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Alaska Achieves Milestone With First Mother-Son Pilot Pairing

Capt. Michelle Miles and First Officer Jeff Miles share the flight deck, continuing a three-generation aviation legacy.

Mother-daughter pilot team

Jeff and Michelle Miles (Photo: Alaska Airlines)

In a historic moment for Alaska Airlines just ahead of Mother’s Day, Capt. Michelle Miles and her son, First Officer Jeff Miles, recently shared the flight deck, marking the airline’s first-ever mother-son pilot team. The duo operated a Boeing 737 flight last week from Seattle to Kahului, a city on the Hawaiian island of Maui, fulfilling a lifelong dream for Jeff and continuing a family legacy spanning three generations.

“I’ve waited 27 years for this moment,” Jeff said as he prepared to sit beside his mother in the cockpit.

Not a Coincidence

The pairing was not coincidental; it involved coordinated efforts from Alaska’s chief pilot’s office to align their schedules, the carrier said, ensuring this milestone could be achieved before Michelle’s planned retirement this fall after 37 years of service.

Michelle’s aviation journey was inspired by her father, Capt. Richard “Ski” Olsonoski, a retired Navy pilot who joined Alaska in 1981. Reflecting on her career, Michelle recalled the moment:

“Serving as a co-pilot for my dad was one of the highlights of my career,” she said. “And now, to repeat the experience with my son — well, that’s about as good as it gets.”

Article on father-daughter flight with Alaska (Photo: Alaska Airlines)

Jeff’s passion for flying was evident from a young age. He often donned his grandfather’s old Navy flight helmet and imagined himself soaring through the skies.

Michelle, who began flying at 16 and earned her private pilot’s license at 17, served in the U.S. Air Force before joining Alaska in 1988 as its 17th female pilot and the first with a military background.

After attending Big Bend Community College in Washington, Jeff started his airline flying career at SkyWest. He later joined Alaska in July 2023. Along with Jeff, Michelle’s older son and daughter-in-law are also pilots for other airlines.

Ryan Ewing
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  • Ryan Ewing

    Ryan founded AirlineGeeks.com back in February 2013 and has amassed considerable experience in the aviation sector. His work has been featured in several publications and news outlets, including CNN, WJLA, CNET, and Business Insider. During his time in the industry, he's worked in roles pertaining to airport/airline operations while holding a B.S. in Air Transportation Management from Arizona State University along with an MBA. Ryan has experience in several facets of the industry from behind the yoke of a Cessna 172 to interviewing airline industry executives. Ryan works for AirlineGeeks' owner FLYING Media, spearheading coverage in the commercial aviation space.

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