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In 1988, Calaway joined the Continental Wrestling Association (which became part of the United States Wrestling Association (USWA) after Jerry Jarrett bought WCCW and merged the two organizations into one), wrestling under several gimmicks. On February 2, 1989, managed by Dutch Mantel, he was reintroduced as The Master of Pain, a character fresh out of the United States Penitentiary, Atlanta after serving five years (much in solitary confinement) for killing two men in a fight. After his second match the next week, he stayed in the ring by challenging USWA Unified World Heavyweight Champion Jerry Lawler to an impromptu match. The Master of Pain easily dominated Lawler until Mantel entered the ring and called him off. Lawler agreed to a title match and on April 1, The Master of Pain won his first professional wrestling championship. He held it for just over three weeks before Lawler became the first man to pin him, winning it back. While performing as The Punisher, Calaway won the WCWA Texas Heavyweight Championship on October 5, 1989, when Eric Embry forfeited the title.