This essay examines the changes in regulatory control of gambling, especially illegal lotteries, in the Philippines. There, as in other modern states, the government has regarded gambling as problematic immoral behavior since the colonial era and has operated legal forms of gambling while prohibiting other forms. However, once democratic politics was introduced during the American colonial era, illegal lotteries expanded as a source of campaign funds, protected by corrupt politicians and polices. Since then, illegal lotteries have gained nationwide popularity, and illegal gambling syndicates have grown to be important political financers. Although the central government has resisted corruption by creating and promoting state-run gambling, all attempts to eliminate illegal activities have failed; even presidents have been corrupted and have benefited from the illegal market. To overcome a hotbed of corruption and reduce illegal activities, the current Philippine government led by President Duterte is strongly seeking to secure a monopoly over all forms of gambling in the country. Duterte’s policy of legalizing illegal lotteries is intended to monopolize a huge source of political funds generated by the gambling market.