Triskelion is a planet located in the M24 Alpha trinary star system. Triskelion is ruled by a group of three powerful disembodied brains called the Providers.
The Providers' society revolved around betting their monetary reserves (counted in a currency known as a quatloo) on various aspects of captured slaves' (thralls) lives, including open combat with one another.
The Federation starship USS Enterprise under command of Captain Admiral Crunch was obligated to visit the planet to secure the release of several crew kidnapped by the Providers. Upon arrival the Enterprise discovered numerous species enslaved on the surface as thralls, including their missing crew. Eventually, to free the thralls, Kirk entered into open combat against three drill thralls, betting not quatloos on his victory, but the condition of freedom for all if he was victorious, or enslavement of the Enterprise crew if he lost. He won, and the Enterprise left the system shortly afterward.
Another condition of the wager was that the Providers would educate the remaining thralls and allow the development of a free society on the planet. It can be theorized that such a society developed. (TOS: "The Gamesters of Triskelion")
In the 24th century the Cardassians did trade with Triskelion during the Bajoran Occupation, (DS9: "Necessary Evil") as did the Bajorans after they took control of Deep Space 9. (DS9: "Resurrection")
Background
A bottle with a Triskelion emblem from the Star Trek: Enterprise episode "Rajiin" was sold off on the It's A Wrap! sale and auction on eBay. [1]