A Catch-up Conversation with Jack Wesselo
Jack, when you grew up in Uxbridge, the town was focused on farming. But you became obsessed with flying. How did that happen? What was the attraction?
I was always fascinated by things that flew. From paper airplanes and kites to the small planes that few out of Greenbank Airfield. My dad would take me to airshows and museums, and my grandma was qualified as a pilot, so I had a lot of support from my family. As fortune would have it, a classmate of mine in elementary school was the son of a helicopter pilot: as soon as I got a ride, I was hooked!
Targeting a career in the air, how did that affect your choices in secondary and post-secondary education? What does a pilot need to know?
Maj. Wesselo in Mali, 2018, with a Chinook in the background.
In high school, I focused on math, physics, and science courses at the advanced levels. For one of my extracurricular activities, I was a member of the Royal Canadian Air Cadet program: this gave me the opportunity to earn flying scholarships, where I gained both my glider pilot and private pilot wings. I could have then directly entered a college aviation program; however, following the encouragement of my parents, I instead decided to study aerospace engineering at Ryerson University. I didn’t decide to join the military directly out of high school (thankfully there was an opportunity to join later), because the military requires all pilots to be officers and all officers must have a post secondary degree, this decision set me along the right path for my future military career.
Why helicopters as opposed to airplanes? And why the military instead of Air Canada, or flying geologists or surveyors into the far north?
Like I said, I got hooked early! Helicopters are truly mechanical marvels. When I was a kid they seemed to be fantastically complex machines operating with fine tolerances and almost impossibly manoeuverable. As a child, observing demonstrations of the Search and Rescue aircraft at the Toronto International Airshow definitely helped further my interest. Comparatively speaking, flying commercial airplanes filled with hundreds of passengers is a huge responsibility: some of the best pilots I know do that every day, but the idea just never really appealed to me. The military was attractive mainly due to the fact that I couldn’t have afforded the cost of flight training on my own! I also didn’t want to be an engineer in a cubicle for the rest of my life; additionally, after the events of 9-11 I felt the civilian aviation path was too tenuous. With my background in the Air Cadets and a strong desire to be of service and to help other people, I joined the military with an initial goal of becoming a search and rescue helicopter pilot.
A military life can be hard on families, and you’ve moved around a lot, and yet you’ve built a happy home. Tell us a little about your wife and kids.
Maj. Wesselo at test pilot school, Maryland, 2023, with a Canadian-made DeHavilland Otter, one of the oldest planes in the U.S. naval fleet.
Heather is a nurse practitioner in primary care and, despite the challenges imposed by military life, she has managed to make a very successful career with a combination of in-person clinical work, online care delivery and teaching at the university level. Our three kids (aged 6, 10 and 12 years) lead busy lives with outdoor sports and extra-curriculars, which require the aid of friends and family as caregivers and drivers, but one of the keys to our family’s success has been Heather’s ability to run the household and her own career when I’m gone. It’s obviously better when I’m home and we can be a team. Of course the kids miss me when I’m away, but without Heather’s strength (and she will also admit, stubborn will) and independence on the home front, I believe I would never have been able to accomplish so much in both my own career and for my life with a family of my own.
Your career has taken you to some dangerous places, like Afghanistan and Mali. What was your role on those assignments?
In Afghanistan I was a First Officer and a brand new Captain, flying the CH146 Griffon in escort and overwatch roles for other helicopters, road convoys, and troops on foot patrols. I was on the first helicopter rotation that Canada contributed to the allied effort in Afghanistan, landing in Kandahar shortly before Christmas 2008. I spent the next four months flying roughly every other day in temperatures from below freezing to over 40C. We flew missions in support of Canadian and American troops in the Panjwai district (which was Canada’s primary area of responsibility), and British troops out of Camp Bastion in Helmand Province.
By the time I went to Mali in 2019, I was qualified on the CH147-F Chinook, had attained the rank of Major, and was deployed in the Aircrew Flight Commander position. I was responsible for all the flight and administrative oversight of the crews flying both Chinook and Griffon helicopters while also performing my duties as a Chinook aircraft commander. The Chinook was configured for medical evacuation to accommodate small medical and force protection teams embarked while the Griffons were once again in the escort role. We were deployed in support of the United Nations Multidimensional Integrated Stabilization Mission in Mali (MINUSMA) from the Gao airfield and we primarily responded to attacks on UN troops. We would occasionally get to conduct missions in support of ground troops or to move cargo around the area, roaming as far as Kidal, Ansongo, and Timbuktu. My team was deployed for eight months and conducted roughly one real-life MEDEVAC response per month, filling the rest of our time with practice exercises with the UN forces and cargo missions.
You just returned from a special course in Maryland, the only Canadian in an exclusive international group. What was that about?
A modern helicopter pilot in the cockpit.
I had the privilege of attending the United States Navy Test Pilot School (USNTPS) as a rotary-wing student of Class 163. It consisted of two months of pre-course training, learning how to fly the UH-60 Black Hawk and the UH-72A Lakota, followed by an intensive 11-month course at Naval Air Station Patuxent River, Maryland. During USNTPS, I primarily flew the Black Hawk and Lakota, but had the chance to conduct brief evaluations of six fixed wing airplanes, from very slow bush planes and gliders to supersonic jets; nine other helicopters, including a Vietnam-era attack helicopter, and two drones. The course had 29 students, with representation from all branches of the US military, as well as students from Australia, Israel, and Italy.
And this summer, you’re off to southern California, on the leading edge of a new military frontier you couldn’t have imagined when you were a kid. And you’re taking the family this time. What will you be doing?
I’ll be a member of what is known as an “integrated test team,” conducting the evaluation of Canada’s newly acquired Remotely Piloted Aircraft System (a.k.a. drones!) as the sole project test pilot. These systems will be used domestically to support the Maritime and Northern surveillance missions, and will have an expeditionary capability (i.e., for defence). It is rare to be entrusted with this kind of responsibility as a brand new tester, but thankfully the rest of the team I’ll be working with is very experienced and will help me through the process!
What advice would you give to a young person considering a career in the military, especially in the Air Force?
It’s worth it! We get to fly amazing machines as part of an incredible team while supporting Canadians domestically and abroad. It’s a very rewarding career with a huge set of benefits, but it also comes with some very real challenges. Don’t worry too much about where you may get posted in your career - each base has its own charm, especially if you’re the type who seeks out friendships, you’ll do just fine.
Photos submitted by Major Jack Wesselo