David H. Stewart Sentenced in $4.2M Internet Gambling Scam

Digital smoke and mirrors turned real-life prison bars for David H. Stewart, 65, of Holly Hill, Florida. On Thursday, U.S. District Judge Paul G. Byron slapped Stewart with a 41-month federal prison sentence for his central role in a $4.2 million wire and bank fraud conspiracy tied to illegal offshore internet gambling operations. The judgment lands hard after years of deception that exploited U.S. financial systems in broad daylight.

Stewart pleaded guilty on June 28, 2016, to conspiracy to commit wire fraud and bank fraud. Court records lay bare a scheme built on lies: Stewart and co-conspirator Jason Neiman created a fake online business, DiamondPayTV, claiming it sold digital movie and television subscriptions. In reality, it was a front funneling illicit gambling proceeds through shell companies and directly into overseas casino accounts.

The fraud was industrial in scale. Over just 12 months, the operation processed more than 59,000 credit card transactions, disguising illegal bets as routine entertainment payments. Financial institutions and a major credit card processor were duped into handling the cash flow, believing they were supporting a legitimate tech venture. Stewart personally opened business bank accounts under the names of ghost companies and fed the stolen stream of funds across borders.

He didn’t just hide the truth—he weaponized it. Stewart repeatedly lied to bank officials about the nature of the businesses to secure account access, fabricating business models and falsifying documentation. The ruse worked long enough to siphon $4.2 million in illegal gambling revenue, leaving banks exposed and regulators scrambling.

The court didn’t let him walk with scraps. Judge Byron entered a money judgment of $323,636—the full amount traced as proceeds of Stewart’s criminal conduct—and ordered the forfeiture of his interest in a parcel of real property, likely bought with dirty cash. The sentence sends a message: digital fraud may leave no blood, but it carries real-time consequences.

Cracking the case took a regional army. The Saint Cloud IRS-Secret Service Financial Crimes Task Force led the charge, pooling resources from the Internal Revenue Service-Criminal Investigation, U.S. Secret Service, and law enforcement agencies across Central Florida—including the Osceola County Sheriff’s Office, Palm Bay and Kissimmee Police, and others. Prosecution was handled by Assistant U.S. Attorney Karen L. Gable, who tied the digital trail to a man who thought he could game the system and vanish into the Florida heat.