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.”
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.
