JYD began a main event run in May 1990. On May 20 he defeated Mean Mark Callous in 39 seconds. He quickly became embroiled in a feud with Ric Flair for the World Heavyweight Championship. After gaining disqualification and non-title victories in house show matches, JYD would give Flair a televised defeat by DQ on June 13 at Clash of the Champions XI. JYD would then be part of the short-lived Dudes with Attitudes faction along with Sting, Paul Orndorff, and El Gigante. In the fall he would feud with Television Champion Arn Anderson, defeating him in non-title matches in less than 10 seconds on three house shows in September. He would finish the year defeating Moondog Rex, The Iron Sheik, and Bill Irwin on the house show circuit.