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Black pioneer pilot retires, flies Southwest plane home one last time

Southwest Airlines Chief Captain Louis Freeman (left) flies in his final flight to Midway before retiring Thursday. He and First Officer Michael Frietag landed the plane to huge cheers from passengers before disembarking to more cheering. | Maudlyne Ihejirika/Sun-Times

Thursday was Capt. Louis Freeman Day in Chicago.

Freeman learned that with the rest of us after disembarking from the 737 plane he had flown in to Midway Airport from Dallas at 3 p.m., to hordes awaiting the arrival of Flight 4122.

That was this pioneering black pilot’s very last flight.

The Chicago area man retired Thursday, leaving behind a legacy of firsts: first black chief pilot to serve at any U.S. airline, first black pilot at Southwest, his home of 36 years. Going back a bit further, first black ROTC cadet corps commander in high school.

But his most lasting legacy — if you let the dozens of Southwest employees and customers, family and friends, who turned out for his send-off Thursday tell it — is that he cared.

“When I was 6 years old, I was flying back from Austin to Phoenix, and Mr. Freeman ended up sitting next to me,” recounted Brody Burnell, 18, of Phoenix, the son of a Southwest flight attendant who had cut short a vacation in Italy to be there.

Capt. Freeman listens as Brody Burnell, 18, of Phoenix, Arizona, talks about how Freeman influenced him to become a pilot when he was 6 years old. | Maudlyne Ihejirika/Sun-Times

“My Mom’s like, ‘I don’t want you to bother this man. He’s very important in this company.’ But I ended up talking to him about airplanes, and told him I really wanted to be a Southwest Airlines pilot when I grow up,” Burnell said. “He invited me down to a little party for recruiters. And I got a letter in the mail the next week, saying, ‘You’re in the pilot mentor program.’ I found out later that’s not really a thing.”

Freeman also sent him posters. Burnell graduated from high school last week with his commercial pilot’s license, and he is headed toward his goal. “He really influenced me,” Burnell said.

Freeman, now at the mandatory pilot retirement age of 65, was born in Austin, Texas, to middle-class parents. At age 10, his family moved to Dallas during the height of the civil rights movement. A year into high school, Dallas integrated its schools, and as a sophomore in 1967, he was sent to Woodrow Wilson High School, where he was one of only about a dozen black students out of 1900.

But he excelled in band and in ROTC, so much so that his ROTC leader fought to make him commander, against overriding faculty sentiment that cadets wouldn’t follow a black student. “Not only did they follow, our unit excelled,” Freeman recounts.

He attended East Texas State University, now Texas A&M-Commerce, joined the Air Force ROTC unit there and took the Air Force exam. He passed all but the pilot portion, having never been exposed to aviation. So he began studying aviation on his own.

“During that year, I fell in love with the idea of flying airplanes,” Freeman said.

Passing the exam the following year, he accepted an ROTC scholarship to the Air Force Academy, then in the late 70s was stationed at Mather AFB in California, where he met future wife Stephanie Woodfork, to whom he’s been married for 34 years.

“Lou was a pilot in the Air Force. I was a radiologist. We dated for five years,” said Woodfork, who is retired, and was awaiting her husband at Midway with their son Steven, who had flown in from Florida, and daughter Nikki, in from Seattle.

Southwest Airlines Chief Capt. Louis Freeman with his family, after flying his last flight in to Midway before retiring. His daughter Nikki (left), wife Stephanie Woodfork, and son Steven joined him. | Maudlyne Ihejirika/Sun-Times

“I remember when he was hired for Southwest in 1980, I waved goodbye to him, and he drove off in this car, a 240Z. I said, ‘Well, that’s the last time I’ll see him.’ Because he was going to Texas,” Woodfork said. “But we stayed together. Whenever he was off, he’d fly to California. I was in L.A. at the time, doing my residency. We married July 24th, 1982.”

Freeman began his career at Southwest on Nov. 10, 1980.

“Lou was the first African-American pilot hired by Southwest, and then later became the first African-American chief pilot of any airline at the time. He’s just a really inspiring person,” said Patty Greene, Southwest’s manager of community affairs, who was hired three months before Freeman and has worked with him for a few decades.

“Lou is such a mentor, someone that everyone looks up to. He’s very down to earth, very genuine, really wants to help others,” she said. “He’s friendly. He’s kind. He’s one of the first adopted pilots in our adopt-a-pilot program, where pilots work with fifth- and sixth-grade students, teaching them about geography, aviation, principles of flight, just a great man.”

“Lou was the first African-American pilot hired by Southwest, and then later became the first African-American chief pilot of any airline at the time. He’s just a really inspiring person,” said Patty Greene, Southwest’s manager of community affairs, who was hired three months before Freeman and has worked with him for a few decades. | Maudlyne Ihejirika/Sun-Times

Less than three years after being hired, Freeman became Southwest’s first black captain.

In 1989, he became its Phoenix Base Assistant Chief Pilot, and in August 1992, chief pilot at Southwest’s newest crew base in his hometown.

“It was an industry first. No other major airline had ever promoted a black pilot to chief pilot position,” Freeman recounts. “In my 15 years as Chicago’s chief pilot, it grew to be Southwest’s largest crew base, and I met three United States presidents, two presidential candidates, and a number of Cabinet members, including three secretaries of state.”

Along the way, there have been poignant moments: Freeman selected and led the three-pilot crew that flew the body of the late civil rights icon Rosa Parks on her final tour in October 2005: Detroit to Montgomery, Alabama, to Washington, D.C., and back to her final resting place in Detroit.

“When we flew into Montgomery, Alabama, a place that once used high-pressure fire hoses to block African Americans from peaceful protests during the Civil Rights Movement, we were greeted with a water cannon salute to honor Rosa Parks,” Freeman recounts. “We even wiggled our wings as Ms. Parks’ final goodbye as we departed Montgomery. The reception she received in Montgomery and Washington, D.C., was heartwarming, and having my family accompany me was priceless.”

John Addison, a Southwest pilot for 13 years, captain for three, flew in from Las Vegas.

“Pilot stuff aside, Lou is just the greatest guy. He’s nice to everybody. Even as a boss, he would come in here on Sundays and let everybody else have the day off,” Addison said.

“I bought my ticket today, because the flights are full. I couldn’t miss this, to honor Lou his last flight. The man is a leader. He’s an American hero,” he added. “Lou mentored me, helped me get from a regional airline to Southwest and the big-time. It’s because of the Tuskegee Airmen that Lou could do what he did. And it’s because of Lou that I’m able to do what I do. I hope to pave the way for someone else.”

John Addison, a Southwest pilot for 13 years and captain for three years, and flight attendant Caroline Brody, celebrate the retirement of Chief Pilot Louis Freeman of Southwest Airlines at Midway Airport on Thursday, June 8, 2017. | Brian Jackson/For the Sun-Times

Freeman, who actively volunteers for the Tuskegee Airmen’s group, was greeted with his own water canon salute by the Chicago Fire Department as his plane pulled in. And he exited the jetway to a high decibel of cheers, walking a gauntlet of high fives.

“It’s a bittersweet day,” noted his teary wife. “I retired before he did, a long time ago. He kept flying. He loves to fly. He loves Southwest. He loves Midway. He loves every employee of Southwest. I don’t care what department you work in. Louis loves them.”

And Freeman, after accepting his proclamation, said about the same.

“I enjoyed my trip from Dallas to Chicago. I wanted to savor every moment,” he said, audibly choking up. “I cannot believe the outpouring and love that I see and feel here. And when I realized airline employees who are used to asking airline discounts were buying tickets to come on the flight with me, that floored me, because that just doesn’t happen.

“I always have thought myself to be just Lou. Just Lou. Simply that. But I found out in the last month or two months or so, that maybe I’ve been a little bit more than just Lou, that maybe I’ve been able to touch you and you and you. And that makes me happy,” he said. “Because I know that if I’ve been able to reach out and touch and be good to somebody else, that’s my legacy. I want that to be the thing that people will remember about me. You will never know how much you’ve meant.”