Flying Fathers, Flying Daughters

By Kevin Cuddihy, Contributing Writer
Capt. Orrett Williams (Air Canada) and F/O Zoey Williams (Air Canada) together on an Air Canada flight deck.

ALPA is rich with second- and even third-generation pilots. Aviation truly does run in the family, with many sons following in the footsteps of their fathers, grandfathers, and other family members.

And while the number of female ALPA members is increasing, women still make up a relatively small percentage of commercial pilots. However, this is changing as more daughters are following their fathers (and mothers) into the profession and onto an airline flight deck.

In celebration of Father’s Day, Air Line Pilot reached out to a handful of father-daughter duos from multiple pilot groups—mainline and regional, large and small, U.S. and Canadian—and asked them to share their special connection, from childhood to the flight deck.

Fathers and Daughters

These fathers and daughters who’ve flown together commercially—and a few “plus ones”—are sharing their stories:

  • Capt. John Asunmaa (Delta) and F/O Krysta Guerin (Delta), plus daughter/sister F/O Danielle Asunmaa (Delta);
  • Capt. Sebastian Léopold (Air Transat) and F/O Stephanie Léopold (Air Transat), plus son/brother F/O Charles-Antoine Léopold (Air Transat);
  • Capt. Ronan O’Donoghue (Alaska) and F/O Jen O’Donoghue (United), who previously flew for Alaska;
  • Capt. Craig Pilloni (United) and F/O Abi Pilloni (United);
  • Capt. Jay Weatherman (Piedmont) and Capt. Jennie Weatherman (Piedmont); and
  • Capt. Orrett Williams (Air Canada) and F/O Zoey Williams (Air Canada).

The Early Years

These daughters experienced an early firsthand look at the world of aviation thanks to their fathers’ careers, getting invaluable exposure to the airline lifestyle.

“My parents took us on a big trip to China when I was 10 years old,” remembers Krysta Guerin. “My dad was a first officer on the B-747, and we got to go onto the flight deck and travel in the upper deck.”

Zoey and Orrett Williams would spend quality time together sharing a love of aviation during her formative years—or so Orrett thought. “My dad would take us plane-watching at Pearson Airport,” explains Zoey. “We’d sit on the hood of our car at Wendy’s in earmuffs watching the planes overhead.” However, her focus wasn’t exactly on aviation. “At the time, I had no interest in airplanes, but we’d get what felt like endless amounts of ice cream, so I was excited to go!”

These daughters also received an early education on the impact a pilot’s schedule can have on family life. For John Asunmaa, that schedule provided a wealth of opportunity. “Time off afforded me more time to be with my kids,” he remembers, “considerably more than most other jobs offered. We used that to our advantage.”

But with that opportunity comes unpredictability at times. “Hats off to their mother and my wife,” says Sebastian Léopold, “for holding the fort together while I was away. It would have been easy for her to complain about the schedule, as it was hard for her to manage work and two kids just 16 months apart, but she took it in stride.”

Capt. John Asunmaa (Delta) with his two daughters, F/O Krysta Guerin (Delta), left, and F/O Danielle Asunmaa (Delta).

Born to Fly

These fathers saw aviation as a potential career option for their daughters but never forced it on them. And while it was love at first sight for some, others early on weren’t set on being a pilot.

Abi Pilloni, however, knew at a young age she was going to become an airline pilot. “I told my parents I was going to be a pilot when I was about six,” she says. “When I turned 10, they took me on a discovery flight for my birthday. I then begged to be taken up every year for my birthday.”

It was a similar story for Jennie Weatherman. “The memory that sticks out to me is Jennie dressing in a pilot’s uniform every single Halloween,” recalls Jay Weatherman. “She also wanted to travel with me on trips. She got a taste of the good—and the bad—of airline life and in the end it’s what she wanted to do.”

“Many pilots grow up with the desire to fly, but that wasn’t the case for me,” admits Zoey Williams. “Learning to fly was a personal challenge for me to face my fears. But through the process of learning to fly and overcoming my fear, I grew to enjoy it.”

“Initially I wanted to be a flight attendant, and I had dad’s full support,” Jen O’Donoghue acknowledges. But that changed after her father gifted her a discovery flight for her 16th birthday. “I remember flying on that discovery flight and absolutely loving it,” she says. “When I landed, I knew without a doubt that I wanted to be a pilot.”

“I graduated from college and worked an office job,” recalls Krysta Guerin, “but I quickly realized an office job wasn’t for me. I enjoyed traveling and seeing the world, which was a deciding factor for becoming a pilot. From the minute I told my dad I wanted to be an airline pilot, he helped me navigate the quickest and most effective route to the majors.”

Capt. Ronan O’Donoghue (Alaska) shares the flight deck with his daughter, F/O Jen O’Donoghue (United), when they both flew for Alaska.

That First Officer Looks Familiar

These fathers and daughters admitted to becoming emotional when they finally realized their ultimate dream of flying together as captain and first officer.

“Several times I had to pinch myself that I was sitting beside my daughter,” notes Ronan O’Donoghue. “There may have been a few sniffles on my part!”

He wasn’t alone. Stephanie Léopold recalls waiting for her father at the airport and watching him approach. “When I saw my dad walking up to the rendezvous point, I noticed he stopped and became filled with emotions,” she says. “Then he pulled out his phone and took photos of me from a distance. I remember him telling almost everyone we saw that I was his daughter.”

“I couldn’t believe I was flying with Krysta, my youngest, at a major airline let alone on an A350 to Seoul, South Korea,” adds John Asunmaa. “I thought of all my retired buddies who never had the chance to do the same with their kids.”

Danielle Asunmaa was hired by Delta in 2022, but she went on maternity leave before having the opportunity to fly with her father; she won’t return until after his upcoming retirement. But with her sister at the same airline, a family flight deck remains a goal. “I was fortunate enough to have watched my sister go through this journey first, and she’s been a mentor to me,” Danielle says. “I’m excited about the possibility of flying with her one day.”

Sebastian Léopold is doubly fortunate as well, with both his daughter and son, Charles-Antoine, joining him at Air Transat. “It’s pretty unreal,” he admits. “I never imagined it would happen. Before they both started flight school, we never really discussed my work. I’ve enjoyed every minute that we’ve spent together working and doing what we love—flying. What a privilege!”

Capt. Sebastian Léopold (Air Transat) and F/O Stephanie Léopold (Air Transat) on their first flight together at their airline.

The Road Less Traveled

Jay and Jennie Weatherman had a unique path to sharing a Piedmont flight deck. Jay spent 25 years flying “Delta’s big jets” before retiring in 2021 as a cancer survivor. “I felt that there were other things I wanted to do in my life,” he says, “and leaving Delta at 55 allowed me to pursue those other interests.”

He didn’t anticipate that interest would include returning to airline flying. But after Jennie was hired at Piedmont, she told him about the company’s direct-entry captain program. He learned more about the airline and its people, “and after some research and thought, I decided to apply and was hired in June 2023.”

It was a race against time for the two, however, as Jennie was set to upgrade to captain in late 2023. Jay completed operating experience training on the E145 a few weeks before his daughter was set to upgrade, and the pair were able to get a few trips in together before she began her training.

“Those were touchstone moments for me,” Jay recalls, “both as a proud father and as a crewmember with my very competent and accomplished daughter. My decision to come out of retirement was 100 percent based on the opportunity to fly with my daughter. I would do it again in a heartbeat.”

Capt. Jennie Weatherman (Piedmont) and Capt. Jay Weatherman (Piedmont) on one of their few flights together before Jennie upgraded to captain.

A Chip Off the Old Block

Many of these fathers acknowledged that their daughters have already surpassed them in certain skills or abilities.

Krysta Asunmaa made the landing in the first commercial flights she flew with her father, and he praised her skill. “Krysta made a great landing,” John remembers. “Then on our third trip together she had me land. Hers were better than mine.”

Craig Pilloni remembers worrying a bit before his first flight with his daughter. “Those thoughts evaporated on the flight deck,” he says. “I knew she’d be smart and knowledgeable, but what truly made me happy was to see what a good and professional aviator she is. Honestly, it’s still sinking in. I changed this kid’s diapers, and now we’re flying a B-737 together!”

At the same time, these daughters recognize and admire their fathers’ skills and contributions to the profession and know that they’re adding to their fathers’ legacies.

“With my dad being at the same company for 26 years, a lot of coworkers ask me if we’re related,” explains Stephanie Léopold. “They think it’s a beautiful story, and I agree. There’s just a little bit of stress that comes with that. I have to keep up his reputation!”

For Jen O’Donoghue, she hopes one day to match her father’s “ability and desire to always help out and lift up others to achieve their goals.” She noted his volunteer work with ALPA, remarking, “He always says to ‘leave things better than you found them,’ and to him that means he wants to leave a lasting impact in all of the work he does.”

ALPA service runs in the Weatherman family as well. Jay is currently a member of the Piedmont Master Executive Council Negotiating Committee, while Jennie is the pilot group’s executive administrator.

‘Girl Dads’ Rock

One common thread throughout these families is that each daughter has felt supported and heard by her father, from childhood through the present.

“When I was a kid, my dad would listen to me talk about anything and everything for hours,” says Abi Pilloni. That continued into adulthood, when she sometimes tagged along with him on trips. “He took me on two ‘breakup’ nonrevving trips and moved me into all my adult apartments,” she remembers. “The breakup trips are particularly great memories. What’s heartache when you can get Cajun food in Louisiana!”

“There really wasn’t a dream or desire that was too grand for us in his eyes,” remembers Jennie Weatherman. “He’s never told me that I’m dreaming too big for whatever I had my sights on. I was never told that I couldn’t do something if I wanted to put the work in.”

Danielle Asunmaa and Krysta Guerin heard the same from their father. “He taught us that we can do anything as long as we work hard and keep trying,” Danielle recalls. Adds her sister, “He taught us to be strong and independent and treated all his kids the same. He supported us and taught us how important it is to work hard to achieve our goals.”

Paying It Forward

These fathers and daughters also shared what advice they’d give to a colleague’s daughter interested in becoming a pilot, given their unique situation and insight.

“Point them in the right direction, mentor them, be honest about the challenges, and provide unwavering support,” suggests Orrett Williams. “Your daughter’s experiences will likely differ from yours, but you can still listen, support, and encourage her.”

Jennie Weatherman recalls the favors her father called in to help guide her in her career and relishes the opportunity to do the same. “When I first started flight training, I pestered my dad into calling every single female pilot he knew so that I could ask them about mentoring me,” she says.

There are a few women Jennie still regularly talks with and asks for advice. “I’d like to pay that forward,” she acknowledges. “I’d happily tell any colleague to have their daughter send me an e-mail so she knows that I’m in her corner and I’m rooting for her.”

Changing Times

The industry these daughters entered is much different from the industry their fathers first experienced, and it will likely change even more as they move throughout their careers.

Ronan O’Donoghue marvels at the speed of his daughter’s career progression. “She achieved flying at a legacy airline at the age of 24, something I could never have imagined,” he says. “I hope her love for the career stays with her and that she takes advantage of all the different types of flying she’ll have the opportunity to experience.”

“There’s never been a better time for women in aviation,” states Craig Pilloni. “Once there are more role models like Abi on the line, I think more girls will see it as a great career path.”

Above all, these fathers have the same hopes that any father would have for their children: happiness.

“I hope Zoey achieves all the dreams and aspirations that she has in aviation and beyond,” says Orrett Williams.

This article was originally published in the June 2024 issue of Air Line Pilot.

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