The Great Escape
High 5 Games just closed the book on one of the most aggressive legal battles a U.S. sweepstakes casino operator has faced. After months of a legal back and forth, the company has agreed to pay more than $1.4 million in a settlement with Connecticut’s Department of Consumer Protection (DCP), and in return, the state has dropped over 1,000 criminal charges and reinstated High 5’s gaming license.
But there’s a twist: the company is still walking away from the state. Permanently.
How It All Started
The trouble started when regulators accused High 5 of running an unlicensed sweepstakes casino through its site, High 5 Casino. The DCP claimed the platform was taking bets from Connecticut residents, including people who had voluntarily banned themselves from gambling through the state’s self-exclusion program.
The fallout was immediate. Connecticut slapped the company with 1,065 criminal charges, froze its supplier license, and even ordered DraftKings and FanDuel to remove High 5’s slot content from their platforms.
It was a regulatory firestorm, and one of the most dramatic enforcement moves the state’s ever taken in online gaming.
The Payout Deal
Here’s how the $1.4 million settlement breaks down:
- $643,000 in restitution is going directly to 794 Connecticut players, refunding what they lost on High 5 Casino while it operated unlicensed in the state.
- Another $800,000 is being funneled into consumer protection efforts. This incudes everything from public education campaigns to complaint resolution, enforcement actions, and litigation.
Importantly, the deal:
- Clears the company of criminal liability — Connecticut formally dropped all 1,065 charges
- Includes no admission of wrongdoing from High 5 Games
- Reinstates the company’s supplier license as of May 22, 2025, allowing it to distribute games again (though High 5 has already pledged to stay out of the state permanently)
No Jail Time, No Return
Had the case gone to trial, High 5 faced real consequences: each of the 1,065 counts carried up to a year in jail and a $2,000 fine. Multiply that, and you’re talking serious time and serious money.
Instead, the company pays, walks away, and keeps its license. But it’s not coming back to the Connecticut market.
What the Regulators Said
Connecticut’s DCP didn’t hold back.
“We are pleased the Connecticut consumers who were lured into placing wagers on an unlicensed platform will be made whole,” said Gaming Division Director Kris Gilman.
Commissioner Bryan T. Cafferelli added: “This case is just one example of the hard work our Gaming Division does to ensure a fair, safe, and legal gaming market.”
High 5’s Side of the Story
High 5’s leadership stood firm on one point: they never believed they were breaking the law.
CEO Tony Singer said the company “operates with integrity, within the law,” and had already begun pulling out of Connecticut before the investigation got serious. In fact, the company claims it started withdrawing from all six regulated iGaming states back in January 2025.
High 5 also confirmed it has now partnered with Xpoint for geo-blocking to ensure it doesn’t accidentally serve users in banned states.
Trouble Beyond the Border
Connecticut isn’t the only place where High 5 has landed in hot water.
- In Maryland, regulators sent the company a cease-and-desist letter in March, accusing it of offering online gaming without legal authorization.
- In Washington State, a jury ordered the company to pay $24.9 million in damages to players after a court ruled that High 5 Casino and High 5 Vegas violated local gambling laws
These back-to-back enforcement actions paint a clear picture: regulators are coming hard for sweepstakes operators that push too far, or get too big.
What This Means for the Industry
This isn’t just about High 5. It’s a warning shot for the entire sweepstakes gaming world.
Connecticut showed that states can and will use criminal charges, not just civil penalties, to crack down on companies they see as stepping over the line. And even when charges get dropped, the reputational damage can stick.
For operators, it’s a wake-up call: you either play by the book, or risk getting burned.
Final Word
High 5 Games dodged the courtroom, but not without cost. With over $1.4 million paid and a market lost, it’s clear the sweepstakes boom is facing a serious reality check.
The industry’s evolving fast. And for those betting on gray zones and loose interpretations? The window may be closing.
Blaise Luis
