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William Roberts Wilsey

“She told me I couldn’t skydive because it was too expensive, and I told her what if I made it pay for itself?”

William Roberts Wilsey poses in the riggers loft at Skydive Chicago

William Roberts Wilsey didn’t begin his skydiving career like most. Commonly, we see new jumpers beginning their career around the ages of 18 – 24, wide eyed and fearless. Of those who enter the sport, Rob (as we know him) had an entire life before ever thinking of strapping a rig to his back and jumping out of an airplane. “I was 38, when skydiving found me, a “poor construction worker with two young children and a beautiful wife.” 

Born in Frankfort, Germany, Rob would live in 9 different countries before graduating high school in New Deli where he traveled through India and Nepal. Growing up in 3rd world countries, Rob has a deep appreciation for all of the good there is in the world. “My experience of growing up in those countries has made me a better person by far.” So it makes sense that seeing and interacting with an international crowd who are more open and globally minded is just one thing that attracts him to the sport. 

Getting his start at Skydive Orange, Virginia in ’98, and earning his riggers ticket in 2000, Rob immediately took to the gear of the sport as it reminded and felt most familiar to his previous career as a lineman and construction worker. “Coming out of a safety culture already, doing my own rigging, working with my own harnesses in the line-work industry, and doing a lot of rock climbing locally, it just seemed natural that I do these things. I was 38 when I got into skydiving and immediately started packing parachutes and packed as if I were a 16 year old, made it my life, my goal.” Originally, packing paid for Rob’s static line and AFF course, until “it turned profitable and turned itself into an income just by working hard and being there all the time, unexpectedly becoming fruitful.”

Just a few years in, Rob went on a hiatus from skydiving. “Over the course of 5 years I worked my way up to assistant supervisor on job site with 100’s of homes. Realized I didn’t like it and came back to skydiving.” In 2008 as he transitioned away from this career, he balanced construction on the weekdays and skydiving on the weekends continuing to pack his own reserve with his ticket, “then of course people see you doing things and they’re like, ‘hey you want to do me, too?’ and it blossomed into this beautiful career I have now.” It wasn’t long until Rob had made a name for himself at Skydive Orange. “I ended up actually sort of taking over the packing floor at Orange, and getting most of the rigging, doing the schools rigging, yeah just went crazy with it, loved it.”

With the passion and drive, a person can learn anything they want to, so how did he learn his skills as a rigger starting out? “By attaching myself to the hip of every rigger I could find, by pissing them off, by getting in the way, by touching things, by asking stupid questions and smart questions. Just being there every time something was happing so that I could see it, maybe touch it, maybe get involved. I put myself in the right place, with the right attitude to learn.” So what does Rob enjoy most about spending time in the loft? “Coming up with a solution for a problem with gear, whether it’s figuring out how to patch that hole or how to get to it and make it work on the machine, it’s always the challenge.”

When not in the loft, you’ll find Rob on the water, kayaking up and down the river, enjoying all that nature has to offer. One of his winter goals this year is to make it down to see his friend in Oklahoma in order to put his paddle in the Gulf and say “I did that!” Rob also enjoys a bit of light anthropology, studying towns and the infrastructure that allows them to exist. He enjoys old cobblestone roads and the architecture of the homes and buildings that accompany them.

22 years, and 1,200 skydives later, Rob loves the sport just as much as day one. He’s experienced a lot of challenges, surprises, and has memories he will cherish forever. He introduced his son, Daniel Wilsey to the sport and “lives vicariously through him.” “Stoked to see where he’s at now, being a skydiving instructor and being able to share the wealth of info and skill he has, it’s sick, insane, stupid! I’m just excited for everything he’s doing and is able to do. Again, vicariously through him.” When asked what the most reward part of rigging is for Rob, had the following to say. “Knowing that people that I do this for have the ability to do it again tomorrow, even though something may go wrong today, I’m going to give them every opportunity to come back tomorrow and to do it. And when that does happen, that’s my feel good, that’s when I know I’m accomplishing my mission.”

When asked for advice for all jumpers, here are just a couple things he had to share:

Best advice to a skydiver for safety:

“Look to your known true quality peers, people who have already been there. Use those resources, they will keep you safe. Your instructors, your LO’s, 10,000 jump wonders, they’ve been there, they’ve seen the problems and probably had one or two”

How to get longevity out of your gear:

“Treat it like its your puppy. Love it care for it, keep it in the right place.” “Know it, understand it, pull your handles when you get your repack”

William Roberts Wilsey’s perspective on the community:

“You can’t make any of us do anything, that’s why we do this. But you try real hard, you love real hard, you hope real hard that the advice will be taken and they adhere to it. And if they don’t you be there for them after the fact as well.”