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Sisters Christina and Meghan O’Rourke on the deck of Chicago's Columbia Yacht Club on Sunday, July 9, 2023.

Sisters Meghan O’Rourke, left, and Christina O’Rourke have their sights set on someday winning the Race to Mackinac. This year marks 100 years since their great-grandfather John P. O’Rourke won the race — but was later disqualified on a technicality.

Justine Tobiasz

Sisters to sail the Race to Mackinac 100 years after their great-grandfather’s win was overturned

Christina O’Rourke was perched on the bow of a 46-foot sailboat called Skye on a sunny July afternoon as the vessel glided past the breakwalls and into Lake Michigan’s open waters. The excursion was another opportunity for O’Rourke and her fellow crew members to sail before this year’s Race to Mackinac, an annual competition hosted by the Chicago Yacht Club that begins Saturday.

The journey from Chicago’s shoreline to Michigan’s Mackinac Island, sandwiched between the upper and lower peninsulas in Lake Huron, is long and the competition is stiff. Among the other entrants is O’Rourke’s younger sister, Meghan, who will race on the boat Hot Lips.

But for the Glenview natives, this event is not just a friendly sibling rivalry: The race is an opportunity, 100 years in the making, to have a Mackinac trophy back in O’Rourke hands.

Christina O’Rourke sails on boat the Skye on July 9, 2023.

Christina O’Rourke, a 35-year-old Glenview resident who works in advertising at United Airlines, will sail this year’s Race to Mackinac on a 46-foot boat called Skye. She likes the adventure that comes with being perched at the bow of the boat.

Justine Tobiasz

A century ago, their great-grandfather John P. O’Rourke and his brother James sailed the 1923 Race to Mackinac in their small Q boat — a once-fashionable model rarely seen today. The brothers fought their way to an improbable victory on behalf of the Jackson Park Yacht Club. But their glory was short-lived. Months later, the O’Rourkes were disqualified on a technicality.

The story of a great win — and subsequent dismissal — has become family lore.

“To me, the Race to Mackinac was always like this legend that I think we were aware of from a really young age,” Christina O’Rourke, 35, said.

Despite familial connections to the sport, the O’Rourke sisters didn’t start sailing until their mid-20s — and both quickly became consumed by life on the water.

“One thing I love about sailing and why it’s so important to me is because you have land problems and when you go sailing, you leave them on land,” Meghan O’Rourke, 34, said.

“Your whole world kind of shrinks to the size of the boat,” her sister added.

Meghan O'Rourke, standing, and her sister, Christina O'Rourke are seen on the Skye, a boat that will compete in the Race to Mackinac, which begins Saturday.

Christina O’Rourke, seated, and her sister, Meghan O’Rourke, are seen on the Skye, a boat that will compete in the Race to Mackinac, which begins Saturday. The sisters and Skye crew members took WBEZ staff members out on Lake Michigan to demonstrate some sailing maneuvers.

Justine Tobiasz

After introductory courses, hours on boats and feeling steady on their sea legs, the sisters both decided to take on the race they had heard so much about as children. This year will be their sixth time sailing the Mac.

The Race to Mackinac began in 1898 with just five boats, according to the Chicago Yacht Club. In the 125 years since, it has ballooned into what sailing enthusiasts call a bucket list race, which attracts entrants from around the world.

This year’s race, which will include more than 2,000 competitors on about 250 boats, will begin on Saturday just beyond Navy Pier. If all goes well, the sailors will step foot on the island in two or three days, after working around the clock to reach their destination.

Mackinac Race, 1934

The Race to Mackinac began in 1898 with just five boats. In the 125 years since, it has become a bucket list race that attracts sailors from around the world. This photo shows boats in the 1934 race.

At 333 miles, it’s the longest freshwater race in the world and the sheer distance makes the Mac a test of endurance, will and preparation. Winning requires having the right group of sailors with the right set of skills, plus an ability to weather whatever the lake and sky presents, said race chairman Sam Veilleux.

Last year, intense storms propelled boats to the island swiftly.

“I don’t ever want to get up there that quick again,” said Christina O’Rourke.

But when the elements get rough, there is some comfort in knowing her great-grandfather charted the same waters. Christina O’Rourke said she finds herself wondering about him when she’s racing the Mac.

“It does mean a lot to me to have that connection,” she said.

Keeping a family dream alive

The 1923 race attracted 17 yachts, including John O’Rourke’s boat, the Intruder. The comparatively small boat was seen as a longshot to win, but the vessel’s size proved to be beneficial in that year’s weather.

“Intruder, perfectly sailed, meeting good luck, made one of the gamest races of the big fleet,” the Chicago Daily Tribune reported in an article with the headline “Intruder fights waves, rain to capture Mackinac Race.”

Upon reaching land, the O’Rourke brothers sent a telegram to their family to announce their win. “Mighty tired but otherwise in excellent shape.”

A 1923 telegram sent from John and James O'Rourke home to their family

The O’Rourke brothers sent the news of their victory home to Chicago.

But back home in Chicago, their luck took a turn for the worse.

What really led to the disqualification 100 years ago will probably never be definitively known, but according to Chicago Yacht Club documentation from the time, John O’Rourke failed to submit a proper certificate of measurement. That paperwork helps determine each boat’s handicap. Following the race, the host club said O’Rourke didn’t comply with orders to remeasure his boat.

About three months later, the race committee voted to disqualify the Intruder, along with two other boats from Jackson Park Yacht Club. Victory was awarded to a Chicago Yacht Club boat, the Virginia.

Collage of John P. O'Rourke's 1923 victory

John P. O’Rourke and his brother James sailed their Q boat, the Intruder, to victory in the 1923 Race to Mackinac on behalf of the Jackson Park Yacht Club. But their glory was short lived, they were stripped of their victory in October of that year. In the century since, there’s been ample speculation on what really happened.

John O’Rourke accused the committee of unethical practices and favoritism, according to Tribune reporting. But his appeal to the Lake Michigan Yachting Association was denied on the grounds that he incorrectly filed the appeal directly to the association rather than the race committee.

O’Rourke’s descendants have heard a lot of speculation about what happened in 1923, from cheating to gambling on the race. Another well-known claim is the race organizers didn’t like South Side Irishmen defeating the host club. However, Robert J. Wiesen, manager of Chicago Yacht Club’s Race to Mackinac history project, called all these theories “scuttlebutt” and said it was merely a matter of enforcing the rules.

Regardless, the disqualification ratcheted up tensions between the two yacht clubs. But today, a century onward, there’s a sense of camaraderie.

“Nowadays all the yacht clubs work together to support the sport of sailing,” Christina O’Rourke said. “Back then, they were huge rivals.”

In 1936, the commodore of the Chicago Yacht Club tried to woo John O’Rourke back to the Mac, writing in a letter that things had changed since 1923. “Dimly I remember some kind of mix-up which you had with our race committee and while I forget the circumstances, I remember it as one of those things which are not happening much nowadays,” the letter, which was shared with WBEZ by the O’Rourke family, reads.

The Skye, a 46-foot boat, on Lake Michigan on July 9, 2023.

This year, nearly 250 boats are entered to sail the Race to Mackinac, including the boat Skye, which Christina O’Rourke will compete on.

Justine Tobiasz

Marlon Harvey, the current Jackson Park Yacht Club commodore, hadn’t heard the story of the O’Rourkes possibly being scorned for being Irish, but said, “it sounds like Chicago.”

Today, Harvey said the South Side Club is probably the most diverse in the city, but he’s conscious of sailing’s segregated past and that there was a time when he, as a Black man, wouldn’t have been welcome at the club he now leads. Harvey knows, despite gains, sailing still has a reputation of being inaccessible. There are also some real barriers to entry, like costs, which is why he champions youth sailing programs with scholarships for neighborhood kids.

The O’Rourke sisters are also interested in helping to open the doors to the sport. They want to get more women involved in sailing, which they say is still dominated by men. In fact, they acknowledge their spot in the race would likely shock their great-grandfather.

“I think he would be surprised his granddaughters are doing it and not his grandsons,” Meghan O’Rourke said. “And then he would also be like, heck yeah.”

Meghan O'Rourke sails on the Skye on July 9, 2023.

For Meghan O’Rourke, 34, sailing is like ‘therapy.’ The Humboldt Park resident, who is a third grade teacher, got into the sport in her mid-20s.

Justine Tobiasz

As they prepare to compete on the centennial anniversary of his storied journey, the sisters are pulling for one another.

“I just want to say good luck to Christina,” Meghan said on a recent afternoon at Chicago’s Columbia Yacht Club.

“I’ll wish Meghan the best race as well. Fair winds and following seas to the Hot Lips crew,” Christina offered in return.

Make no mistake, each wants to be the sister to come out on top, but at the end of the day, they’re both on team O’Rourke and they share a lifelong goal of bringing a victory back to the family — no matter how long it takes.

WBEZ’s Lauren Frost and Justine Tobiasz contributed. Courtney Kueppers is a digital producer/reporter at WBEZ.

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