Brother & Sister Pilot Southwest Boeing 737 Flight Together

Stories about families sharing the seats in the flight deck tend to pop up from time to time, warming the hearts of our readers who join in on the celebrations. Today, we celebrate the story of a brother and sister pilot duo from Southwest Airlines who flew together within the same airline for the first time last week.

Aviation runs in the family

The brother and sister pilot duo would be Greg and Jennifer Eastom of Southwest Airlines, whereby Greg is currently a First Officer, and Jennifer is an Assistant Chief Pilot. They were inspired into the aviation industry by their father, an electrical engineer at Boeing for over 40 years who worked on aircraft throughout his career.

Apart from constantly being able to accompany their father and probe into the different things he did at work, the siblings’ love for aviation grew as they always went for plane-spotting adventures. Jennifer reminisced about the past by saying:

“As kids, my parents would drive to vista Del Mar so we could see the airplanes from LAX take-off and land while sitting in our station wagon. Our dad’s last airplane was the C-17 which we also got to see some of the proving runs.”

Eventually, the sibling duo made it their childhood dream to operate the flight decks themselves, much to their father’s delight. As Jennifer highlighted, he was excited when both siblings decided to take up aviation. He often cracked jokes about how someone else in the family would finally understand all the aviation acronyms.

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Earning their wings

Jennifer was the first of the duo to get her wings when she graduated from flight school at the University of Dakota. Greg then got motivated to earn his own set of wings after his sister, as he was quoted saying:

“If she can do it, then I can do it too.”

After earning their wings, the siblings progressed in their individual aviation careers with different airlines, each having flown for at least 27 years. At one point, they were even both former instructors at Torrance Airport. And eventually, both siblings met back at Southwest Airlines, where Jennifer has been working for almost 18 years, whereas Greg has been with the low-cost carrier for about seven months.

While Jennifer and Greg achieved their childhood dream of becoming pilots, they still had their siblings’ dream of operating a flight together for the same airline. And since they were now flying for Southwest Airlines, it was just a matter of time before their dream would come true.

Photo: Vincenzo Pace | Simple Flying

Catching a flight together

That dream came through last Wednesday when both siblings were stationed at Los Angeles International Airport, and Jennifer jumped at the chance to fly with her brother. She swung by and picked up Greg from their dad’s house on the way to the airport and then proceeded to fly six legs with him from Los Angeles to Las Vegas, then onward to Sacramento before flying back to Las Vegas to mark the halfway point of their flight together.

The remaining half consisted of a flight from Las Vegas to San Francisco before returning to Las Vegas and finishing off in Phoenix. When asked what it felt like to fly with Greg finally at the same airline, Jennifer celebrated by saying:

“My family is very family-oriented, so flying with Greg at Southwest Airlines was definitely a dream come true. I always hoped we could retire from the same airline, and it seems that this might eventually come true too.”

While the occasion was indeed celebratory, the siblings felt that the only bummer was that their late mother could not witness their moment together on the flight. Still, the siblings knew that deep down, their late mother knew it would happen one day, and it did.

And while their late mother might not have been physically present, she might have been with them spiritually, as when the siblings were flying out of San Francisco, they saw a shooting star. At that moment, Jennifer told Greg that it was their mother’s way of letting them know that she was happy and beyond proud of them and their achievements.