Chessman was a human male Starfleet officer in the 24th century. Holding the rank of Commander in 2385, Chessman was the commanding officer of a highly classified installation in a star system near the Bretreka Nebula.
The installation was a top secret prison built in to the surface of an asteroid. Hidden under a holographic cloak, the prison was protected by a shield from the radiation of the star the asteroid orbited. The prison was a form of a modern oubliette. The assignment was not one that Chessman chose willingly, but upon his assignment there he strove to carry out his duties to the best of his abilities.
Following the incident at Andoria, Doctor Julian Bashir was arrested by the crew of the USS Warspite. On the Warspite, he was separated from Captain Ezri Dax of the USS Aventine and transported to Chessman's prison asteroid.
Acting on a tip from Sarina Douglas, Commander Christine Vale of the USS Lionheart arrived in system. After she disabled her own ship to keep Chessman from using the prefix codes to force the Lionheart out of the system, Chessman brought her ship under the protective cover of the asteroid in order to repair the ship.
When the Andorian diplomatic ship Kree-thai and the Andorian cruiser ADS Mat-Rus arrived in the system, Chessman was confronted by Ramasanar ch'Nuillan over his detention of Bashir. The situation quickly deteriorated, with Chessman threatening to use physical force against ch'Nuillan and the Andorians, who likewise threatened to use physical force against the Starfleet prison staff in order to free Bashir.
Monitoring the situation from Earth, Chief of Staff Galif jav Velk stepped in before a fight broke out between Starfleet and the Andorians. Using a drone, he holographically projected himself into the docking bay and ordered Chessman to release Bashir to Andorian custody. (ST - The Fall novel: The Poisoned Chalice)