temporary restraining order and an immediate hearing.
California Tribes vs. Kalshi (Leans tribes)
Three tribes filed the lawsuit on July 22, 2025, alleging violations under the Indian Gaming Regulatory Act. A hearing on the tribes’ motion for a preliminary injunction was held on October 23, 2025, during which the judge expressed skepticism toward Kalshi’s arguments but issued no ruling. The decision on the preliminary injunction remains pending, with no specific timeline reported.
Ho-Chunk Nation (WI) vs. Kalshi (No line available)
The Ho-Chunk Nation filed the lawsuit on August 20, 2025, alleging violations under the Indian Gaming Regulatory Act. The tribe also alleges Kalshi forms an “enterprise” of illegal gambling under RICO, breaching tribal-state compacts beyond just IGRA. No rulings have been issued, and the case is ongoing.
Beyond the Headline: What are We Fighting Over
Kalshi’s Core Arguments: The Commodity Exchange Act (CEA) provides the CFTC with exclusive jurisdiction over event contracts, preempting state gaming laws. Kalshi asserts that states cannot regulate the federally approved platform because such regulation would conflict with federal law and urges states to challenge the CFTC directly if dissatisfied.
States’ Core Arguments: States contend that Kalshi’s contracts constitute gambling and that the CEA does not preempt state gaming laws, as gambling regulation is a traditional state domain with a presumption against federal preemption. Nor is there a “clear and manifest” congressional intent to override state laws.
Tribes’ Core Arguments: Kalshi’s contracts violate IGRA by offering Class III gaming (sports wagering) without tribal compacts, occurring on tribal lands.
A Secondary Argument: What is “gaming” in the Commodity Exchange Act (CEA)? Section 5c(c)(5)(C) of the CEA prohibits designated contract markets from listing or trading event contracts involving activities such as terrorism, assassination, war, gaming, or other activities contrary to the public interest. The term “gaming” is not explicitly defined in the CEA, but the CFTC has proposed providing more clarity, but has never officially updated the definition. States and tribes argue that prediction markets on sports or elections fall under this as unlicensed gaming, while Kalshi contends that CFTC approval overrides this classification. Kalshi’s previous arguments on this front contradict its current arguments. In 2024, it argued in its D.C. Circuit election markets case that sports contracts involve “gaming.”
Beyond the gaming clause’s lack of definition, the Special Rule also allows the CFTC to prohibit contracts if they violate state laws or are contrary to public interest. States argue this preserves their authority, while Kalshi flips it to claim it “supports” federal jurisdiction over sports contracts, since the CFTC hasn’t prohibited them.
A Tertiary Argument: How much does it cost to geofence? Geolocation is a central argument in Kalshi’s lawsuits, focusing on whether event contracts constitute betting at the user’s physical location (potentially violating state or tribal laws) or the platform’s server location. The tribal lawsuits in California and Wisconsin claim bets occur where the user is, implicating IGRA violations, while Kalshi counters by adopting Florida’s server-based interpretation (the hub-and-spoke model used by the Seminole Tribe) and argues implementing user-based geofencing would cost tens of millions, take months, cause irreparable harm, and conflict with CFTC impartial-access rules requiring nationwide uniformity.
Maryland and Nevada have demanded evidence through discovery of Kalshi’s “tens of millions” geofencing claim, arguing it’s feasible (like sportsbooks do) without conflicting with CFTC rules. Crypto.com’s recent decision to exit Nevada also undermines this claim.
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Around the Watercooler
Social media conversations, rumors, and gossip.
Given the Crypto.com-Truth Social news, maybe there is something to what I always dismissed as a conspiracy theory.
Stray Thoughts
I’m not much of a ‘hot take’ guy, and I try not to overreact to things. I’m also getting old[er], and have seen my fair share of flash-in-the-pan crazes, from Cabbage Patch Kids to Beanie Babies to Webkinz to NFTs.
The point is, a lot of stuff comes and goes, and the same goes for most ‘game-changing’ ideas. Whether it’s the DeLorean, the Segway, 3D TVs, or any number of recent tech devices that have failed to capture the general public’s attention.
The point being, true change takes time. It’s introduced, its utility is evident, and over time, more and more people start using it until there is a tipping point: Vinyl to Tape to CD to Digital to Streaming.
It builds on what works, adapts to how we actually live, and sticks around because it solves problems without demanding we rewrite our habits overnight. They become so woven into our daily lives that we forget there was ever a before time.
This notion that change requires upheaval just doesn’t ring true. Real progress sneaks up on you; it’s not forced down your throat. It’s evolutionary, not revolutionary.
The crazes are like my second-favorite Bad Company song; they burn bright for a hot minute and quickly fizzle out.