When I read about Ben Ainslie’s frustration in sailing underneath New York City (literally) in the Louis Vuitton America’s Cup World Series in May, and knowing that Chicago was coming up next in June, I thought there was a real chance of him throwing the baby out with the bath water – in this case Lake Michigan, which is sort of bathtub-shaped.

I hail from Chicago – ‘Captain Haddock’s fresh water pirate’. Having grown up sailing dinghies in Belmont Harbor on the near north side shore, I remember the frustration of offshore winds whistling through high-rise buildings catching you off guard – worse when we sometimes capsized in those non-rightable boats during frostbite series in early March when the lake ice was still on the way out.

This was well before sailors used wetsuits or drysuits or any specialised sailing clothing so those painful experiences surely sharpened our senses for abrupt wind changes in view of staying dry. Those semi-survival lessons have stood me in good stead for a lifetime of all sorts of changing conditions on the far side of the world.

What must have been more of a concern for the organisers of the Louis Vuitton Series than variable winds whistling through skyscrapers – now two and half times as tall as when I sailed there – is Chicago’s notorious light to non-existent winds in summer.

The Chicago World Series event drew crowds of 200,000 and provided genuinely spectacular racing on the city-side lake course. Credit: Ricardo Pinto.

Becalmed in front of the city

When I was older, racing keelboats, I can remember countless hours becalmed in front of that city. This always provided a ready excuse to sit on the pushpit looking for zephyrs off the end of a cigarette. A similar urban vacuum proved to be the case on the Saturday, day one of the two-day Louis Vuitton event.

Luckily, a northerly kicked in for the Sunday, creating the spectacle needed for the punters on Navy Pier, which is arguably one of the best venues for a big city public to hold witness.

Let’s face it though, a motor boat race would be more of a sure bet to satisfy the media and the crowds than a yacht race with all the usual unpredictables that make yacht races so interesting, at least for those of us who take part in them.

But in spite of half the event being a wash-out what turned into a one-day race event was a resounding success, which is great news for the ‘Windy City’. Organisers take note: the sobriquet ‘Windy City’ does not relate to wind alone; check your Wikipedia.

Punching above their weight

Holding this event successfully was a fitting accolade for freshwater, Great Lakes sailors who, if truth be known, have always punched way above their weight when it comes to many international sailing events on both fresh and salt. Buddy Melges comes to mind, as do the Harken brothers, launching their careers from tiny lakes in Wisconsin.

At a young age I was lucky enough to have been press-ganged into several Corinthian-sailed yachts from Chicago that had stellar ocean racing careers. The owners needed foredeck fodder and I was the one to sort out the tangles up the rig and also jump over the side to put rubber bands on the folding propellers.

Those privileges – going over the side in Lake Superior in May focused my mind to become a navigator as soon as possible – were my one-way ticket out for a life traversing the world’s oceans, but I have never forgotten my Midwestern roots. I was overjoyed to hear that Chicago is firmly back on the America’s Cup map.

Although this stadium racing is all the go, it must be said that the risks for both organisers and sailors are substantial in these big city, urban environments where so much heat – both real and ‘hot air’ – is generated that any breeze at all often goes straight up.

Coupled with too few days that are locked into live media slots seems like a crapshoot to me, and in the end the casino always wins. Next stop Las Vegas?