Pilots: Dennis Flanagan

When you board an airliner for that sardine-packed journey through the skies, someone in a uniform usually stands at the door and smiles mutely. Unless it’s Dennis Flanagan. A United Airlines captain, Flanagan has become a legend among travelers. He writes each first-class passenger a personal note on his business card. He snaps photos of pets inside the cargo bay to show owners the pet is OK. He takes kids traveling alone into the cockpit and explains how the airplane works. He takes their picture in the pilot seat and sends it to their parents and calls them to tell them how their child is doing, where they’re seated, and if the flight’s going to arrive late. When a soldier is flying with Flanagan, before boarding he’ll announce over the intercom that the soldier is on the flight and ask if any first-class passengers would care to exchange seats. “The response is always 100 percent,” Flanagan says.

Which begs the question, “Why?”

“You deserve a good travel experience,” says Flanagan, 56. “When I crawl into a car with you I expect a safe ride. I give people what I expect to get.”

Flanagan began flying in 1971 while attending Kent State University, earning his private and instrument credentials in a Cessna 150 and 172. In 1974 he joined the U.S. Navy and flew transports: King Airs and ski-equipped C-130s in Antarctica as part of Operation Deep Freeze. He finished up his 20 years of service in the reserves, flying P-3 Orions, and soon after joined United as a flight engineer. In the third seat he began watching the captain. “The captain sets the tone when you fly,” he says. It didn’t take long for him to decide what kind of captain he wanted to be. The kind who lets the passengers know what’s going on. The kind who’s, well, kind.

The cockpit visits can have a lasting effect on the kids. “I was a 727 flight engineer in 1988. A mother took a picture of a child in the cockpit with me and mailed it to me,” he says. “She sent another to me 18 years later when he had his pilot certificate.”

Today Flanagan flies mostly domestic routes; you can’t meet as many people on international routes, he says.

It’s not all about making the customer happy. Take the last day of last year, when he was ground-delayed in San Diego en route to Chicago. He opened the cockpit for passengers to check out. “A parent took my photo with her normal, average-looking son,” he says. “Upon deplaning in Chicago she handed me a note thanking me for the photo opportunity. Her ill son was at Legoland on his Make-A-Wish flight. I didn’t even know, but it made my heart smile.”