JOINT BASE LEWIS-MCCHORD, Wash. -- Capt. Cassidy Pickrell stood in front of her father with her flight wings in her hand, ready to carry on a legacy three generations strong. She carefully broke the shiny new set of Air Force pilot wings in two and handed the other half to her father, retired Capt. Robert Pickrell, Jr. This gesture honored the man who had once flown before her and always stood beside her.
The “Breaking of the Wings” is a time-honored Air Force tradition. New pilots break their first wings in half, one piece kept for themselves; the other given to someone they deeply respect and trust. The halves are never reunited in life, only in death, a symbol of eternal connection and good fortune in the next life.
For Pickrell, that moment wasn’t just about becoming an Air Force pilot. It was about honoring her family’s dedication to service and carrying a legacy forward.
“Breaking the wings with my dad was an emotional moment,” said Pickrell. “I’m glad there wasn’t a speech afterwards because I don’t think I could’ve said much.”
Capt. Robert Lawrence Pickrell, Jr.’s 11 and a half years of combined active duty and reserve service include flying for the 53rd Weather Reconnaissance Squadron, known as the “Hurricane Hunters” at Keesler Air Force Base, Mississippi. After completing his military career, he transitioned to the commercial aviation sector and now serves as both a pilot and an instructor for Delta Air Lines. His father, Maj. Robert Lawrence Pickrell, Sr., was a World War II test pilot who flew missions for the U.S. Army Air Corps. before embarking on a distinguished 30-year career as a commercial pilot for American Airlines.
From a young age, Pickrell had a passport full of memories, flying and traveling often with her family and close family friends. Air Force pilots filled her world, yet the choice to follow their path was always her own. When someone asked what she wanted to be when she grew up, she never hesitated: “A pilot like my dad—and then the president,” she’d say with a smile. Her closest family and friends had no doubt she could accomplish either goal.
Driven and resilient, Pickrell tackled every season of life with unwavering determination. She fondly recalls her dad’s mantra: “Hard work beats talent when talent doesn’t work hard,” a motto that guided her through every challenge.
Cassidy’s relentless work ethic began in the world of athletics. From a young age, her remarkable talent caught the attention of prestigious institutions, including the U.S. Air Force Academy and UC Irvine, both vying for her as a standout in volleyball and track and field. Cassidy chose UC Irvine, where she took on the role of team captain. Her journey continued at Arizona State University, where she continued to cement her reputation as a true leader by captaining her volleyball team there as well.
Her skill on the court led to recruitment by professional teams in the European leagues. Pickrell’s career took her to Switzerland for her first season, followed by time in Poland, and a return to Switzerland, before concluding with a final season in Germany.
While playing professional volleyball abroad, Pickrell began to reflect on her childhood dream of becoming a pilot. Living overseas deepened her appreciation for her country and inspired a strong desire to pursue her dream of serving as a pilot in the U.S. Air Force.
After returning to the U.S. directly from her time competing on the European professional volleyball circuit, she hit the ground running, dedicating herself to earning her private pilot’s license in preparation for the rigorous Undergraduate Pilot Training program.
Pickrell enlisted the guidance and support of the many Air Force pilots she had grown up with, including her father’s lifelong friends and fellow aviators, Lt. Col. Mark Stevens and Lt. Col. David “Scotty” Dufreche, who flew on many training flights with her while she prepared for the academy.
“Cassidy was an absolute natural,” said Stevens. “She flew multiple hours with me and then for her next set of hours she flew with her uncle Scotty Dufreche, to make sure she liked to go upside down and do loops. She wanted to keep flying all day, he told me he had to tell her to land, because she wore him out.”
In July 2021, Pickrell began her pilot training on the T-6 Texan II alongside her fellow classmates at Vance Air Force Base in Oklahoma. Throughout the rigorous program, she maintained nightly conversations with her father who learned an entirely new planes system publication to help her study. He shared insights and guidance with her as she progressed through each phase of training. Their discussions not only strengthened her skills but also deepened the familial legacy of dedication and service that has shaped her journey.
“Cassidy was such a dedicated student,” said Pickrell, Jr. “She would call me to go over the system of the week or the two systems of the week while she was in pilot training. We would talk through it together, and then the next night I would question her about it to make sure she knew it. She was a self-starter with all her instrument’s training, as well.”
At her March 2022 graduation, Pickrell was honored by her classmates with the Top Wingman Award for her T-6 class. She later received the distinguished Risner Award during her July 2022 graduation upon completing the T-1 class. Both peer-selected honors recognize individuals who demonstrate exceptional leadership and a strong commitment to supporting their fellow students.
“I just always tried to include everyone in everything and took the extra time to help my people when they asked for it,” said Pickrell. “I feel like most of my class was that way though, so it truly was an honor and shock when I was gifted those awards.”
Today, Pickrell pilots the C-17 Globemaster III with the 313th Airlift Squadron at Joint Base Lewis McChord, executing missions that take her to destinations around the world, carrying forward her family’s legacy.