The Accidental Presidential Guardian
Arthur Raymond Jackson Jr. never intended to spend his career protecting presidents. When the 19-year-old walked into a Washington D.C. recruiting station in 1993, he had no idea his recruiter was setting him up for a lifetime of missions he couldn’t have imagined.
“My recruiter, who actually happened to be an African American fighter pilot, was like, ‘Hey, you qualified,'” Jackson recalls from his Hawaii home, where he still supports the same aircraft he once supervised. “And I was like, ‘That’s great. What does that mean?’ I had no idea what he was talking about.”
The job description said, “airborne computers.” Jackson figured he’d be jumping out of planes with laptops. Twenty-four years later, Master Sergeant Jackson would retire as one of the most experienced presidential aircraft crew members in Air Force history, having ensured the safety of everyone from Bill Clinton to Michelle Obama across the Pacific theater. “I did work on airplanes. I did work on computers,” Jackson laughs. “I wasn’t jumping out of them.”
Jackson discovered early that his career would be defined by CNN headlines. “Every time there was breaking news on CNN, I was packing my bags and getting ready to go,” he says. “We were always in the middle of things.” His deployments stretched from Kosovo in 1999 through Afghanistan in 2013-2014, working as an Airborne Warning and Control Systems specialist on those massive radar planes with distinctive rotating domes.
But Jackson’s transition to presidential aircraft duty happened by accident. He was in Seattle working with Boeing when his time was up, and Hawaii had the only available slot on his dream sheet. “I wasn’t necessarily selected for it. I just kind of ran into a situation that worked out for me,” he explains. As squadron superintendent in Hawaii, Jackson found himself responsible for the only VIP fleet serving executives, generals, admirals, and former presidents across the Pacific — a region stretching from Africa to Washington, D.C.
Flying the President He’d Voted For
The most memorable mission was flying President Clinton to Singapore. The flight held personal significance for Jackson, who had voted for Clinton in 1992 while at Howard University — his first time voting in a presidential election. “It was kind of surreal,” Jackson reflects. “I voted for Bill Clinton in 1992 at college, so it was surreal flying him to Singapore from Hawaii.”
Long flights gave Jackson insights into high-profile passengers that television viewers never see. Flying someone for 14 or 15 hours reveals a different person than the one who appears in carefully managed public appearances. “You get to see people in a different way when they’re flying on the plane for 14, 15 hours,” Jackson explains. “It’s different than just seeing them on TV. You get to hear that they have a different presentation on TV than they do one-on-one in person.”
Jackson wasn’t assigned to the Presidential Airlift Group in Washington D.C., but his Hawaii unit regularly supported presidential missions. The formal process for the most prestigious assignments requires assignment to the 89th Operations Group, which supplies support personnel for what they call the “top five” — the Chairman of the Joint Chiefs of Staff and all the secretaries of defense. “You have to go there, prove yourself, and then they allow you to get assigned to the PAG,” Jackson explains, referring to the Presidential Airlift Group.
Jackson had two troops from his Hawaii unit who successfully made this transition. One became an engineer, the other a flight attendant, both serving at the PAG. It’s a pipeline Jackson helped create through his leadership and training approach — something that would become crucial to his later philosophy about developing people.
The Service That Earned By-Name Requests
Jackson’s Hawaii unit developed something special: a reputation for personalized service that earned them “by-name requests” from high-ranking officials. “We are a smaller unit. We only had two airplanes,” Jackson explains, “but because we had a smaller unit, we took a little bit more care in how we delivered service to our customers.”
The requests came from the highest levels. Officials would specifically ask for Jackson’s Hawaii team to fly them to places like Poland, even though it meant the crew had to travel from Hawaii to D.C. first. The secret was personalization. Jackson’s team learned passengers’ favorite drinks and meals, discovered personal preferences, and celebrated birthdays mid-flight.
He recalls one regular passenger, Undersecretary of Defense Frank Kendall. Jackson’s team made Kendall’s favorite meals and learned what he liked for his birthday. “We went over and above to try to customize your travel experience,” Jackson explains. The reputation spread through word-of-mouth at the highest levels of government. Officials would tell their schedulers they wanted Jackson’s team specifically.
“If you do a good job, they’ll say, ‘I know I’m supposed to fly with those guys, but I want these guys to come take me,'” Jackson says. “And if they rank high enough, they can do that.” One mission that exemplified this approach was ensuring Michelle Obama could attend her 50th birthday party with Oprah after finishing her Hawaii vacation. “One of the highlights of my career,” Jackson says, “was making sure that Michelle Obama was able to get over to her 50th birthday party with Oprah.”
Creating the Oval Office in the Sky
Presidential aircraft operations don’t follow normal schedules. Jackson’s team worked until missions were complete, whether that meant starting at 1 a.m. or 1 p.m. “We don’t watch the clock because it really doesn’t matter,” Jackson explains. “We don’t get off at a certain time. It’s really until the mission is complete.”
Jackson describes his role as being like “a big-time travel coordinator,” worrying about hotels, transportation, visas, passports, costs, and host nation agreements. As a supervisor, he also ensured his people had emergency action plans for getting everyone to embassies if something went wrong in foreign countries.
Pre-flight preparations focused heavily on communications. Jackson’s team ensured every system worked perfectly before any principal boarded. “Think of the airplane as kind of an extension of the Oval Office in the sky,” Jackson explains. “Everything you would have in an office — telephones, video cameras, fax machines, emails, secure and nonsecure communications — we have the ability to do in the air.”
The technical complexity was staggering. Jackson’s team managed satellite communications, liaised with ground stations worldwide, and ensured that presidents were able to conduct official business without interruption while at 40,000 feet. His team coordinated globally, reaching back to D.C., connecting with local embassies, and communicating with various players who needed to know what was happening.
Jackson confirms what many suspect about presidential aircraft security but won’t elaborate on specifics. “You’re a bodyguard in the air. Yes, I won’t speak to what we carry, but we are prepared for that.” The security preparations extend far beyond what passengers ever see, with Jackson’s team coordinating with multiple agencies, maintaining secure communications, and preparing for contingencies that most people never consider.
When Everything Goes Wrong at 40,000 Feet
Emergency situations tested Jackson’s crew most severely. He recalls multiple incidents where split-second decisions and flawless teamwork prevented disasters — engine problems over Alaska, cracked windshields halfway across the Pacific, safety issues identified at the last minute while flying from Alaska past Russia to South Korea.
“There were moments where we would have an engine problem, and we had to come up with a solution. We can’t turn around,” Jackson recalls. “Cracked windshield over the Pacific Ocean, halfway between Asia and Hawaii, where the crew figured out a divert and came up with a plan for coming back to Hawaii, landing safely.”
These emergencies revealed the strength of Jackson’s team selection and training. Problems got solved because everyone backed each other up. “If you have a good crew, those problems get mitigated and you don’t really worry about something going to be missed,” Jackson explains. He can’t recall a single time his team missed something that created a real safety issue.
Jackson explains the Air Force’s approach to safety using a concept that applies far beyond aviation. “In the Air Force, we’re taught to pay attention to detail,” he says. “It’s not about how many push-ups you can do or how fast you can run. It really comes down to: can you pay attention to detail and do something very complex and do it right without being corrected?”
When you have 19 to 20 people on an airplane all paying attention to detail, Jackson explains, you get what’s called the Swiss cheese model — where holes in one person’s coverage get filled by others paying attention. “So, I’m very proud that we didn’t have any safety issues while I was flying,” Jackson says.
The Brutal Reality of Pacific Operations
Pacific operations demanded everything from Jackson’s crews. Missions stretched from Africa to Washington, D.C., sometimes requiring 23- to 24-hour duty days. “Sometimes you’re looking at 23, 24-hour days,” Jackson explains. “You’re doing constant flying and trying to stay hydrated, trying to stay conscious, trying to make sure everything is good and the communications are flowing.”
These “milk runs” happened two or three times monthly, wearing crews down physically and mentally. Smart leadership meant managing crew rest strategically. Jackson cycled people off duty except during critical phases like refueling stops or when meal service was required. His career field didn’t get extra personnel, so sometimes it was just Jackson and one other person trying to stay awake on flights to New Delhi.
The jet lag was brutal. Jackson learned this personally when traveling to Europe with his wife. “Rest is huge, and then when you get to your location, as my wife discovered when we went on a trip to Europe, it’s very hard to sleep when you’re on the opposite side of the world and your body clock is tuned to some other location. It gets to be a little bit of a challenge, I told her, hey, welcome to my world for 23 years.”
Jackson highlights something distinctive about Air Force operations that sets them apart from other military branches. “Let me take my hat off to the flight attendants because they work really hard,” he says. “When the plane is in the air, they are making sure all of the meals are made.” The Air Force approach was unique among military services. “We actually pick the person to be a flight attendant, then we teach them how to cook. Not the other way around. All the other services do it the other way around.”
This philosophy — selecting the right people first, then training them for excellence — would become central to Jackson’s leadership approach. The work ethic required was intense. Jackson’s people often worked from eight in the morning until ten at night, prepping for missions. “We make it look easy,” Jackson says, “but typically, guys would come in to work at eight, nine o’clock in the morning and they’d leave at 10 o’clock at night, prepping for a mission.”
He describes his people as “quiet professionals. They don’t say anything. They just go and do what they got to do, make sure everything is prepared. Make sure it’s on time, and then when it’s time to execute, they go about their business.”
Jackson takes pride in the complete service his team provided, ensuring safety and comfort while also delivering restaurant-quality meals served on chinaware. “We give you all the comfort, we make sure you’re safe,” Jackson says. “We’re also making sure that your meals are right. You get to choose what you want and then we give you quality food and make sure it’s served with china and the whole nine.”
Jackson’s leadership approach paid dividends beyond successful missions. Many of his former troops went on to prestigious assignments, including one who became Michelle Obama’s personal attendant after transferring from Hawaii to D.C. “I’m very proud of my time doing what we call VIP Special Air Missions,” Jackson reflects, “because a lot of my former troops went on to do other things and continue on in the world and do big things.”
But all of Jackson’s success in presidential aircraft operations — the by-name requests, the flawless missions, the crew development — came from something deeper than just following procedures. Early in his AWACS career, Jackson had learned a lesson that would transform not only his own leadership style but the effectiveness of every unit he touched. It started with senior NCOs who were very upset with him, and it would eventually earn him four Air Medals, multiple Achievement Medals, and the respect of everyone from undersecretaries of defense to former presidents.
In Part 2: The three-word philosophy that changed everything, the 80% veteran statistic that should concern every American, and Jackson’s direct message to today’s veterans struggling with transition.
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