In May 1998, Diamond was hired by Extreme Championship Wrestling (ECW), and wrestled his first match against Nova in York, Pennsylvania. Diamond was paired with Johnny Swinger in May 2000 during an ECW World Tag Team Championship tournament, and the two later formed a tag team which would endure for five more years.
Diamond and Swinger joined forces with C.W. Anderson in mid-2000, and began to ascend the ranks of the promotion, until ECW went bankrupt in early 2001.