NHS Alum Spends 25 Years in the Air Force, Now Teaches Students to Take Flight

Writer  /  Christy Heitger-Ewing
Photography Provided

After graduating from Noblesville High School in 1986, Skip Bailey went to Indiana University where he struggled to determine what he wanted to do with his future. His dad, who had gone through the ROTC program, encouraged his son to do the same.

“I wasn’t crazy about the military, but I gave it a try,” says Bailey, who took the AFOQT (Air Force Officer Qualifying Test) and scored exceptionally well on the aviation and navigation sections. After seeing the results, the Colonel asked Bailey if he could send him to pilot training and teach him to fly. Wide-eyed and intrigued, Bailey was sold.

After finishing college, he got his commission as second lieutenant in the Air Force, then went to pilot training at Williams Air Force Base in Mesa, Arizona.

In December 1991, he married Sherry, whom he had met at IU. At the time he completed pilot training, the Air Force had too many pilots and not enough airplanes so they sent two-thirds of his pilot training class to do something else. Bailey used the opportunity to earn a master’s degree in criminal justice from the University of South Carolina. After which, he returned to flying.

In 1994, he went to Offutt Air Force Base in Omaha, Nebraska, where he flew the EC-135 — a plane that was called the Looking Glass because its mission was to be airborne constantly in case of a nuclear strike by the Soviet Union. It flew three eight-hour flights a day.

“It could mirror what the United States ground missile launchers could do and launch nuclear missiles in a retaliatory strike from the air in case the ground bases were destroyed,” Bailey says. Considered a Cold War weapon, the plane has since been retired.

In 1998, Bailey and his wife moved to McGuire Air Force base in Trenton, New Jersey, where he flew the KC-10, an aerial refueling plane. As the name suggests, these are planes that refuel other aircraft while in the air. Bailey did this from 1998–2002 before going back to Offutt to fly the E-4B, a Boeing 747-200 model airplane modified for Air Force use. The primary mission of the E-4B is to be close to Air Force One and the president at all times in the event of a worst-case scenario.

“We’ve been called Air Force One Back-up and Air Force Two. We are a communications platform so the President can communicate with anybody around the world,” says Bailey, noting that this plane has a prominent role in the Tom Clancy thriller “The Sum of All Fears.”

“A small nuclear device goes off and they need to get the Vice President on board the E-4B to keep him safe,” Bailey says of the book.

The backup job of the E-4B is to take the secretary of defense and his staff anywhere they need to go. So while Bailey has never been on Air Force One, he’s flown five different secretaries of defense to various parts of the world.

“It was a fantastic job,” Bailey says. “My fun fact, whenever I’m at a party, is to share that I’ve been to every continent in the world except Antarctica.”

After five years, Bailey took a job as an ROTC commander at Ohio’s Kent State University.

“That kind of brought me full circle,” says Bailey, who remained in that position until 2010. He then flew the E-4B again from 2010–2016.

After retiring from the Air Force in 2016, he landed a job as flight training coordinator at the University of Nebraska at Omaha in its aviation department. He teaches ground school classes for aviation and is also in charge of overseeing the flying of all of their professional flight students — this semester that’s 99 students.

It was an adjustment to go from military aviation to general aviation as getting acquainted with the FAA regulations took some time.

“It’s a steep learning curve figuring out all of the differences,” Bailey says. “Going from military to university is a complete 180.”

Teaching students the basics of flying — e.g., what lift means, what drag means, what winds will do to an aircraft — is enjoyable for Bailey. He also enjoys watching his students progress through the program and graduate.

“To know that I had a piece in their success is very satisfying,” he says.

Bailey and his wife have three children: Nick (21), a junior at the University of Northern Colorado, Beth (21), a junior at Truman State University in northeast Missouri, and Tori (17), a high school junior who is committed to playing soccer at Emporia State University in Kansas. They also have two Boston terriers — Ginger and Gus. Skip and Sherry have enjoyed building a life in Nebraska.

“My wife and I always joke that if you take Indianapolis, cut it in half, size-wise, and move it 600 miles west, you have Omaha,” Bailey says. “It’s the same climate, same people. There’s a lot of corn everywhere. It feels like home.”

When Bailey was in the Air Force, he traveled extensively. He’s been to 38 countries around the world and looks forward to returning to some of those places with Sherry. For their 25th wedding anniversary, the pair toured Italy.

“We’re big wine fans so that was a logical spot,” Bailey says. When all three children graduate from college, the family plans to take a European vacation. Also on Bailey’s bucket list: exploring Tokyo and Paris with Sherry. But he’s not rushing life as he’s content just where he is.

“It amazes me when I think about my 25 years in the Air Force,” Bailey says. “Being a small-town Noblesville boy who had a hard time thinking ahead to the next weekend, let alone envisioning a career, I never would have imagined the path I’d take. I give credit to my parents for getting me there.”

At the same time, he’s learned the futility of making plans.

“Whenever my wife and I have made plans, God laughs,” Bailey says. “But it has all worked out the way it was supposed to. I feel very lucky.”

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