First Officer Jeff Miles realized a lifelong dream when he joined his mother, Captain Michelle Miles, in the cockpit of an Alaska Airlines flight from Seattle to Kahului, Maui. This marked a historic moment as they became the first mother-son pilot team for the airline.
Jeff grew up watching his mother work as an Alaska Airlines pilot and aspired to follow her path. “I’ve waited 27 years for this moment,” he said before taking his seat next to her on the Boeing 737.
This milestone was not left to chance. With around 3,000 pilots and 1,400 daily flights, arranging this pairing required careful planning by Alaska’s chief pilot’s office. Michelle is set to retire soon after a 37-year career with the airline. She previously flew alongside her father, Capt. Richard “Ski” Olsonoski, nearly three decades ago during a “Take Your Daughter to Work Day.”
“Serving as a co-pilot for my dad was one of the highlights of my career,” Michelle reflected. “And now, to repeat the experience with my son – well, that’s about as good as it gets.”
Jeff attributes much of his passion for flying to both his grandfather and mother. His grandfather Ski joined Alaska Airlines in 1981 after serving as a Navy pilot. Jeff fondly remembers playing fighter pilot with Ski’s old Navy helmet.
Michelle began flying at age 16 and obtained her private pilot’s license at 17 before attending Embry-Riddle Aeronautical University and serving in the U.S. Air Force. She joined Alaska Airlines in 1988 as its first female military background pilot.
Unlike many childhood dreams that fade over time, Jeff’s desire to fly strengthened with encouragement from his mother. “She knew from the start how much I wanted to fly,” Jeff said.
After completing an aviation program at Big Bend Community College and working as a flight instructor, Jeff flew for SkyWest until joining Alaska Airlines in July 2023.
Michelle’s older son and daughter-in-law are also pilots for other airlines, adding further pride for her family.
Reflecting on her career and family legacy at Alaska Airlines, Michelle expressed gratitude: “It’s all come full circle since flying with my dad.”
For Jeff, sharing this flight with his mom was fulfilling a lifelong ambition: “They say you don’t get to meet your heroes,” he noted, “but I’ve known mine since I was born.”
