Ritter would make his debut for the National Wrestling Alliance on December 7, 1988 at the Clash of the Champions IV. He would appear during an altercation between The Russian Assassins and Ivan Koloff, saving the latter. His first match came shortly after in a television taping in Atlanta against Trent Knight. JYD finished the year winning a $50,000 bunkhouse battle royal on December 26, which was held as a dark match after Starrcade '88 went off the air. He spent the first few months of 1989 teaming with Ivan Koloff and then Michael Hayes against The Russian Assassins. On April 2, 1989 JYD defeated Butch Reed at Clash of the Champions VI in New Orleans. Before the match he was accompanied to the ring by a jazz band.