Ray Henderson Shares Story Behind Annual Skydive Tradition

by | Mar 2024

Ray Henderson

Ray Henderson. Photo: Chris Emeott

Ray Henderson finally retired at age 85, just in time to start skydiving.

Every year, more than half a million people in the United States skydive for the first time. These jumps are usually tandem free fall with an instructor who is attached to the same parachute system, or accelerated free fall, where instructors accompany the diver in free fall while holding on to the diver’s harness, according to the United States Parachute Organization.

Ray Henderson* is getting ready for his third tandem jump in June. He was 90 when he took his first skydive at 13,000 feet (or 2 1/2 miles off the ground) in 2018 at Skydive Twin Cities in Baldwin, Wisconsin. “These parachutes are called canopies because they’re rectangular shaped,” the Maple Grove resident says, pointing at a photo from his skydive experiences. “They’ve got more control [than a parachute]. The trainer let me steer it the first time I jumped.” The second time, shortly after he turned 95, on the day of his beloved late wife, June’s, birthday, he did it again. “My knees were bothering me, so they got a guy and helped me up the steps [of the plane],” he says. “Believe it or not, we rolled out of the door together. I was very tightly strapped to the jump instructor. You free fall for the first half, and you get going pretty fast. There’s a break mechanism above our head, which collapses the chute, and then you just touch the ground.” He describes the landing quietly, reflecting on the peace he felt.

Henderson’s skydiving activity may make him seem like a bit of a daredevil, but when asked why he started jumping from a plane when he turned 90, he says nonchalantly, “It was the ‘Mount Everest’ thing to do, because it’s there,” he says. “I got tired of hearing about [former President] George Bush. They always talk about how he jumped when he was 90. And I do it for my wife, June, because she would do it if she was here.” Henderson’s wife died from cancer 20 years ago.

His path to skydiving likely began shortly after meeting his future bride at North High School in Minneapolis. “I went right into the military after graduation,” he says. He learned to fly in the United States Navy, where he says his instructor tested him with a power stall and an upside-down tailspin. “Before he flipped [the plane] over, I had my hand on my rip cord for the parachute and a seat belt across my lap,” Henderson says. “As I was holding on, I saw him look at me in the rearview mirror, and he asked me when we landed why I was holding on to my rip cord, so I told him I didn’t trust my seatbelt.” He says it was important not to insinuate it was the pilot’s flying skills that were the real reason for his nerves.

But flying in the Navy gave Henderson confidence about heights. “Looking back, I sat on a parachute in the military but never used one,” he says. And he jumped into life after that, spending 48 1/2 years married to June. They raised five children together. “I still think of her when I hear the words from the Elvis version of the song Are You Lonesome Tonight? It was really popular when we met and reminds me of the two of us,” he says.

Freefall in the Twin Cities

Skydive Twin Cities, where the Navy veteran completed both jumps, was founded in 1975. The Drop Zone flies Cessna Supervan 900 planes holds 18 skydivers, and are fast climbing, turbine, skydiving aircrafts. The plane takes off from Skydive’s privately owned airport, so jumpers touch down on even, uninterrupted land. Owner Kerry McCauley says each jumping rig is equipped with an automatic activation device, known as an AAD, which is designed to automatically activate the parachute if a jumper has any trouble. “Tandem is usually the best, first way to do a first jump,” Mccauley says. “We give you a short briefing on what you need to do and you sign some waivers. That’s what’s great about tandem jumping. You can just come in and get out there and have fun.”

McCauley says those wishing to jump must be at least 18 years old and a note from a doctor is required if a person is taking medications or has had medical conditions including heart disease, joint dislocation, blood pressure or other issues. These are all issues Henderson has experienced—he says he’s had a heart valve and a hip replacement, and his doctor says he has no cartilage in either knee. “I don’t yield to my problems,” he says as he points to a walker in the corner of the room, visibly brushing off any sign of worry.

“It’s really cool seeing older people jump,” McCauley says. “We get a fair amount of people in their 80s, maybe one 90-year-old each year. I jumped with Ray when he was 90 and my son, Connor, was with him this last time. Our oldest jumper here was 98. So, Ray’s got a few years to pass him up.”

At the other end of the spectrum, minimum age is a requirement, so Henderson says he’s going to need to continue jumping until he’s at least 106. That’s when his granddaughter, Gracie June, turns 18. “She wants to do it already,” Henderson, a grandpa of seven and great grandpa of three more, says of Grace’s goal to skydive too. “She’s really a sharpie. She could do it sooner I bet; she’s a really athletic person, just like my wife was. Gracie and I are making our plans to skydive together.”

His face lights up as he sees his granddaughter’s picture on his phone. “Do you look at your door, and imagine me there,” he sings out loud, “thinking about June,” he says, and begins to talk about driving ranges, putting greens and another way he stays active while spending time with the younger generations.

Skydive Twin Cities
2606 County Road J, Baldwin, Wisconsin; 715.684.3416

*Henderson’s family informed Maple Grove Magazine that Ray Henderson passed away in late February. We are grateful and honored to share his story with our readers.


Recent Stories

Pin It on Pinterest

Share This