Something special happened in the skies last week.
For the first time in Alaska Airlines’ 90+ year history, a mother and her son flew a commercial plane together as the pilot team. Captain Michelle Miles and First Officer Jeff Miles shared the cockpit on a flight from Seattle to Maui, marking a heartwarming—and historic—moment for both their family and the airline.
A Dream Come True for Jeff
Jeff Miles grew up watching his mom head off to work in her pilot uniform. As a kid, he didn’t think much of it. “Doesn’t everyone’s mom fly airplanes?” he once thought.
But as he got older, Jeff began to realize just how incredible his mom’s job was. He started dreaming of becoming a pilot too—and not just any pilot. He wanted to sit beside his mom in the cockpit one day.
That dream became reality in May 2025, when Jeff, now a first officer at Alaska Airlines, joined his mom Michelle on the flight deck of a Boeing 737. Their destination? Kahului, Maui—a beautiful spot to make aviation history.
A Carefully Planned Milestone
With nearly 3,000 pilots and over 1,400 flights each day, Alaska Airlines doesn’t normally schedule family members to fly together. But this wasn’t just any flight.
Michelle is retiring later this year after nearly 37 years with the airline. So, with help from the airline’s chief pilot team, schedules were adjusted to make this special flight possible. It wasn’t random—it was something the Miles family had hoped for and planned for months.
And it was worth it.
Flying Runs in the Family
Michelle Miles is no ordinary pilot. She started flying at age 16, earned her private license at 17, and later joined the U.S. Air Force, flying large cargo planes during the Gulf War.
She became Alaska Airlines’ 17th female pilot in 1988—and the first one with military experience. At the time, it was rare to see women flying for major airlines, but Michelle helped pave the way.
Michelle also followed in the footsteps of her own father, Captain Richard “Ski” Olsonoski, who joined Alaska Airlines in 1981 after serving in the Navy. In fact, 29 years ago, Michelle flew alongside her dad during a special “Take Your Daughter to Work Day” flight—an unforgettable memory she’s carried with her ever since.
Now, she’s had the chance to pass that moment on.
Jeff’s Journey to the Cockpit
Jeff didn’t just get the job because of his mom. He worked hard to get there.
He studied aviation at Big Bend Community College in Washington and later worked as a flight instructor. He then flew regional jets for SkyWest before finally being hired by Alaska Airlines in July 2023.
Michelle always supported his dream. “She was always patient,” Jeff said. “Giving me the right nudges to get to where I am now.”
The Big Day
On the day of the flight, Jeff couldn’t stop smiling. “I’ve waited 27 years for this moment,” he said before takeoff.
Passengers were told about the historic moment during the pre-flight announcements—and many clapped and cheered. Imagine sitting on your flight and learning the pilots are a mom and her son!
Michelle and Jeff flew smoothly from Seattle to Maui, each taking a turn at the controls. Passengers may not have noticed anything different during the flight, but for the crew—and the family—it was unforgettable.
At the end of the flight, Jeff stood at the cockpit door, greeting passengers and posing for photos. Everyone could feel that this wasn’t just any flight—it was a once-in-a-lifetime moment.
@alaskaair“They say you don’t get to meet your heroes, but I’ve known mine since birth.” First Officer Jeff Miles on his mom, Capt. Michelle Miles. From all of us at Alaska Airlines, Happy Mother’s Day. 💙✈️
More Than Just a Feel-Good Story
This story is heartwarming, but it also highlights something important.
Even today, women make up only about 6% of airline pilots in the U.S. Michelle was one of the early pioneers at Alaska Airlines, and her success—and now her son’s—sends a strong message: the skies are open to everyone.
It also shows how aviation can run in families. Just like Michelle followed her dad into the cockpit, Jeff is now following his mom. And the tradition continues—Michelle’s other son and his wife are also airline pilots!
Saying Goodbye, and Looking Ahead
Michelle plans to retire this fall, ending an incredible career. For her, this flight with Jeff was the perfect way to say goodbye.
“I can’t really put into words what this means to me,” she said. “It’s all come full circle since flying with my dad.”
Jeff, just starting his own journey with the airline, summed it up beautifully in the official Alaska Airlines video:
“They say you don’t get to meet your heroes,” he said. “But I’ve known mine since I was born.”
Final Thoughts
The skies are full of amazing stories—but some, like this one, really stick with you.
Alaska Airlines’ first mother-son pilot team didn’t just complete a flight from Seattle to Maui. They made history, honored their family legacy, and reminded us that dreams really can come true—even at 35,000 feet.
