In 2001 within the framework of the lawsuit “United States of America v. Jay Cohen”, the court prosecuted American citizen who started sports betting services in Antigua. Cohen had consulted with lawyers and accountants to make sure that his actions are legal. Nevertheless, he was convicted in relation to breaking one technical detail of bookmaking law.
This case is interesting because of differences in Judge James Oliver's opinion and actively promoted political and public views regarding online gambling as a whole. James Oliver highlighted the inadequacy of the law that regulated internet, and stated that online gambling can't be prohibited.
Thompson v. Handa-Lopez lawsuit is related to the situation when online gambling operator from California refused to pay winnings to the plaintiff. The gambling website was working legally in California State because players got play credits called "Funbucks" and later those credits could be exchanged to prizes. This case is interesting since it's a legal precedent that can be quoted in cases when a company offers services on gambling website that are legitimate in one place, and customers using those services are located in different jurisdiction. This also shows that not every online gambling site should be trusted.