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Chessman was a human male and Starfleet officer. 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 that Chessman was the commanding officer of 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.

For the next 17 days Bashir was held in solitary confinement on the prison asteroid. Chessman and his crew followed orders and did not talk to Bashir during this time.

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.

Chessman was quite hostile towards Vale during this time, alternatively threatening to have her arrested and shipped to the nearest Starbase in chains or putting her in the cell next to Bashir's.

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)

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