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In 2269, he hired Hikaru Sulu and Pavel Chekov, notorious as "planet killers" in the aftermath of the Talin IV disaster, to join his crew. During the same period, he was engaged in the sale of a number of female Orion slaves, and offered to trade them to another infamous pirate known as Black Ire. During his encounter with Black Ire, Chekov was able to access the Queen Mary's gravity control and incapacitate Krulmadden and the rest of his crew. He was later transferred to the brig of the USS Exeter while at Talin IV. While imprisoned, Krulmadden offered to buy the starship. (TOS novel: Prime Directive)