Introduction
“Why Waylon Jennings and Merle Haggard Never Stayed Friends”
Despite both being towering figures in country music, Waylon Jennings and Merle Haggard never maintained a close friendship. Their strained relationship did not stem from an immediate dislike, but from a pivotal incident during a difficult time in Waylon’s life.
In his 1996 autobiography, Waylon recounted a devastating tragedy in 1969 when one of his band members, bass player Walter “Chuck” Conway, was killed in a crash on the way to a show in Illinois. Waylon, shaken by the loss and already struggling with drug and alcohol issues, was in a fragile state.
Shortly after, Waylon joined Merle Haggard and Haggard’s manager, Fuzzy Owens, in a poker game. According to Jennings, the game quickly turned into a painful memory: Haggard and Owens “cleaned him out,” taking the $4,000–$5,000 he had on him at the time. Waylon believed they deliberately took advantage of his vulnerable situation. Though he respected Haggard as a singer and songwriter, Jennings admitted he never forgot the feeling of betrayal, recalling how they left him broke and walked away.
While Waylon also acknowledged that Haggard may have been struggling himself as a newer artist in Nashville, the poker game marked a permanent rift. The two legends never collaborated musically, which fans today consider a missed opportunity for what could have been a historic partnership.
In the end, both Jennings and Haggard went on to have remarkable careers that defined country music. Still, their fractured relationship serves as a reminder that even among icons, personal wounds can overshadow professional respect.