Tradewinds operator avoids prison after pleading guilty to illegal offshore sportsbook

Costa Rica-based businessman Michael Lawrence “Scott” Brannon will not serve prison time after pleading guilty to helping run Tradewinds, an offshore sportsbook that took in at least $25m. For high-risk operators, the useful part here is not the personality drama; it is the federal treatment of offshore gambling revenue, forfeiture, and the long tail of gambling-related exposure.

1. In the U.S. District Court for the Eastern District of Texas, Brannon pleaded guilty in February to operating an illegal gambling business. The court sentenced him to 12 months of probation, including six months of home confinement.
2. The remaining probation period may be served in Costa Rica, where Brannon resides. His probation began on April 6, 2026, and bars him from owning, managing, operating, consulting for, or otherwise participating in any gambling business.
3. Brannon admitted to conducting, directing, and financing Tradewinds between August 2013 and April 23, 2021, and said he worked with at least five other people. He also acknowledged receiving at least $25m from the operation and agreed to forfeit the full amount.
4. He must pay $7m shortly after sentencing, with the remaining $18m to be paid in three instalments after he completes home confinement. The forfeiture also covers Tradewinds’ website, trdwd.cc.
5. Brannon is the second person to face federal prosecution over Tradewinds, which was operating from Costa Rica by at least the late 1990s. Clarence “Gary” Austin pleaded guilty in 2023 after federal authorities raided his Florida residence in 2021 and received five years’ probation, including six months of home detention.

For PSPs and acquiring teams, the signal is familiar: offshore sportsbook revenue can turn into a forfeiture case years later, and the asset list can be broader than cash alone. Austin’s surrendered assets included 61 one-kilogram gold bars, cryptocurrency, funds held in financial accounts and investment products, luxury vehicles, and three properties in Florida.