Bob Cooper honored for 50 years of flying

Milton resident receives Master Pilot Award from FAA
July 18, 2023

After 50 years of flying, Bob Cooper knows a thing or two about aviation. 

Although the Milton-area resident never flew regularly for a job, he’s amassed 2,900 flight hours over the last five decades. Because of his dedication to flying and doing it safely, Cooper was recently honored with the Wright Brothers Master Pilot Award from the Federal Aviation Administration.

Fellow award recipient and neighbor John Chirtea hosted a brief ceremony for Cooper’s family, friends and neighbors July 1 in the hangar at his home at Eagle Crest Aerodome near Milton. Cooper’s wife Janet; three sons, Steve, Dave and Rob, and their wives; and 11 grandchildren were on hand to celebrate the award. 

Cooper’s aviation story began when he was a teenager. He traveled with a church youth group to Hershey Park in Pennsylvania, where he saw a sign offering $5 airplane rides at the local airport. That’s all it took to hook him. 

“I thought it was pretty neat,” he said. “I thought, I gotta learn how to do this. That started my love of aviation.” 

After graduating high school in Maryland, Cooper attended Bob Jones University in Greenville, S.C. The school didn’t have an aviation program, but Cooper was able to take lessons at the Greenville airport. He completed his first solo flight from that airport May 1, 1973. It’s from the first solo flight that the FAA tracks flight hours. 

After college, Cooper returned to Maryland, where he joined the Prince George’s County Police Department. Again, aviation was not an option because the department’s only aircraft, a helicopter, had crashed a few years earlier and the department was not replacing it. There wasn’t an aviation unit the entire time he worked for the department, but shortly after he retired, it added two helicopters. 

Cooper and his wife married in 1978. For the honeymoon, they found a place in the Poconos that had its own runway. The day after their wedding, they flew in high winds to the Pennsylvania mountains to celebrate their nuptials. About six months later, they flew to the Bahamas. It is still the only time Cooper flew out of the country. 

Cooper earned his instrument rating and commercial license in 1982, then passed the test to become an instructor in 1984. After moving to the Cape Region in 2004, he taught classes with Garrett Dernoga in Georgetown. Unfortunately, the recession forced closure of the flight school. Although he doesn’t teach regularly anymore, he’s been working with his 13-year-old grandson who’s shown interest in flying. 

After retiring from the police force, Cooper worked for Brandywine Companies. One day while flying his employer to Tangier Island for lunch, the boss asked Cooper if the company needed an airplane.

“You never ask a pilot that question,” he said, laughing. 

Cooper found an Aztec in Kansas City, and his boss bought it, so he went out and flew it back. He flew for Brandywine every few weeks for about five years. 

After relocating to Delaware, he flew for Melvin Joseph for about two years.

“I was right seat; I never was captain on it,” he said. “That was a jet. We went to places like Las Vegas and New Orleans.” 

While it was fun to fly a jet, he said, smaller planes are more fun in their own way. 

Cooper has owned about 10 different planes. The most fun to fly was a Fuji, a Japanese plane. 

“Janet and I would take it to air shows on military bases and set up for the whole show, the entire weekend,” he said. 

A highlight was when he was invited to fly in formation with other planes around the Wright Brothers Memorial in Kitty Hawk, N.C., as part of the 111th anniversary of the brothers’ first flight. 

Another was two years ago when he flew cross country from Sandpoint, Idaho, with his son Rob. 

“It took three days and 21 hours of flying,” he said. “We flew through the Rocky Mountains, around Mount Rushmore and [over] the Field of Dreams in Iowa. It was cool to see a few things on the way back.” 

Nowadays, Cooper flies for fun. He’ll take his family on flights, or offer to take along someone interested in seeing the area from a different perspective. A few days after the award ceremony, he took his grandson to Cape May, N.J., for breakfast. 

His wife has been his co-pilot, so to speak, the entire 50-year span. Although she said she wouldn’t fly to the Bahamas today, she cherishes all the experiences she and her husband have shared over the years. 

“There were just a lot of enjoyable things I wouldn’t have done if I wasn’t married to a pilot, and I’m very thankful for that,” she said. 


  • TThe Cape Gazette staff has been featuring Saltwater Portraits for more than 20 years. Reporters prepare written and photographic portraits of a wide variety of characters in Delaware's Cape Region. Saltwater Portraits typically appear in the Cape Gazette's Tuesday print edition in the Cape Life section and online at To recommend someone for a Saltwater Portrait feature, email

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