Chicago’s Very Own: Don and Jennifer Wilson

Don and Jennifer Wilson were born to sail. It started when the siblings were kids, during the summers in Maine at their grandma`s house.

“It’s just something that I’ve always been really interested in from growing up,” Jennifer said.

“Well actually in high school I sailed. We lived in Switzerland and I raced 420 and then I raced in college,” Don said.

In 2005 Don discovered match racing — you’ve seen it at the America’s Cup.  Teams of sailors, competing in a fight to the finish on a race course of water.

“This is just the coolest type of sailing there is because you can do a whole race in 10minutes and then go back and do another one,” Don said.

The Wilsons compete and win on waterways across the country. Sometimes together and sometimes against each other.  In the Chicago Match Cup Race of 2012, it was Brother, vs. Sister.  Jennifer’s crew was skippered by two time Olympic Champ Sally Barkow and the only all-female team competing.

“Always in our family there is competition about absolutely everything,” Jennifer said.

But there was no competition when the duo launched the Chicago Match Race Center in 2009. It’s a premier world class sailing center right on Chicago’s lakefront.

“So match racing is something that goes on all around the world but there was not very much of it in Chicago,” Don said.

Until Don came along! As CEO of  one of the city’s biggest proprietary trading firms, DRW Holdings, Don put his money where his mouth is, and created this center with hopes of bringing world class match racing to the shores of Lake Michigan.

“Well for me this is a rest because you can`t think about anything else. You have to totally focus on it,” Don said.

With young sailors flocking from across the globe, this summer alone, there are interns from New Zealand, Bermuda and the West Coast, this center helps keep match racing alive alongside a cement jungle.

“It’s probably one of the coolest things going on right now both locally regionally and nationally,” said Match Race Center Director Tod Reynolds.

Reynolds got involved with the Match Race Center while a student at Northwestern University. After going back east and working as an electrical engineer, the water and his respect for the Wilsons called him back to Chicago.

“There’s lots of individuals involved in sailing and to buy a mega yacht or to buy a big beautiful boat that you can see around the harbor here, and I think what Don has chosen to do here in the city is really really unique and something that you can give back to the community,” Reynolds said.

The Wilsons started the Chicago Match Cup four years ago. It’s become one of the premier us sailing events in the world. Two years ago it became apart of a world tour. This year it coincides with the historic tall ships festival at Navy Pier.

And again, the brother and sister duo will compete on the same team.

“There`s just not a lot of other set ups like this in the world. So this definitely is a great thing for Chicago, for people who are interested in sailing,” Don said.

Don and Jennifer Wilson — two of Chicago`s Very Own.

The Chicago Match Cup runs from August 6-11. There you`ll see the Wilsons compete against other sailors.

The Match Cup Race is in conjunction with the Majestic Tall Ships Festival.

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