The saddest story in country music? Quite possibly, if you think too much about the music that could've been... When you think back on great pairings in country music history, Waylon and Willie always come to mind first for me, and obviously the supergroup The Highwaymen comprised of Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson is iconic too. But there's one classic country name you'll never see next to
Waylon Jennings , and that would be the late, great
Merle Haggard . Unfortunately, early in their career, an incident occurred that stuck with Waylon forever, and resulted in zero music or collaborations form the two of them, even though their friends were friends with each one and vice versa. Here's what went down... On February 9th, 1969, tragedy struck in Waylon Jennings' camp, as one of his band members was killed in an accident en route to a show in Illinois. Another was badly injured, and it obviously shook Waylon to his core and left him reeling. Waylon wasn't with them at the time, but he was in the thick of his drug addiction and it just made everything that much worse. Down on his luck and in a pretty dark place, not long after that incident, Waylon sat down for a poker game with Merle and his manager, Fuzzy Owens. He explained it all in his 1996 book
Waylon: An Autobiography , and after some very bad luck that night, and they wound up wiping his pockets clean of every last cent he had on him, which was only about four or five thousand dollars in total at the time:
“Merle Haggard and his manager, Fuzzy Owens, got me in a poker game and cleaned me out. I had four or five thousand dollars on me, and they won everything.” Waylon implied that he believed there was malicious intent behind Merle and Fuzzy’s game, especially considering what he had just gone through and the low moment he was at in his life and career. He added that Merle was likely in a bad as spot, too, as he was as a struggling artist in Nashville, but he still felt like he was slighted or even taken advantage of in a sense, especially considering how eager they were to take everything he had in terms of money. In Waylon’s mind, they were true friends, and you simply don’t do that to friends, no matter what the deal was before the game:
“They were there to get my money. That was it. I think Merle is a great singer and songwriter, and probably he was in as bad a shape as I was, but we’ve never been close since that night.” While it’s easy, and true, to say that Waylon lost fair and square, and Merle technically did nothing wrong, it sounds like there might be a little more to the background of their relationship and this story as a whole that he left out of his book. He admitted that he felt swindled and slighted by Merle, and he added that he “never forgot” the look on their faces when they took his money and ran:
"I can still remember their faces. When I was broke, they said their goodbyes and left. I never forgot that.” Damn... If only they were both still around to give us a little more insight and background on the whole situation. Clearly I don't really think it was about the money at all, but rather that Waylon felt like Merle kicked him while he was down, so to speak. You can't even really find a photo of them together, which is absolutely wild, considering they had the same friends, worked with a lot of the same people, and were often at the same events for many decades. I don't know of many times, or any times, really, they spoke very ill of each other publicly, but you have to imagine there was some deeper stuff going on with them that we'll likely never know. As a huge fan of classic country, it's mostly just sad, because I can't even imagine how incredible a Merle and Waylon collab would've been... they're two of the best vocalists the genre has ever known. And if you want to hear a little bit more about this story and some other great Waylon tales, make sure you check out this video: https://www.youtube.com/watch?v=TUqOoh6EKTU&t=578s
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