It’s a sunny Saturday in late May, but the Eldean Shipyard in Macatawa, Michigan, is nearly silent. Inside a metal storage facility, a massive black sailboat sits in a cradle nearly three stories high.

It’s called il Mostro (Italian for “the monster”), and there’s a reason for that. The height of the mast off the water is more than 100 feet. Dangling from the bottom of the boat is an enormous white pole—a stainless steel and lead canting keel—which looks like a 12-foot clock pendulum with a torpedo attached to it. For years this Volvo 70 raced around the world with ocean sailors, and it is still considered one of the fastest distance monohull sailboats ever built.

Yellow scaffolding surrounds il Mostro. It wiggles slightly as Peter Thornton, who owns the yacht, and a few others walk the spiraling ascent into the air. The boat is so wide at 18.5 feet that it needs two steering wheels positioned on either side. Sometimes it takes six men to turn a single winch, a drumlike device that pulls in the lines for the sails. “It’s a rocket,” says Thornton, who won the coveted Royono Trophy at last year’s Race to Mackinac by being the first to finish. “And it was just sitting in a boatyard with so much potential. People are spending millions upon millions of dollars to build fast sailboats. If all you are looking for is outright raw speed, this is the boat.”

The boat is painted in the shape of a shoe, with red straps and gray treads. Once it was adorned with PUMA logos, now removed at the request of its original sponsor. In place of one of the logos, Thornton had a jagged pumpkin face painted on the boat with a pair of menacing eyes. Even in daylight, the stark white face glows against its ebony background like it’s warding off competitors.

“I’m far from being the greatest sailor in the world, but I’m probably one of the most enthusiastic,” says Thornton, a longtime member of the Chicago Yacht Club. “I love taking old boats and seeing what they were, what they could be, and then executing that.” That’s exactly what Thornton has done. With significant changes made to il Mostro in the offseason, he now hopes to sail the fastest Race to Mackinac—from Navy Pier to Mackinac Island, Michigan—this July by beating Roy Disney’s 2002 monohull record of 23 hours, 30 minutes, and 34 seconds. “I’m running out of track,” says Thornton, who is 73. “If I don’t do it now, when would I do it? I’m still reasonably healthy, and this is such an exciting boat.”

Back in Chicago more than 150 miles away, students from Rickover Naval Academy in Edgewater are pursuing another challenge: learning how to sail and race in Belmont Harbor.

Senior Martin Heft, who wears a T-shirt that says ONLY THE STRONG SURVIVE, jokes that he joined the team four years ago because he mistakenly thought it would be an easy extracurricular activity. “Before sailing, I stayed home and played video games,” Heft says. “Now it’s a race to get my homework done, go to the harbor, and sail. It’s become my passion.”

But learning to sail didn’t come easily, especially for someone who had never been on a sailboat before. On the first day of practice, Heft was put in a boat and told to steer. “It was one of the scariest things I had ever done,” says Heft, who’s been Rickover Naval Academy’s sailing team captain for the past three years. “But I learned.”

Most high school sailing programs are stacked with athletes who come from upper-class backgrounds, attend elite prep schools, and have grown up around the sport. That’s not the case at Rickover Naval Academy. Nearly 85 percent of its students are considered low income and more than 70 percent are Hispanic, according to Chicago Public Schools’ website. “Up to this point, there’s been very little opportunity for Chicago Public School kids to get out there and do a sailing program,” says Commander Mike Tooker, who works with the sailors at the academy. “It’s so expensive, and it’s in an environment that is not normally accessible to the less well-to-do who are in the lower to middle class.”

Giving access to these students is helping diversify the sport while allowing them a chance to network and gain leadership skills and important business knowledge. “That’s why what the Chicago Yacht Club Foundation is doing is so remarkable,” Tooker says. “We aren’t just introducing a sport, but an entire doorway to opportunities by giving them the chance to rub elbows and meet people they never would have had a chance to meet.”

A few years ago the foundation began inviting girls from Chicago public schools like Rickover Naval Academy to write essays using sailing as a metaphor for life. The authors of the best essays, which are generally about overcoming adversity, are then sent to Sisters Under Sail, a nonprofit leadership program based in New Jersey that helps girls and women learn to sail with an all-female crew on the 110-foot-long Unicorn. One of them, Rickover Naval Academy senior Itzel Lucio, says, “It empowered me to think beyond my expectations, especially since I come from a background where women are [told they’re] meant to be at home.”

That’s also the reason Chris Mitchell, the former director of sailing at the Chicago Yacht Club and a trustee at the Chicago Yacht Club Foundation, approached Rickover Naval Academy about starting a sailing program that would be funded by the Chicago Yacht Club Foundation. “Sailing doesn’t tend to be a sport that people just start to do out of the blue,” Mitchell says. “Many of these students have never even seen a boat or the city of Chicago’s skyline. It’s a foreign concept for anyone who comes in from the outside.”

That’s a sentiment Heft knows all too well. He says it’s been a story of “David versus Goliath” when sailing against other schools like New Trier, St. Ignatius, and Walter Payton College Preparatory. He jokes that these schools come to races with more boats and enough sailors to have alternates who can rotate in and off the water. “They wanted to win,” Heft says. “My biggest goal was getting through my first race without capsizing.”

During all of his early races, Heft finished in last place. At one point Heft suffered a concussion from hitting his head on the boom. When he finally finished his first race without capsizing, he says, “it was the best feeling getting to go home with a dry head.”

Small victories led to bigger ones. After four years of sailing, Heft finally won his first race this year as a senior. But Heft’s racing career would never have happened, he says, had it not been for the Chicago Yacht Club Foundation, which paid for Rickover Naval Academy race entry fees, PFDs, sailing dry suits, gloves, and boots, and donates a volunteer coach and the use of the sailboats. Without the foundation’s assistance, Heft says, he wouldn’t be the same. “It’s changed all aspects of my life, and the only thing I ever want to do anymore is be at the harbor on the water,” he says.

Although worlds apart, both Heft and Thornton share the same passion for sailing. Thornton’s love of boats started as a Sea Scout while growing up on Chicago’s South Side. He recalls how the idea of owning a boat seemed “so far out of reach.” Still, the Mendel High School grad vowed to make it happen someday.

Years later Thornton made good on that promise and purchased his first boat, a 1939 Chris Craft wooden powerboat, with a friend. After graduating through other powerboats, Thornton started sailing more than 35 years ago. In 2005, Thornton won his first of two Royono Trophies, racing a Great Lakes 70 sailboat named Holua. After winning the largest annual freshwater race in the US, “I thought I was out,” he says. “I wanted to spend time with my wife.”

Years passed. Two years ago, some of Thornton’s old sailing crew asked him to consider sailing again. “I told them the only way I would do it is if I could get something that would break the Mac record,” Thornton says.

That’s when his sailing buddies suggested buying il Mostro, which had been sitting in a boatyard in Providence, Rhode Island. Thornton considered buying a few other boats—including Disney’s Pyewacket, which set the record he hopes to beat—but decided against it.

The bigger challenge was getting il Mostro back to the Midwest. With a 16-foot draw (the depth of water needed to safely clear the bottom), transporting il Mostro through most canals was nearly impossible, and after purchasing the boat in late 2011, Thornton ended up doing the unthinkable: He had his crew remove the keel before sailing up the Hudson River and down through the Erie Canal, then re-added it in Oswego, New York, and sailed through the Great Lakes to Chicago. “I don’t think anyone else is crazy enough to go through what we did,” Thornton says with a laugh.

Like most sailors, Heft knows of il Mostro and Thornton’s quest to break the course record for the Race to Mackinac. “That’s a pretty good record that Roy Disney set,” Heft says. “For any single-hull ship, even il Mostro, to try and beat it would be astonishing, if not impossible.”

Thornton knows he needs every bit of luck and the right weather conditions to position il Mostro. For more than half the race during last year’s Mac, il Mostro averaged more than 11 knots (12.7 miles per hour), putting it on pace to beat the record. “We were clipping along at 12, 13 knots, and all it had to do was keep blowing,” says Thornton, whose crew last year included Ken Read, one of the world’s most accomplished sailors. “And the wind quit. It went dead.” Il Mostro still finished nearly an hour in front of his nearest competitor, Windquest, a Max Z86, but more than 12 hours behind Disney’s record. So after last year’s race, Thornton worked with il Mostro’s previous ocean sailors, who raced around the world, to “define where the boat had weaknesses.”

Then, three major improvements were made to il Mostro. The boat’s overall weight was reduced by more than 500 pounds, mainly by removing a secondary generator. The most forward part of the boat, the bowsprit, nearly doubled in size to make it faster. A larger mainsail, with approximately 18 inches at the top, was added so it can capture faster-moving air that is higher up. “This boat is not the same boat it was last year,” Thornton says. “We’ve done some things to speed it up and make it more user-friendly.”

Down below, the cabin, which had previously looked like a coal mine, was repainted white. The inventory of sails was enhanced. The hull and keel were cleaned, sanded, and repainted, partly to reduce drag, since any imperfection can make a small difference. “We fight for tenths of knots,” Thornton says. “You’ve got to be very, very picky and look for every little opportunity to reduce drag. That’s what it’s all about.”

How much those changes will improve il Mostro’s chances for breaking the Race to Mackinac’s monohull course record remains to be seen. “There’s a lot of speculation,” says Greg Fordon, who raced on il Mostro in 2012 and supervised the offseason changes in Michigan, “but I think il Mostro has better potential than any other boat to break the record, if we have the right weather.”

As passionate as Thornton is about improving il Mostro and chasing sailing records, he also hopes to inspire others, especially Chicago youth, to love his sport. “It’s kind of selfish if you just keep this to yourself,” Thornton says. “I think you should, if you can, expose young people to the sport, to the lake, and to the yacht club.... It might [spark the thought], ‘This might be something I want to do someday.’” Last summer Thornton invited Paola Morales, a senior at Rickover Naval Academy, and a dozen or so students to sail on il Mostro. “It was really cool,” Morales says. “It was so exciting to feel that adrenaline when you reach so far down by the water and come back up.

Unlike his classmate, Heft hasn’t been on il Mostro, but he is fascinated by Thornton’s quest and hopes to pursue his love of the sport. “If it weren’t for sailing,” he says, “I’m not sure exactly what I’d be doing right now.” After graduating from Rickover Naval Academy this summer, Heft will spend his time working for the Chicago Yacht Club. And like Thornton once did, he also hopes to someday own his own boat and compete alongside sailors in that great freshwater race. “I hope,” says Heft, “to meet someone this summer so I can be on a crew that sails the Race to Mackinac.”

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