When your hero is Mom: 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.

eff 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.

Take Your Kid to Work Day
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 that Jeff has jet fuel in his blood. Grandfather Ski, a retired Navy pilot, joined Alaska Airlines in 1981 as part of the Jet America merger. 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.

Jeff attended Big Bend Community College in Moses Lake, Washington, where he completed an aviation program and later worked as a flight instructor while earning his four-year degree. He initially flew for SkyWest until he received the call he’d been waiting for and joined Alaska Airlines in July 2023.

In addition to Jeff, Michelle’s older son and daughter-in-law are pilots for other airlines. For Michelle and her husband, an engineer and stay-at-home dad, seeing their children soar in their careers has been a profound joy.

“I can’t really put into words what this all means to me. It’s all come full circle since flying with my dad. My career at Alaska Airlines has been an incredible experience,” Michelle said.

For Jeff, who felt like he’d been preparing for this day his entire life, the flight with his mom was a dream come true. “They say you don’t get to meet your heroes,” he said, “but I’ve known mine since I was born.”