Pali Pilot Soars on The Kelly Clarkson Show

Pali senior Cailey Stewart (left) on The Kelly Clarkson Show with her mom (middle left) and two mentors.)

Pali senior Cailey Stewart is $50,000 closer to realizing her dream of becoming a professional pilot. During her Feb. 24 appearance on NBC’s “The Kelly Clarkson Show,” Stewart won a scholarship to the flight school of her choice, courtesy of the Boeing Company and Clarkson’s campaign to support and encourage young Black people striving to break into the least diverse industries. 

Stewart, 18, aims to join the fewer than 150 Black female commercial pilots working in the nation today.

“This season we’ve made a commitment to amplify Black voices, to highlight Black change makers and businesses that elevate their communities,” Clarkson said on the show. “We want to help remove some of the obstacles they face as they shatter those glass ceilings and fulfill their passions.”

Clarkson announced that Stewart will also be taken under the wings of two experienced Black female pilots. Captain Theresa Claiborne, the first Black female Air Force Pilot, and First Officer Beth Powell, a pilot for American Airlines, encourage young Black women to enter the aviation industry through their “Sisters of the Sky” mentorship program.

As part of that initiative, Claiborne and Powell invited Stewart to join them in Miami over the summer for the “Girls Rock Wings” event, an outreach and flight orientation program.

“I can’t wait to go,” Stewart told Clarkson. “I really want to see more Black female pilots. It’s just really inspiring to me. I’m so excited.”

As the daughter of a flight attendant, Stewart has been around planes since she was young. When she was 14, Stewart’s mother took her on a flight to Hawaii, which she said sparked her fascination with planes. 

Stewart flying a plane last year

“I got the chance to be in the cockpit, and I thought it was amazing to see the different buttons that they use,” Stewart said. “I wanted to know how they got this huge plane in the sky.” 

Tragedy struck Stewart in 2017 when her brother Jaylen died, but it hasn’t kept her down. Since his passing, flying has taken on a new meaning for her. 

“I remember doing my [first solo flight] not too long ago, and, honestly, when I had control of the airplane, I felt like he was closer to me,” she said. “I was up there in the sky, in the clouds, so I felt like I was closer to heaven, that he was right there with me.”

Stewart is aiming high, hoping to serve her country and work for an airline. 

“My dream is to become a commercial pilot and to fly C-130s in the Air Force,” Stewart said. 

In pursuit of her goal, Stewart has applied to various flight schools and has already been admitted to seven. However, Stewart has long been aware that a career in aviation carries a heavy financial burden. 

“I’ve been having to apply for a lot of scholarships to pay for these schools because they’re really expensive,” she said. “You’re not only paying for the cost of college, but you’re also paying for your flight license too.”

Now, with a $50,000 scholarship in hand, Stewart is ready for takeoff.