Here’s a Mother’s Day story that will be sure to fill your heart. Jeff Miles, a newly hired first officer for Alaska Airlines, recently joined his mother, Captain Michelle Miles, in the flight deck of a Boeing 737 to fly from Seattle to Kahului, Maui. Together, they became Alaska Airlines’ first-ever mother-son pilot team in the airline’s 90-plus-year history.
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The milestone (video embedded above) was obviously a special one, not just for Jeff and Michelle, but also for the airline, which operates approximately 3,000 pilots and 1,400 daily flights. The duo’s historic flight was made possible through careful scheduling and logistics assistance from Alaska Airlines’ chief pilot’s office.
For Jeff, this moment had been nearly three decades in the making. “I’ve waited 27 years for this moment,” he said. His journey to this point had been shaped by years of inspiration, encouragement and family tradition.
What’s even more amazing is that the Miles family’s aviation story goes back further, with Michelle’s own aviation legacy intertwined with that of her father, Capt. Richard “Ski” Olsonoski. Nearly 29 years ago, Michelle had the chance to fly with her dad on a “Take Your Daughter to Work Day,” an experience she cherishes to this day. Michelle’s father, a retired Navy pilot, joined Alaska Airlines in 1981, setting the stage for a family deeply embedded in aviation.
Growing up with an aviator grandfather and a pioneering mom, Jeff was immersed in the world of flying from a young age. “I’ll always think of him in his leather bomber jacket and crush cap. His look just embodied ‘pilot’ to me,” Jeff recalled fondly of his grandfather, who had a lasting impact on his own aspirations. As a child, Jeff would often wear his grandfather’s old Navy flight helmet and imagine soaring through the sky, feeling the wind and hearing the hum of the engines.
Michelle’s journey into aviation began early as well. Inspired by her father, she earned her private pilot’s license at 17, went on to study at Embry-Riddle Aeronautical University and served in the U.S. Air Force. In 1988, she joined Alaska Airlines as its 17th female pilot and the first with a military background. During her tenure at Alaska, she flew C-141 cargo planes during the Gulf War while serving in the military reserves.
For Jeff, the dream of flying only grew stronger as he watched his mother’s career unfold. With her encouragement, Jeff pursued his own aviation career, attending Big Bend Community College and later working as a flight instructor. After a stint at SkyWest Airlines, Jeff finally received the call he had been waiting for and joined Alaska Airlines in July 2023.
For Michelle, watching her children follow in her aviation footsteps has been a profound joy. In addition to Jeff, her older son and daughter-in-law also pursued careers as pilots for other airlines. Michelle, who is preparing for her retirement this fall after 37 years with Alaska Airlines, reflected on the remarkable journey she has had.
“I can’t really put into words what this all means to me. It’s all come full circle since flying with my dad,” Michelle shared. “My career at Alaska Airlines has been an incredible experience.”
For Jeff, the flight with his mom was a dream come true, an experience that epitomized his lifelong ambition to follow in the footsteps of the heroes who raised him. “They say you don’t get to meet your heroes,” he said, “but I’ve known mine since I was born.”
This historic flight not only marks a family milestone but also highlights the deep connections and bonds that shape the aviation world, proving that for some families, flying is more than just a career … it’s a legacy.
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