In 2265, Jon was the highest Tendaran official and spoke for their planet. He spearheaded a plot to capture Starfleet officers and incarcerate them in their capital city prison as an example of the efficiency and superiority of Tendaran law. Subspace communications signals were sent out as an invitation. The USS Enterprise detected the call, and Captain James T. Kirk initiated first contact. Jon invited him to visit the planet. The moment the landing party beamed down, they were arrested and put in prison.
After Kirk, Spock and Gary Mitchell escaped from the prison, Kirk arrested Jon and Cote, the leader of the prison. Kirk transported them both aboard the Enterprise, where they were first put in the brig, and then were aboard the ship for a few days as Kirk gave them a demonstration of Federation law before they were released. (TOS comic: "Prisoners")