Kapos: An unlikely sailor takes on ‘The Mac’ adventure

A self-described out-of-shape real estate attorney, Matt Gallagher is unfazed by the challenges that lurk on the choppy waters of Lake Michigan.

“I don’t have the most adventurous career, so sailing is exciting. You go out and you don’t know what the weather conditions will be, and you face them with your family and your friends. It’s about the race and the adventure and the destination,” says Gallagher, a partner at Gallagher Niemeyer & Abrams.

He’s among the many part-time sailors competing in this weekend’s Chicago Yacht Club Race to Mackinac, a 333-mile annual yacht race that ends at Mackinac Island in Michigan.

“The Mac,” as the race is known, is said to be the oldest annual freshwater distance race in the world. It started in 1898 with just five boats. This year’s race has 350 entrants and some 3,000 sailors.

Gallagher grew up in Oak Brook playing soccer and dabbling in theater as a teenager. He earned a bachelor’s degree in government and international studies from Notre Dame, worked for a time for Congressman Harris Fawell and then got a law degree from DePaul University.

After college, he says, “a buddy bought a boat in Lake Geneva so I learned how to sail with his family.” He enjoyed it but didn’t take up the sport in earnest.

That changed about 10 years ago when Gallagher and his wife, Emily Gallagher, principal consultant at Environmental Resources Management, considered buying a vacation home but purchased a boat instead. “We haven’t looked back,” he says.

The Gallaghers sail “The Mac” every year with the same group of friends. Their young children, ages 8 and 6, are learning the sport and will one day join the race, their dad says. For now, they’re enrolled at the sailing school at the Chicago Yacht Club’s Belmont Station where the Gallaghers keep their two boats. They’ll sail the “Endeavour” this weekend.

The race is especially exciting this year, says Gallagher, because records could be broken — though not by him. His boat will be in the cruising division, which takes off out of the downtown yacht club harbor on Friday. The faster boats set out Saturday.

Gallagher and other competitors will be watching Great Lakes sailor Rick Warner, who recently purchased “Arete,” a 60-foot-long, 61-foot-wide Orma 60 that’s expected to shatter records. Vessels like Warner’s can cost as much as $5 million.

“Most boats aren’t that sexy, so it’s going to be fun to see what happens,” says Gallagher.

Previous Mac records were set by the late Steve Fossett, who won the overall race in 1998 in 18 hours, 50 minutes with a catamaran, and the late Roy Disney, who set the monohull record in 23 hours, 30 minutes in 2002.

A ‘Cirque du Trump’ viewing party

Some of Chicago’s most noted left-leaning political junkies and consultants have organized a private gathering to watch Donald Trump take the stage Thursday at the Republican National Convention.

Becky Carroll, who’s co-hosting a downtown gathering of Democratic insiders, equates the GOP gathering to “a circus.” And invitations play off that view with the heading “Cirque du Trump” and a caricature of the New York billionaire in a baseball hat (of course) juggling an elephant while balancing on a unicycle.

It’s all fun but the convention is serious business for Carroll and other party organizers.

She was national director of Women for Obama in 2008 and now is president/CEO of C-Strategies. Carroll’s co-hosting the Trump watch party with Dave Lundy, also a left-leaning political consultant and strategist. He counts J.B. Pritzker, a supporter of Democrat Hillary Clinton, as a client. “It will be fun to be with like-minded people — including some Republicans,” says Lundy, who will attend the Democratic National Convention in Philadelphia later this month.

Others on the private party list expected to attend include Jason Erkes, former president of Chicago Sport and Social Club and a long-time behind-the-scenes player in Democratic politics; Jeremy Bird of 270 Strategies and an alum of campaigns that helped elect President Barack Obama; Michael Ruemmler, who managed Mayor Rahm Emanuel’s mayoral re-election; and Anne Szkatulski, a former legislative aide to state Attorney General Lisa Madigan.

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