There’s no question that trying to make it in the music industry can be absolutely brutal.
And back in the 1960’s, when Waylon Jennings was first starting out in country music, he was barely scraping by and doing whatever he could to get to the next show and at least break even.
Unfortunately, that hard living resulted in a drug addition which he was very open about later in his life. And the rat race of doing whatever it took to get to the next show eventually resulted in tragedy on February 9th, 1969, when one of his band members was killed en route to a show in Illinois.
He explained it all in his 1996 book Waylon: An Autobiography, as his band members were a couple hours ahead of him driving a pickup to get to their next gig when they slipped on black ice:
“On February 9th, 1969, the band was heading to Peoria, Illinois riding in a pickup that had a sleeper stacked on top of it. You could rest in the back, and one person could fit cross wise over the top of the truck cab in a specially made bunk.
I had ordered a blue bird bus from down in Georgia, but it hadn’t been delivered yet. It was to be my first new bus. Ritchie was in the front, and had to let Jimmy Gray start driving.
Outside of Bloomington, on I-50 on the way to Peoria, they came to an old steel bridge over Kickapoo Creek.”
Seeing as they were in the middle of winter in Illinois, there was ice and snow everywhere, and the truck happened slip on some and started spinning:
“It was icy and snowy, and they had to make a sharp right turn. As they slipped on the black ice, they truck shimmied over and leaned a little bit to the side.
Walter Walter ‘Chuck’ Conway, a bass player who had joined me just 11 days before, was asleep in the back compartment over the truck cab.
The poor guy never knew what hit him. The pickup made the turn untouched and kept going, but the bridge clipped the sleeper, shattering it and shearing off the alcove.
Chuck fell plum in the river. Ritchie ran and jumped in after him, but he was too late. They said there wasn’t a bone in his head that wasn’t broken, and he died at the scene.”
Another band member, Stew “Allen” Punsky, a keyboard player, was also badly hurt, and Waylon says he was about an hour or two behind them driving a Cadillac.
When he came up on the scene, he was devastated:
“When I came on the scene, it scared me to death.
The police found pot in the pickup, but when I went down to the hospital, those cops showed me the bag of marijuana and said ‘Waylon, you’ve got enough problems. We’re throwing this away.’”
An absolutely tragic night for Waylon and his surviving band members, but they plugged ahead to their show nonetheless:
“It scared me, made me feel responsible, even though there was nothing I could’ve done.
We played the date using Hank Snow’s bass player, and I was just wobbling around on pills and drunk.”
Not long after that horrific incident, Waylon sat down for a poker game with Merle Haggard and Merle’s manager, Fuzzy Owens.
Waylon had 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.
And we could argue whether Merle or Waylon were both right or wrong all day long, considering Waylon was the one who bet all of that money knowing good and well he could lose it all, but it sounds like what hurt him so deeply was the principle behind what they did.
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.”
If only they were both still around to give us a little more insight and background on the whole situation.
From just hearing Waylon’s side, though, it sounds like he feels as though Merle kicked him while he was already down pretty bad, and I imagine that’s what bothered him so much about what happened.
I don’t really think it was about the money at all.
And though they certainly ran in the same circles in their music careers, and clearly both became respective legends in the genre, they never did much in terms of collaborating on music, likely because Waylon distanced himself after this incident which happened so early on.
They were both great friends with Johnny Cash and Willie Nelson, but that’s about as far as the extent of their interaction ever went.
It’s hard to even 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: