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Heir apparent to a countship on the backwater world of Rybinsk in the Duchy of Oriente, Andrei Chekhov rejected the sheltered noble lifestyle to instead pursue a dream of rugged adventure and daring-do as a hired gun. Spending his first few years unsuccessfully attempting to build his reputation as an independent contractor in the rimward Periphery, in 3020 Chekhov fell in with a relatively influential band of pirates known as Porter's Pillagers. However, despite the boon this provided to his reputation, Andrei quickly became disenfranchised by the group's lack of discipline and camaraderie, and in February 3021 when the group was targeted by a group of Inner Sphere mercenaries known as Crowe's Bloody Buccaneers, he hardly hesitated to sell the Pillagers out, even aiding the Buccaneers in the engineering of their destruction.

Impressed by his skills as a MechWarrior, the Buccaneers' leader, Bayard Crowe, offered Andrei a place in his personal lance. Andrei, himself suitably impressed by the Bloody Buccaneers, accepted. Andrei would go on to have a storied career with the Buccaneers, stretching until 3065, being the last to retire out of Bayard and his lancemates, despite being second-eldest.

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