Sweet: Mother and Son Pilots Fly Together at Alaska Airlines

by Anthony Losanno

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Alaska Mother and Son Pilots 2

Happy Mother’s Day to all who are celebrating today. Alaska Airlines has shared the rather touching story of a real-life mother and son who are both pilots for the airline. They recently flew together and became the first mother-son pilot team operating together for Alaska Airlines.

Captain Michelle Miles and her son, Jeff, flew a Boeing 737 for the first time as a team last week between Seattle-Tacoma International Airport (SEA) and Maui’s Kahului Airport (OGG). Jeff grew up watching his mom fly for the airline and wanted to become a pilot himself. The new hire for the airline is following in his mom’s footsteps and got lucky being paired with her. Alaska has around 3,000 pilots and 1,400 daily flights. The odds were definitely not in their favor of being scheduled together, but somehow they managed to share a cockpit. Michelle has been flying for 37 years and is preparing for retirement this fall while Jeff is just starting his career as a first officer. She joined Alaska Airlines in 1988 as its 17th female pilot. She’s also the first with a military background.

Flying runs in the family (along with luck) as Captain Michelle Miles got to fly with her father, Captain Richard “Ski” Olsonoski, around 29 years ago. Captain Olsonoski joined Alaska Airlines in 1981 as part of the Jet America merger. He was able to fly with his daughter as part of a “Take Your Daughter to Work Day” celebration. Now, a third generation of commercial pilot has taken to the skies in Jeff.

Alaska Mother and Son Pilots 1

Captain Michelle Miles shared:

Serving as a co-pilot for my dad was one of the highlights of my career. And now, to repeat the experience with my son – well, that’s about as good as it gets.”

Anthony’s Take: What a sweet story. Flying definitely runs in this family’s bloodline.

(Image Credits: Alaska Airlines.)

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1 comment

Susan May 12, 2025 - 3:16 am

The MILES family! I mean, you can’t make that up! So sweet, though!

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