Features

Mother and son pilots fly together in a milestone moment for Alaska Airlines

Jeff Miles fulfilled his lifelong dream last week by joining his mom, Captain Michelle Miles, in the flight deck, making history as Alaska Airlines’ first mother-son pilot team.

Follow Aeronews on Facebook, Twitter, LinkedIn, Bluesky and TikTok

Jeff Miles grew up watching his mom leave for work in her Alaska Airlines pilot’s uniform, never thinking much of it. After all, he thought, doesn’t everyone’s mom fly airplanes for a living? But as Jeff got older, he began to understand how extraordinary his mom’s job was and aspired to one day follow in her footsteps.

That dream came true last week when Jeff, a newly hired first officer for Alaska Airlines, joined his mom, Captain Michelle Miles, in the flight deck of a Boeing 737 to fly from Seattle to Kahului, Maui.


As Jeff prepared for the flight, he could hardly contain his excitement. “I’ve waited 27 years for this moment,” he said while taking his seat beside his mom. Together, Jeff and Michelle made history as Alaska Airlines’ first-ever mother-son pilot team in its 90-plus years.

A chance bit of serendipity for an airline with approximately 3,000 pilots and 1,400 daily flights that these two would end up paired in the flight deck? Not exactly. The milestone involved schedule juggling and logistics assistance from Alaska’s chief pilot’s office, but the effort was for good reason. Michelle, a 37-year captain retiring this fall, and Jeff had talked for months about continuing a family tradition that began nearly three decades ago.


Flashback to 29 years ago, almost to the day of Jeff and Michelle’s flight, Michelle found herself in the pilot’s seat beside her father, Capt. Richard “Ski” Olsonoski. Back then, the two Alaska Airlines pilots had longed to fly together and eventually had the opportunity to team up during a “Take Your Daughter to Work Day” celebration.

Growing up Alaska Airlines

You could say Jeff has jet fuel in his blood. Grandfather Ski, a retired Navy pilot, joined Alaska Airlines in 1981. In his grandson’s eyes, he was larger than life. “I’ll always think him in his leather bomber jacket and his crush cap. His look just embodied ‘pilot’ to me,” Jeff explained.


As a young boy, Jeff often played fighter pilot while wearing his grandfather’s old Navy flight helmet (despite his mom’s attempts to hide the dusty, dirty helmet) and commanding his squadron of buddies. “Little me would often just stare at that helmet and imagine what it would be like to soar through the air, hearing the sound of the wind and engines,” Jeff said.

Michelle started flying at age 16, buoyed by her dad’s example. She got her private pilot’s license at 17, attended Embry-Riddle Aeronautical University and went on to serve in the U.S. Air Force. She joined Alaska Airlines in 1988 as its 17th female pilot – and the first with a military background. She continued to serve in the military reserves during her tenue at Alaska, flying C-141 cargo planes during the Gulf War.