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From the Jumpseat: Meet MDW First Officer Emanuel Prince

From the Jumpseat: Meet MDW First Officer Emanuel Prince

March 17, 2025

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Going through upgrade training, new Captains are taught the importance of setting the tone on the flight deck. Getting to know First Officers is my favorite aspect of sitting in the left seat. I’ve learned there are many unique paths people have taken to occupy a seat on a Southwest Airlines flight deck. But what amazes me even more is that over the course of my career, I will only get to know a fraction of our 11,000 Pilots.

I hope this column helps remedy that. From the newest First Officer taking flight to the most senior Captain knocking on the door of retirement, our ranks are filled with Pilots of every walk of life. And every one of them has a story to tell. Last month, we sat down with Kirby Chambliss and learned about the path that led him to becoming a Southwest Airlines Pilot and aerobatic and air race champion. This month, I’d like to introduce you to MDW First Officer Emanuel Prince.

Prince is a professional aviator, and his path into the right seat had challenges and detours. He grew up in a two-bedroom apartment on Chicago’s West Side. His mother and stepfather battled addiction and left Prince and his eight siblings to find their own way. Prince spent his time playing football and basketball during a time when the Chicago Bulls were everything and most kids wanted to “be like Mike.”

“I just wanted to be a Pilot,” Prince remarked. “While most kids were watching basketball on TV, I was watching jets flying in and out of O’Hare.” When Prince turned 13, he left the cramped apartment and moved in with his biological father. But his hope for a stable home life was cut short when his father went to prison for robbing a bank.

Prince didn’t let that derail his dreams. He is quick to point out that this led to his interaction with a handful of people who changed the trajectory of his life. After a short stint living with his aunt in Kentucky, Prince returned to Chicago to live with his mother’s father — a steel plant worker and disciplinarian who demonstrated the importance of hard work. “He taught me to ‘be well,’” Prince recalled. “Well dressed, well mannered, and well spoken.”

And he is. Over the course of our conversation, Prince told me how his grandfather paid for him to travel to Washington, D.C. with his eighth-grade class — his first time ever on an airplane — and solidified his dream of becoming a Pilot. “The only problem,” Prince said, “was that I had never met a Pilot who looked like me.”

“But it wasn’t a Pilot who looked like me who encouraged me to follow my dreams,” Prince said. “He wasn’t even a Pilot.” While attending a predominantly Black high school, Prince met an Italian American by the name of Jerry Calabrese, a McDonald’s corporate Vice President, who was so impressed by the well-spoken and well-dressed young man that he offered Prince a summer internship. When Prince confessed to Jerry that he didn’t think it was possible to realize his dream of becoming a Pilot, Calabrese offered him an internship with the McDonald’s corporate flight department.

Following graduation from Daniel Webster College in Nashua, New Hampshire, where Prince earned his Private Pilot’s License, he continued building flight time while working on the ramp in Miami and Boston. His interaction with Southwest Airlines employees led to him applying for a ramp agent supervisor position in Baltimore, a position he started on January 23, 2014.

While working in Ground Operations, Prince spent time in Atlanta and Detroit, before returning home to Chicago to serve as the assistant station manager. Each step along the way, he continued balancing his obligations at Southwest Airlines while working toward his ratings. “I had the money, but I didn’t have the time,” Prince recalled, commenting that he often showed up to work as MDW assistant station manager at 0430 and worked until 1500, when he would leave to instruct student Pilots at Bollingbrook (K1C5) until 2000. He burned the candle at both ends until January 2022, when he resigned from Southwest Airlines to pursue flying full time.

Over the next two years, Prince flew cargo in the Short 360 for Air Cargo Carriers out of Milwaukee and Puerto Rico; right seat in a CJ3 to carry Jeremy Biddle (a.k.a. “Yung Bleu”) and other music artists on tour; charters in the PC-12 and King Air 200 for Ward Aviation in Grand Rapids, Michigan; and finally, as a NetJets Pilot in the Citation Latitude.

On January 23, 2024, exactly 10 years after he started working for Southwest Airlines as a ramp agent supervisor, Prince started new hire training as a First Officer. He’s finally where he wants to be, but his mission is far from over.

Prince volunteers as a mentor with the Tuskegee NEXT Foundation; serves as the President of the AIMSIR Group (founded by fellow SWAPA Pilot, Sean Smith), providing guidance and financial assistance for those aspiring to become professional Pilots; and travels the country on his own time (and dime) to inspire kids across the country.

Prince laughed with unassuming pride when told me about one of his mentee success stories, an Italian American working his way through his ratings. “He doesn’t look like me, but it feels like my life has come full circle. It’s fitting that an Italian American gave a Black kid from Chicago’s West Side his start in aviation, and now that Black Pilot is mentoring an Italian American and giving him the same shot. I know that makes Jerry proud.”

 

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