In 2265, during a visit to the planet Orthoo by the USS Enterprise, Captain James T. Kirk volunteered to protect the Great Eye of Ara for King Yo. Kirk assigned Sergeant Loi as the outer security guard detail and Red Garvin to the inner guard detail. The ruby disappeared one night and could not be located. In reparation, Kirk paid King Yo 20 million credits.
In 2266, Garvin found an opportunity to sneak aboard the Enterprise with two accomplices. He intended to retrieve the ruby he'd stolen and left hidden in a ventilation grid in his former quarters. But Kirk and Leonard McCoy confronted them. During the ensuing fight, McCoy threw the ruby against the head of one of the criminals, who was knocked unconscious by the blow. The criminals were apprehended and the ruby recovered. (TOS comic: "Furlough to Fury")