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Chicago’s oldest-known sailor keeps the wind at his back

Longtime sailor Ed Stein, 99, plans to be back on his boat, Dog House IV, on Memorial Day. | Mitch Dudek/Sun-Times

At 99, Ed Stein, is still impatient about getting his boat in Lake Michigan.

Restless water-watching from his lakeside condo ends this weekend when the sailboat of Chicago’s oldest mariner slips back into the water.

One of the first things to do: attend the Memorial Day flag-raising ceremony at Chicago Yacht Club, something he’s been doing for decades.

Stein started sailing in his teens, so he already had plenty of experience on the water when World War II started. And Stein did serve in the Navy — eventually.

“I tried to join when things first broke out, but because of my eyes they wouldn’t let me in,” said Stein, who is nearsighted.

“I guess they thought I might find the wrong people to shoot,” Stein joked this week during a lakeside chat over coffee.

“But finally the government got down to the bottom of the barrel and I was drafted,” he said. “And the day I was drafted they said ‘Do you want Army or Navy?’ And I said ‘Are you kidding? Certainly I want the Navy!'”

Stein, who grew up in Beverly, was sent to train at a base in the Finger Lakes region of upstate New York. When word of his extensive sailing history in Chicago filtered up to officers, they put him in charge of maintaining a small fleet of new sailboats.

“The boats were brought in under the R&R (rest and relaxation) program, and the officers from the hospital and the base used to race them on the weekends,” said Stein.

Because his family ran an attache-case manufacturing business in Chicago, Stein knew how to sew the sails.

“And of course, in the meantime, I’m living in the boathouse and all these guys that had sea duty were wondering what kind of crap I’m doing fooling around with sailboats when we’re fighting a war. And I said ‘Well, I’m just following orders.'”

He bought his first sailboat out of the back of a magazine. It arrived at his home in a box — assembly required. So he put it together in the basement, though getting it out of the basement once it was completed was a little hairy.

A few years later, in 1936, he bought a boat that someone else had put together. By then, he was dating the woman who would become his wife (that’s Millie, now 97). So he named the boat the Dog House, a tongue-in-cheek reference to where he resided as a result of sailing so often. Each boat he’s owned since has had the same name. He’s on Dog House IV.

“He’s certainly the oldest active sailor that we know of,” said Scott Stevenson, who runs Chicago’s harbor system.

“I don’t think there’s anyone within 10 years of him on the water,” Stevenson added. “I hope to have half of his energy and ability when I’m that age.”

Stein, a decades-long member of the Chicago Yacht Club, also served several stints as commodore of Columbia Yacht Club. He headed up Chicago Sea Scouts — a Boy Scouts program that teaches kids how to sail — and in 1970 dressed up as Neptune, God of the Sea, to march with Mayor Richard J. Daley in the Venetian Parade.

His marching these days mostly consists of treks up and down the long hallway outside his front door to maintain the strength and stamina required to get out on the water.

“You know the old saying, ‘If you don’t use it, you lose it,'” said Stein.

“There’s eight people on my crew. . . . I sit aft, next to the wheel. I still steer some,” said Stein, who plans to sail every weekend this summer. His lake excursions are relaxed. A cooler of beer is usually present, though Stein doesn’t partake.

“He tells me all the time not to worry about him and I try not to,” said Myrna Stein, one of Stein’s two daughters. “If it’s his time, it’s his time. He’s doing what he wants to do.”

Will he ever give it up?

“Never. Never. Never.”

At 99, Ed Stein is believed to be the oldest active sailor in Chicago. He plans to be out on Lake Michigan again this Memorial Day. | Mitch Dudek/Sun-Times
At 99, Ed Stein is believed to be the oldest active sailor in Chicago. He plans to be out on Lake Michigan again this Memorial Day. | Mitch Dudek/Sun-Times