Hours Before Buddy Holly’s Plane Crashed, His Friend Said Seven Words That Would Haunt Him Forever

The event known as “The Day the Music Died” happened on February 3, 1959. Buddy Holly, J.P. “The Big Bopper” Richardson, Ritchie Valens and their pilot all died when their plane crashed in Iowa. But there were some other musicians who should have been on the aircraft that weren’t. One of them was Waylon Jennings, and before the plane took off he said something that would forever haunt him.

Of course, it’s easy to look back in hindsight and observe the mistakes that led to the plane crash. But Jennings couldn’t possibly have known what would was about to transpire. And it happened while all the musicians in question – Holly, Richardson, Valens, Jennings, plus Carl Bunch, Tommy Allsup, and the band Dion and the Belmonts – were on tour together.

The tour, known as the “Winter Dance Party Tour” was extremely badly planned. The musicians went back and forth, covering hundred of miles of the mid-west to get to their scheduled venues. Indeed, it seemed as if no one had taken into account the amount of traveling required to complete it. Perhaps unsurprisingly, the company that arranged the whole thing, General Artists Corporation, would later receive criticism for this.

ADVERTISEMENT

To make matters worse, the old school buses provided for the tour were in a horrendous state of repair. As a result, they constantly broke down. The vehicles also weren’t designed to endure the terrible weather which the musicians – who all had to travel together – found themselves putting up with.

The snow piled up and up as the musicians traveled and temperatures dropped well below zero. It got so bad that Bunch had to go to hospital for frostbite after the bus broke down yet again. Valens and Richardson unsurprisingly both got the flu. The conditions were utterly miserable for anyone to be traveling in.

ADVERTISEMENT

Eventually, the stars had had enough. On February 2, the musicians played the Surf Ballroom at Iowa’s Clear Lake, an unscheduled stop. From there they were supposed to go on to Moorhead in Minnesota, an almost 400-mile drive. But Holly decided that instead of getting back on the cold and unreliable bus, he and some of the others would take a plane.

ADVERTISEMENT

What happened next decided the course of American music history. There were only so many seats on the plane, so everyone had to decide who was flying and who was getting back on the bus. Valens asked Allsup if they could flip a coin for his seat, and he agreed. The former then “won” the toss.

ADVERTISEMENT

Jennings has always maintained that he was supposed to be on the ill-fated plane. In his 1996 memoir, Waylon: An Autobiography, he wrote, “In between acts, the Big Bopper came up to me. He was a large man, at least 250 pounds, and he could hardly fit, much less sleep, on the seats of the bus.”

ADVERTISEMENT

Richardson then asked Jennings if he could have his seat on the plane. He later recollected in his autobiography, “Heck, I was skinnier’n a rail and could sleep anywhere. I was excited to be on the bus with the other performers. I said sure, ‘but you have to talk with Buddy. If it’s okay with Buddy, it’s okay with me.’” Richardson got the seat.

ADVERTISEMENT

The plane’s pilot, Roger Peterson, was only 21 years old when asked to transport the musicians. In addition, he’d already been working for 17 hours, but, starstruck by Buddy Holly, he agreed to the flight anyway. The craft, a single-engine Beechcraft 35 Bonanza, then took off from Iowa’s Mason City Municipal Airport.

ADVERTISEMENT

At the time the flight was preparing to take off, there were weather warnings in place – but Peterson was never told them. The aircraft barely remained in the air for five minutes before it crashing. It plummeted into a field at 170 miles per hour and all the people inside died instantly. And because of the terrible snow, no one could reach the bodies for hours.

ADVERTISEMENT

Not only was the crash terrible, so, too, was the aftermath. María Elena Santiago-Holly, the star’s wife,  along with his mother, learned of his death via the news media before they were officially informed. Santiago-Holly was pregnant at the time and she later suffered a miscarriage, ascribed at time to the trauma.

ADVERTISEMENT

And there was also a lot of trauma among the friends and loved ones of the crash victims. In 2008 Allsup said in an interview with Darryl Hicks, “It was tragic, that’s for sure. It still bothers me. Just the fact that Ritchie lost his life and I didn’t, you kind of blame yourself in a way. It’s something you think about without wanting to. A lot.”

ADVERTISEMENT

Santiago-Holly also suffered guilt after the accident. In 1959 she told the Lubbock Avalanche-Journal, “I was two weeks pregnant, and I wanted Buddy to stay with me, but he had scheduled that tour. It was the only time I wasn’t with him. And I blame myself because I know that, if only I had gone along, Buddy never would have gotten into that airplane.”

ADVERTISEMENT

Jennings, too, grieved the loss of Holly, who had been both a friend and mentor. The two of them originally met at a restaurant in Lubbock earlier in the decade. Holly then set about making Jennings into a marketable star. He started producing his songs, got him some better clothes and even invited him to play bass on the Winter Dance Party Tour.

ADVERTISEMENT

Holly was a very successful musician at the time he died. He’d had two massive hits with “That’ll Be the Day” and “Peggy Sue.” He was also very popular with the ladies, to the extent that his marriage to Santiago had to be kept secret in order to avoid alienating female fans. She was instead introduced as secretary to his band, The Crickets.

ADVERTISEMENT

The star’s personal life was going well at the time of his death, newlywed and with a baby on the way. But, it seems that Holly’s financial situation wasn’t quite as rosy. According to Jennings, talking to Rolling Stone magazine in 1973, “The only reason Buddy went on that tour was because he was broke. Flat broke. He didn’t want to go, but he had to make some money. I ain’t sayin’ the person’s name that was the reason he was broke.”

ADVERTISEMENT

However, sales of Holly’s records went up considerably after his death. The last song he released, “It Doesn’t Matter Anymore” quickly rose up the charts. After that, his record label released a greatest hits compilation, which also sold very well. Although the musician died too early, it seems that he left an impressive legacy.

ADVERTISEMENT

Of course, the tragedy which killed the three musicians and their pilot affected fans as well. As such, the event itself was later immortalized in the 1971 Don McLean song “American Pie.” It was he who created the phrase “The Day the Music Died” to refer to the plane crash. That title also gave rise to the rumor that the song shared a moniker with the doomed plane. In truth, though, it never had a name.

ADVERTISEMENT

Over the decades, several permanent memorials to the victims of the crash have been built. One, a granite stone bearing their names was unveiled in June 1988 outside the Surf Ballroom, the last place the musicians performed. And close to where the plane crashed, there’s a large pair of glasses representing Buddy Holly and his famous specs.

ADVERTISEMENT

Jennings, of course, never forgot his friend Holly, and even named a son after him. In 1999, not long before his own death, the musician told CMT.com, “If anything I’ve ever done is remembered, part of it is because of Buddy Holly. Buddy was the first guy who had confidence in me. Hell, I had as much star quality as an old shoe. But he really liked me and believed in me.”

ADVERTISEMENT

The musician also wrote about how he couldn’t understand Holly’s interest in him. In in his autobiography, he mused, “[At the time] I was green as a gourd. I hadn’t been anywhere. As a bass player, I must have been terrible.” But the rock star clearly felt that he’d found a kindred spirit in the younger man.

ADVERTISEMENT

As Jennings described in the pages of his book, “[Holly] talked to me all the time about music. I think maybe it was like he was looking in a mirror, reminding himself of the things he had learned along the way. Maybe he could see how hungry I was, and how much I cared about being a singer.”

ADVERTISEMENT

It was because of this close friendship that the last words Jennings said to Holly would haunt him forever. He later wrote in his book about the last conversation with his friend, “The next thing I know, Buddy sends me over to get a couple of hot dogs. He’s sitting there in a cane-bottomed chair, and he’s leaned back against the wall. And he’s laughing.”

ADVERTISEMENT

Then, Jennings recalled, Holly said to him, “You’re not going with me tonight, huh? Did you chicken out?” Jennings said no, he just wanted Richardson to have a seat. The star teased him, “Well, I hope your damn bus freezes up again.” The bass player responded with a joke in kind: “Well, I hope your ol’ plane crashes.”

ADVERTISEMENT

Even though Jennings couldn’t have possibly known what was to come, those words would leave a mark on the rest of his life. In his autobiography he wrote, “That took me a lot of years to get over. I was just a kid, barely 21. I was halfway superstitious, like all Southern people, scared of the devil and scared of God equally.”

ADVERTISEMENT

Though Holly took no offense at the time, Jennings was appalled by his joke. He wrote in the book, “I was afraid somebody was going to find out I said that, and blame me. I knew I said that. I remember Buddy laughing and then heading out to the airport after the show. I was certain I caused it.”

ADVERTISEMENT

Jennings only found out about Holly’s death the morning after it happened. He had slept in the back of the bus all night. When he woke up, the tour manager asked to speak to him. The musician could tell from his tone that something was wrong, so he sent Tommy Allsup to find out what it was. A moment later, he learned his friend was dead.

ADVERTISEMENT

The bass player later mused in his autobiography, “I’ve often wondered if Buddy wasn’t flying that plane. Every time we’d go in a plane in West Texas, the minute we got off the ground, he’d say ‘Let me take the wheel.’ That young pilot – who’s going to say no to Buddy Holly? I don’t know if it makes any difference.”

ADVERTISEMENT

The musician clearly felt guilt over the plane crash and his joke. So much so, in fact, that may have been the tipping point for a period of substance abuse. The world then found out about his drug problem in 1977, when he was arrested at a Nashville studio for “possession of cocaine with intent to distribute.” The charges were dropped but the damage was done.

ADVERTISEMENT

As Jenning’s career progressed, he tried to keep Holly’s memory alive. In 1976 he released the song “Old Friend,” which featured the lyrics, “Was it really years ago/It seems like only yesterday/The last time that I saw/You laugh at me and fly away.” And the album the track appeared on ended up going gold.

ADVERTISEMENT

Later on, Jennings also ended up owning a motorcycle that had once belonged to his old friend. In 1979 the two remaining members of The Crickets – J.I. Allison and Joe B. Mauldin – managed to track down Holly’s 1958 Ariel Cyclone bike. As a birthday surprise, they then placed it inside the musician’s hotel room.

ADVERTISEMENT

Jennings recollected the motorbike story in his autobiography, saying “I walked into my hotel room after the show and saw it sitting there. What else could I do? I swung my leg over it, stomped on the kickstarter, and it burst into roaring life. First kick. It was midnight, and it sounded twice as loud bouncing off the walls of that hotel room. I knew Buddy wouldn’t mind.”

ADVERTISEMENT

Drugs and self-sabotage, however, continued to feature in Jennings’s life, and eventually he had enough. He told People magazine in 1984, “I’d go out and sit by the pool in the dark and think about what it was doing to me, to my people and to my family. It was ridiculous – the money I was spending on cocaine, and what it was doing to my life.”

ADVERTISEMENT

Fortunately, Jennings was eventually able to cut the drugs out of his life. He told People, “I know that I can never even touch it, and I don’t want to. I’m a drug addict, and if I ever do it again I’ll be right back on it. It took me a couple of mornings sitting out by myself in the wilderness to be able to say I was ‘quitting,’ not ‘stopping.’ I wanted to make it for sure.”

ADVERTISEMENT

In Jenning’s later years, he decided to put his family above all else. As a result, he stopped touring in 1997 so he could spend more time with them. He did, however, continue to sing and give occasional concerts. In 2000 he recorded what would transpire to be his last album, and was entered in the Country Music Hall of Fame in 2001. Then, in 2002, he passed away.

ADVERTISEMENT

Unfortunately, the rock ‘n‘ roll lifestyle had damaged Jennings’s health, despite his quitting drugs. In addition to heart problems, he also suffered from diabetes. As a result, in 2000, the musician had an operation to help the circulation in his leg, and the year after that, things got so bad that doctors amputated his foot. When he died of complications from the disease, he was only 64 years old.

ADVERTISEMENT

Many obituaries written for the late singer mentioned his brush with mortality and the tragedy that haunted him. The BBC wrote of his passing, “Waylon Jennings’ life had more than its fair share of triumph, adversity, success and near-death experiences – all of which helped make him a country music legend.”

ADVERTISEMENT

No matter what, though, Jennings always credited Holly with giving him the career he had. In 1994 he spoke to Holly George-Warren for a Rolling Stone magazine piece that ended up unpublished. During the interview, he said, “What I learned from Buddy Holly, if I never learned anything else, was to not compromise your music.”

ADVERTISEMENT

And Jennings also spoke about the plane crash. He reiterated that for a long time he’d blamed himself. The musician said, “I came back feeling really guilty, thinking I had caused it. When you’re 19 you can’t find any other reason for it to happen except that you caused it. You’re alive and they’re dead.” But it wasn’t his fault – it was just a matter of luck.

ADVERTISEMENT
ADVERTISEMENT