Damon Brad (Squid) Wintrup

Brad Wintrup began flying with the Royal Canadian Air Force in 1991.

The first half of his career in aviation were spent on Military Jets and the second half on Transport aircraft.

While flying Jets, he amassed over 2000 hours as an A2 Qualified Flying Instructor (QFI) on there Canadair CT114 Tutor aircraft, and, a Standards and Evaluator Pilot (STANEVAL) on exchange with the United States Air Force flying the Cessna T37B Tweety Birds twin engine jet trainer.

He was a QFI and Flight Commander at 2 Canadian Forces Flying Training School (the “Big 2”) in Moose Jaw Saskatchewan where he taught pre-wings pilots the Basic and the Advanced Flying Training Courses. He was a Standards and Pilot (“Snapper”) awarding check rides and qualifications to student and staff QFI pilots. He later worked at the Flying Instructor School (FIS “Vikings”) teaching Winged Pilots how to teach flight training. He also worked at Central Flying School in Winnipeg (CFS “Ravens”) in the Jet Training Standards and Courseware Development section.

Posted to 4 Wing Cold Lake, Squid flew the CF188 Hornet at 410 Tactical Fighter Operational Training Squadron and T33 Silver Star at 419 Combat Support Squadron, and, he served as an Operations Officer during the Kosovo war.

Squid did an exchange flying tour at Randolph Air Force Base, San Antonio Texas with the 559th Flying Training Squadron (“Billy Goats”) flying the Cessna T37B Tweety Bird. Like at FIS, he taught United States Air Force Winged Pilots how to teach Flying to undergraduate USAF Pilot candidates. He becomes a 12th Ops Group, Standards and Evaluator Pilot awarding Flight Instructor categories to USAF Pilots. He left the 559th having achieved every type qualification available on the T37B: Flight Instructor, STANEVAL, Maintenance Test Pilot, 2 ship Formation (Element) Lead, 4 ship (2 Element) Lead, Airshow demonstration pilot, and, 4 ship flyby Lead, and Spin Demonstration Pilot.

After returning to Canada, he completed a “Ground Tour” as Subject Matter Expert in the NATO Flying in Canada (NFTC) Project Office. NFTC trained NATO and allied pilots to Canadian Wings Standard; participating countries included USA, UK, France, Italy, Singapore, Germany, Denmark, Hungary, Saudi Arabia, and Finland.

Returning to flying as a Major, Squid was posted to Canada’s only Tactical Airlift Squadron and also the largest Squadron in the RCAF: 436 (T) Squadron. He served as a CC130 Pilot, Flight Commander and eventually Deputy Squadron Commander. He flew the E and H model “Legacy” Hercules and was one of the first J Model Super Hercules Pilot’s in Canada. After 3 tours in Afghanistan flying the Legacy Herc, he deployed once more as the Task Force Commander (Task Force Canuck) Tactical Airlift Unit. This was the first operational deployment for the new CC130J Super Hercules in the RCAF. He logged over 1500 hours on the CC130 E/H and J model Hercules.

Returning from Kandahar, he was posted to Ottawa to the Canadian Joint Operational Command (CJOC) Headquarters J3 Operations where he served in the operational support team for various operations including Afghanistan, Kosovo, Cypress, and Domestic operations throughout Canada and North America.

He was selected to attend the Joint Command and Staff Program (JCSP) in Toronto where he graduated the program and also achieved a Master Degree in Strategic Studies. He was Promoted to Lieutenant-Colonel and appointed the 25th Commander of 431 (Air Demonstration) Squadron: The Snowbirds. He returned to flying for the last time with the RCAF; back to where he began, flying the venerable CT114 Tutor in Moose Jaw Saskatchewan.

After his Command tour, he returned again to CJOC but this time as Deputy Director of the Joint Air Component Command Element (JACCE) Coordination Liaison Staff where he lead a team of advisors to the Commander CJOC and the Commander Canadian Special Operations Force Command (CANSOFCOM) with “Air Effects” for all Canadian Operations World Wide.

LCol “Squid" Wintrup retired in 2019 after 36 years in the military to return to his passion of flying. His logbook contained entries under the following aircraft types: CT-134 Musketeer, CT114 Tutor, CF188 Hornet, CT33 Silver Star, T37B Tweety Bird, CT145 King Air, CC130E/H Hercules, CC130J Super Hercules.

Brad joined IPA to convert his experience into a Transport Canada civil aviation licenses in 2020. He completed his Flight Instructor Training and was awarded a Class 3 FI rating. He also completed his conversion training to achieve a Commercial Single and Multi Engine Group 1 IFR ratings. He joined IPA initially as a Quality Assurance Manager and then as a Flight Instructor. Soon after he was recruited and approved by Transport Canada as the Director of Flying Operations for Transport Aerien Gatineau (TAG). He flys the PA31-350 Piper Navajo Chieftain as Training Pilot with TAG.

He provides Corporate Flight Services as a Pilot with type ratings on the Bombardier CL30 Challenger 350 and is current on the Bombardier CL64 Challenger 650 aircraft.

For IPA, Brad provides “special” and/or customized instruction on Multi Engine and Instrument Flight Rules ratings. He also provides mentorship and advice for IPA staff and potential clients that require outside the box solutions such as ex-Military pilots seeking civil aviation licenses. He has written a short book: Taking Flight by Damon B Wintrup that briefly highlights differences between civil and military flying training for anyone curious about the differences.

Squid is an active aviation ambassador with over 5000 hours flights time, half of which is as an instructor or evaluator. He is passionate about aviation and enjoys sharing experiences with anyone with a similar interest. He has spoken with Air Cadet Squadrons, high schools assemblies, Defence and Aviation Industry leaders, and Government departments on current and emerging aviation in Canada and around the world.