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South Side Harbor Mainstay, 80, Has Lived on His Boat for 30 Years

By Seth Schwartz | August 7, 2015 5:47am | Updated on August 10, 2015 8:22am
 Al Thompson has lived in Jackson Park Harbor since 1984.
Al Thompson
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JACKSON PARK HARBOR — For the past three decades, Al Thompson has called the calm waters surrounding Jackson Park Yacht Club home. Literally.

From May until late October every year since 1984, the 80-year-old retired Chicago Public Schools teacher has lived aboard his sailboat — now a 30-foot Hunter with a 200-square-foot cabin. He pays about $2,200 per season in fees.

Well-seasoned in sail, motor or virtually any craft on the water, he is still sought for lessons and advice on sailing. He also keeps a watchful eye on the harbor — and is happy to share about his adventures sailing around the world or about his record-setting college basketball days in Mississippi.

“Teaching comes naturally for Al,” said David Ward, a Jackson Park Yacht Club member for 20 years. “Al’s personality is a good fit for Jackson Park. People are friendly and are willing to share their knowledge. If there’s a question on a boat, Al usually has the answer.”

“Al is always looking out for everyone’s best interest and the boats' best interest,” said Bryan Finigan, who's lived in the harbor for three years. “He’ll check and make sure everything is tied down on the docks. ... He’s given me a lot of assistance sailing my boat. It’s a steep learning curve and he’s been very instrumental in helping me succeed. He’s very perceptive and pays attention to the world around him."

The Jackson Park Yacht Club was founded in 1896, three years after the World's Fair.

Several times every summer, Thompson takes groups on trips north to Downtown or to 31st Street Beach. For shorter excursions, he still goes out on a modified 1972 Butterfly which fits his free spirit.

“I use a PVC pipe to reduce the mast area, the sail is from an iceboat and I use an aluminum boom,” said Thompson, who also travels occasionally on a jet ski. “I took the rudder and tiller from the Sunfish and put a cushion from a powerboat which makes it comfortable. When I tack, I don’t have to move.” 

Lunch is his only meal, which he eats daily at La Rabida Children’s Hospital, which is located across the street from Jackson Park Harbor.

An electric mattress pad and space heater keep him warm on cold evenings in the spring and fall.


Inside Al Thompson's 200-square-foot home. [Gary Bybee]

Fully Unplugged

With no cell phone, television or computer, Thompson spends most of the day chatting with the long-time regular members of the club. Occasionally he’ll stop into the Jackson Park Yacht Club to watch a movie before retiring around midnight. Up by sunrise, Thompson finds time to keep up with writing in his journal or ride into town or go home to do errands.

“Sometimes I’ll get up at 5:30 a.m., walk to the other side of the hospital and watch the sun rise off the water,” he said. “Watching the sun set from the boat is real nice. We still have a group of 10 people from the 1980s so there’s plenty of company.

“I see the cars lined up [on Lake Shore Drive] and I am glad I haven’t had to fight the traffic to get to work for over 20 years,” he said. “I have speakers wired up to listen to music and I have an awning to keep me covered during storms.”

During the winter, Thompson lives on the first floor of a two-flat at 73rd Street and Luella, in South Shore, where he’s been since 1968.

Twice married, he has a daughter, Koli, who lives across the street in South Shore, as well two sons, Jason and Guy. Thompson grew up in East New York, Brooklyn, the son of a mother from Virginia and Haitian father. Thompson’s father was a furrier who passed away when he Thompson was five. A piano teacher, his mother raised him and two older brothers who became professional jazz musicians.

In the 1950s, Thompson went to Tougaloo College in Mississippi where he played basketball and graduated with a degree in physical education and biology. His 62 points on the road and 49 at home are still school records.

He moved to Chicago, and for two years he drove a Chicago Transit Authority bus.

He then went to work for Chicago Public Schools, where he worked as a physical education teacher at DuSable High School from 1960 to 1979 and at Williams Elementary from 1979 to 1990. Among his students were Maurice Cheeks, who went on to a 15-year career in the National Basketball Association.


[Gary Bybee]

Summers of Sailing

With summers off, Thompson bought a 15-foot catamaran sailboat in the late 1960s. After a dozen-plus capsizes in Lake Michigan, Thompson became a natural, sailing out of South Shore and 79th Street beaches.

By 1984, Thompson was ready for greater adventures and bought a 25-foot Hunter for $6,000. At about the same time, he met Bill Pinkney in a ski club and the two became friends and travel partners.

“Bill was a mentor for me,” said Thompson. “I learned a lot about navigation and we always had a good time. Bill was docked at Belmont Harbor, so I’d usually sail up and then we’d go from there. He’d take his boat and I’d go in mine.”

So-called "beer can races" on Wednesday nights is where Thompson started making his name as a speedy sailor.  

“You really learn the four points of sailing,” he said. “We had about 30 boats that were around 25 feet, so it was always competitive.”

In 1990, he and his girlfriend and two friends on another boat spent 38 days sailing around the western part of Michigan and down the Wisconsin shoreline.

“We’d start going to Michigan City, St. Joseph, [Mich.], and worked our way up coast,” said Thompson. “We’d go about 30 miles a day and then anchor in a marina at night. We brought fold-up bikes and at each harbor there’s always a lot of fun.”

'The 1st Black Sailors We've Seen'

Pulling into Pentwater, Mich., one day, they surprised the locals.

“They said, ‘You’re the first black sailors we’ve seen here!’” Thompson said. “They couldn’t have been nicer. We stayed three nights and were given royal-carpet treatment.”

In 1994, Thompson flew to Europe and then to Egypt. Taking a water taxi on the Nile, he inquired about skippering. Thompson got the boat going at maximum speed up the river and had it heeling during the four-mile trip before maneuvering it to the dock. The owner was so impressed he invited him into his home to smoke his water pipe.

Thompson’s excursions weren’t confined to the water. An accomplished skier for over 40 years, Thompson and friends have been skiing at various locations out west where they would meet up with members in one of three black ski clubs.

Other trips during the 1980s took him to Austria, Switzerland and Italy. The principal at Williams Elementary insisted Thompson bring his skiing trophies from summits to school to show the children and share details on his victories.

The stories are familiar to Thompson's harbor-mates.

“I guess you could say Al is well traveled and ages well,” said Finigan.

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