How A FinTech Pioneer Brought America’s Cup Racing to Chicago

At a Glance

  • DRW founder Don Wilson helps bring elite race to Lake Michigan
  • Event marks first race on fresh water in America's Cup history

Chicago’s lakefront seems built for competitive sailing. Deep water near a series of scenic harbors and an active pier sit in the shadow of an iconic skyline, all in a city famous for its wind.

It is not surprising then that the world’s premier sailing competition, the America’s Cup, chose the city and Lake Michigan as the first ever fresh water venue to host a Cup race in the event’s 165-year history.

What convinced America’s Cup officials to finally consider Chicago, a city with a sailing history that goes back nearly as far as the Cup itself, is a combination of an enhanced competitive sailing scene, technological innovation and 21st century marketing needs. And it’s largely the work of Chicago futures trader Don Wilson.

Wilson, founder and CEO of DRW, has sailed competitively since he was about 13. But the road to establishing Chicago as a racing venue worthy of a world-class event began in 2008, when he founded the Chicago Match Race Center (CMRC).   The Center was designed to train top-notch sailors and host match racing events. Over the years, those events began to draw serious competitors from around the world.

“It was great for me. I could hop on my bike and ride down, and sail against people from all over the world, my kids could come watch and participate,” says Wilson, who still competes in events around the globe and is ranked among the world’s top 25 match race sailors.

19th September 2014, day three, repechage, at the Chicago Match Cup.

Don Wilson races in the Chicago Match Cup in 2014.

Match racing is the style that will be on hand June 10-12 off Navy Pier at the Louis Vuitton America’s Cup World Series event. It is one of eight qualifying races leading up to the America’s Cup finals in Bermuda in 2017. Teams from Japan, New Zealand, France, Sweden, the United States and United Kingdom will compete.


Bringing World-Class Racing to The Lake

As Wilson and the CMRC hosted higher level regattas, they eventually attracted a number of World Match Race Tour events, the highest level of match racing outside the America’s Cup.  Those races attracted people involved in the America’s Cup organization.

“Because people had been to Chicago and seen what an awesome setup it is for match racing, the sailing world knew it was a great place to do this, a very nice setup in a beautiful city,” says Wilson.

Americas Cup course

The 2016 America’s Cup World Series Chicago course.

Oracle Team USA won the 2013 America’s Cup in San Francisco, and as the winning team, had the opportunity to decide where to host the next Cup.  Early on, the organization knew they wanted to at least hold one of the qualifying World Series events in Chicago, and perhaps the America’s Cup final itself.

The CEO of that team was Russell Coutts, a five-time winner of the Cup who is now CEO of the America’s Cup Event Authority, which organizes the events.

“I’ve always recognized that Chicago would be a great venue for us,” says Coutts. “And through the process we’ve realized that it’s probably an even better venue than most people thought it would be.  We’re expecting it to be a big success, particularly if we get good wind conditions.”

About Wilson’s involvement, he adds, “Don has been instrumental in bringing the event to Chicago. Of course, he recognizes first-hand what the venue is capable of. He’s a local and he’s a sailor.”



For Wilson, who started DRW nearly 25 years ago while a floor trader at the Chicago Mercantile Exchange, some virtues of sailing can be likened to trading. There is risk involved, decisions must be made quickly and efficiency is at a premium.

Don Wilson Sailing 2

Wilson accepts the Canada’s Cup in 2010.

“The thing that I really enjoy about sailing is that there are a lot of parallels to things I like about trading – risk/reward decisions, thinking strategically,” he says. “But at the same time, it’s also a physical space to do that in, so it’s a nice contrast to standing in the pit trading or sitting in front of a computer.”

Wilson didn’t race his first match race until 2007 at a Chicago Yacht Club event. He lost most of his first races, but fell in love with the format and less than a year ago was ranked the top match race sailor in the U.S.

“I thought it was just awesome because a match takes 12 – 15 minutes and during that period you make so many decisions and risk/reward calculations, and if you disagree on a rule, there are umpires on the water that rule on the spot. It’s really fast paced and very efficient.”

Given the similarities to trading and risk management, it is perhaps fitting that CME Group is the event’s presenting sponsor.

“It’s a sport of managing the risks,” says Coutts. “When you’re on the racecourse and you have more risky strategies you can take that might give you a greater return, but there are more consistent strategies you can take that will give you a better chance for a positive outcome.”


A TV-Friendly Venue

Several factors make Chicago an ideal destination for America’s Cup racing. There is deep water right next to the main viewing platform on Navy Pier; there is the infrastructure of a major city with hotels, a major airport, great spectator areas and, maybe most important, the city’s skyline acts as an ideal backdrop for television viewing.

“Making sure that the visuals are compelling in terms of the boats and the speed and the action on the water is important, but also the backdrop,” says Tod Reynolds, event director for the Chicago race and director of the CMRC. “There really is no better stadium than the Chicago skyline.”

Russell Coutts, CEO, America’s Cup Event Authority

It’s one of Coutts’ key objectives as CEO to make the America’s Cup races more broadcast-friendly.

“There’s no use putting a television product on a blue sea background without reference to other geographical features,” he says.  “It becomes pretty dull to look at. Those factors bode well for Chicago as a venue that can host events in the future.”

Coutts has instituted several digital media tools to make the races more attractive to sailors and non-sailors alike, including TV rights deals that allow the races to be seen virtually anywhere in the world in multiple languages. The World Series race in New York in May was broadcast to more than 170 countries.  The broadcasts also include superimposed graphics of the race course, and explanations of events as the races are happening.  In the works are live sharing of the sailors’ heart rates, a reminder to casual fans of just how physically challenging modern match race sailing can be.

“Under the old format, for some of the positions, if you were fit enough to walk across the room, you were fit enough to race,” says Coutts. “Now you’ve got to be really fit to race on these yachts.”

Tod Reynolds

Chicago race director Tod Reynolds (foreground) on Lake Michigan.

Flying on Water

Beyond broadcast, the races themselves make for a more media-friendly product than past versions of the America’s Cup. Each race used to last between one to three hours with legs lasting around 30 minutes each. Today races last 20 minutes with each leg taking about six.

That is due to a combination of the match racing format, and some major changes in the boats used in America’s Cup races.  Just a few years ago, America’s Cup boats were 72-feet long. The boats used this year are AC45s, 45-foot catamarans that can reach up to 55 mph. They each have twin aluminum hulls and hydrofoils that help lift them out of the water, all while guided by a Kevlar fixed-wing sail. All boats are one design, but each uses its own proprietary technology to gain an advantage, sometimes with the help of aerospace firms.

The tagline on the Chicago race promotional materials read “The Windy City Was Made For This.” There’s certainly evidence of that. Reynolds is hopeful the line sticks when deciding where to hold future America’s Cup events, as well.

“Our goal is, just like with CMRC, start small, keep growing, keep proving, prove that Chicago is the best spot for this type of racing, and hopefully the stars align one day we will see the America’s Cup final here,” he says.

For Wilson, the event marks the culmination of years of developing a first-rate sailing scene in Chicago. When he began match racing less than a decade ago, he did not see this day coming.

“The America’s Cup definitely wasn’t something I was thinking about at all when we started the sailing center, but it was a pretty cool outcome.”

Evan Peterson is director of corporate marketing at CME Group and managing editor of OpenMarkets.

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