Just three days before he’d planned to visit Jackson Park Harbor one final time, Jack Lyle, one of the legendary Tuskegee Airmen, died Saturday at his South Side home.

Even though he was going to have to get there via ambulance and stretcher, he was determined to see Lake Michigan because he loved to sail as much as he loved to fly.

Mr. Lyle, who had prostate cancer, was 98, according to his wife Eunice. His remains were cremated and she hopes to scatter some of the ashes in the lake he loved.

Tuskegee Airman Jack Lyle named his plane Natalie for his first wife. | Facebook photo

He’d intended to enjoy the harbor Tuesday from his favorite shaded bench, said Janet Hansen, commodore of the Jackson Park Yacht Club. “He wanted to sit on his bench one last time and go and view the lake from the point.”

Hospice workers “asked Jack what would be his one wish before he passed, and he said he wanted to go to Jackson Harbor and look at the lake,” his wife said.

In 2007, President George W. Bush and Congress bestowed the Congressional Gold Medal on Mr. Lyle and the other Tuskegee Airmen. The members of the nation’s first black fighter squadron won acclaim for their aerial prowess and bravery, despite a military that segregated them, and southern “Whites Only” entrances that permitted German prisoners of war–but blocked African-Americans. Mr. Lyle, who named his plane “Natalie” for his first wife, once shot down a German Messerschmitt, according to an honorary resolution by the Chicago City Council.

“We flew 500 feet above the bombers to keep enemy fighters from hitting our guys,” he recalled in a 2012 interview with Jet magazine. . “. . . . I loved flying, being up in the clouds, the scenery. I flew 26 combat missions, from southern Italy to Austria and southern Germany, over the Austrian Alps.”

“I was shot at several times as part of a formation. I watched bombers being torn apart, but they were performing the mission they signed up to do,” Mr. Lyle told Jet. “And when I had to shoot the guy who was shooting at the planes I was protecting, I did not feel bad because that was my assignment.”

Jack Lyle and other Tuskegee Airmen were awarded the Congressional Gold Medal in 2007 for their World War II service. | Facebook photo

“He had no fear,” his wife said. “None at all.”

A graduate of Englewood High School, he was engaged and inspired by his mother, the singer Ernestine Lyle, who performed in a quartet and with the American Negro Light Opera Association. She enrolled him in piano and violin lessons, according to his wife.

“His mom bought him a 50-volume set of the Harvard Classics,” she said. “He was very well-read.”

After the war, he served as a police officer with the Chicago Park District and founded a tree-trimming company. “I was in the tree business for 30 years because I liked being out in the open — having the time to think,” he said in the Jet interview. “Later, I took up sailing because it was the same idea of being free and on your own.”

Jack Lyle taught many other sailors how to navigate at Jackson Park Harbor. | Provided photo

“He was an amazing sailor,” Hansen said. “He could sail his boat in any weather.”

Mr. Lyle piloted a sailboat his wife christened the “Night Watch.” He guided other Jackson Park mariners on what to do in emergencies, like loss of power. “He taught a lot of people how to sail so the wind was always their motor,” Hansen said. “You have to understand the wind to be a pilot, whether it’s in the air or a sailboat.”

The Auburn Gresham resident drove a Chevy truck and rode a motorcycle. And he enjoyed books on sailing and by the philosopher Noam Chomsky.

Mr. Lyle also dabbled in inventions, including the “Exerball,” an exercise ball rigged to the waist.

“Some of them were hilarious, like loincloths for men,” his wife said. They named the prototype the “Jonfre.” He also created leopard-print men’s underwear he called “Tuckems.”

Mr. Lyle excelled at chess, trained in jiu-jitsu and was an expert marksman, she said. “He was my hero. . . . He taught me how to protect myself with martial arts, how to shoot a bow and arrow, how to shoot a gun.”

“It was a ride with him, a wild ride,” said Eunice, his fourth wife. She used to say, “I’m No. 4, there’ll be no more.” Married 37 years, they met when his tree-trimming equipment broke one of her lanterns. She insisted he pay for it.

Her children Cynthia Kincey, Kathy Holliday and John Jackson also survive him.

In 2017, Argus Brewery in Pullman rolled out a beer in his honor, “Tuskegee Airmen Pursuit.”

“He was a personal hero,” said Chad King, a U.S. Army veteran and member of the Jackson Park Yacht Club. “I just miss the fact I wasn’t able to give him a final hand salute. That was my intention Tuesday.”

“The airmen made a contribution to our country,” Mr. Lyle told Jet. “And even though there was a lot of racism then, a lot of other people think so, too. Once, I went to a bar in full uniform and some white guys started approaching me. I was watching them. Then, they broke into smiles and started thanking me, saying, ‘You’re one of those people that protected our guys.’ “

Jack Lyle sailing on Lake Michigan. | Leslie Travis photo