Wisconsin Marine Historical Society

Lessons learned from sailing — the hard way

August 7, 2020
Mad Cap Final

By Carl Eisenberg

My love affair with the sea started long ago, and far, far away, when as a three year old redhead, my parents took me on a big cruise boat. I don’t remember much about that trip, but I’m sure my parents remembered it for a long time. I can imagine that we all had to walk up a gangplank to board the ship. I was a curious little boy, and I watched the man who pulled the pin to close the gate on the ship once the gangplank was removed.

The ship pulled away from the pier and we were on our way. While the grown ups were distracted, I fiddled with the closed gate and opened it. This left me standing at the edge of the deck with nothing between me and the dark sea. I actually do remember looking down directly into the water. To my surprise, my mother screamed, I don’t know what, but I can imagine now, and rushed to grab me before I fell to my certain death in the water. She harnessed me for the rest of the trip. Later in life –– and we will get to that –– experiences taught me to respect the water.

In 1984, my wife Susan and I visited an outdoor booth, sponsored by the Wisconsin Marine Historical Society, at Milwaukee’s Maritime Days. By that time, we were sailors and decided to join WMHS if for nothing else but to support the group. We didn’t do much more than attend WMHS-sponsored social, like its annual Christmas tree ship dinner. We had fun talking with people who enjoyed boating, sailing, diving, collecting things and marine history. We had fun at these events for years, but, honestly, our attention was focused on our children and my job. Our children were active in sports, some of which took us all over the country and my job took a lot of time including leading the Wisconsin Chapter of the American Academy of Pediatrics, and the Legislative Council of the Wisconsin Medical Society.     

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Why my interest continues has to do with events that started when I was about fourteen. My father had bought a speedboat as a gift to his brother. Eventually, the boat ended up as our boat and I learned how to do racing turns and entered and won a speedboat race in Cleveland, Ohio, where we lived.

I took my dad for a ride and demonstrated the special sliding racing turns. Well, that was another not-so-good idea, because a big wave came over the boat and landed on my father’s head during one of these turns. Needless to say, the boat then disappeared from my life, and I found myself enrolled in sailing lessons. This was one of the best things that ever happened to me. Somebody must have noticed me, because I was asked to help an older couple deliver a Shark-class sailboat from one yacht club to another, a distance of about ten miles. All went well and I was feeling pretty good, until a squall came up suddenly with strong winds that shreddedthe jib sail. That was the first time I was scared on a sailboat.

We successfully delivered the boat, but I carry the image of the shredded jib sail with me to this day. This fear converted to respect and taught me to pay attention to weather forecasts. My love affair with water became a love affair with sailing. Early in my sailing lessons, I got to crew on a six-meter class sailboat named MADCAP, owned by Mr. Lew Kershaw.  At that time, MADCAP had a small cabin and was more of a cruising than a racing vessel. The owner’s daughter was one of my sailing instructors. I got to clean the bilge and learn by observing the decisions Mr. Kershaw made. This experience stuck with me, and when I retired, I decided to try to find MADCAP on the internet. Success: Mr. Kershaw’s daughter had taken MADCAP to North Carolina, sailed her there for years, and then sold her to someone on the east coast who restored the vessel to a racing design.

It seems like it happened overnight, but several years later during my education and post-graduate years, there were some sailing adventures that kept alive my interest in sailboats and water.

One summer, I was working at Massachusetts General Hospital. My boss, Dr. Hugo Moser, studied the diagnosis and treatment of the congenital biochemical disorder portrayed in the movie, Lorenzo’s Oil.During my free time I sailed on the Charles River out of the Boston Community Boating facility, similar to the Milwaukee Community Sailing Center.

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Another time, one of my medical school classmates and his wife spent a winter building a new mast for his sailboat. The mast was beautiful. In the spring, Bill wanted to try out his boat. We drove to the Outer Banks, stepped the mast while the boat was still on the trailer, and he started to drive toward the launch ramp. His wife and I shouted and waved, but he kept going. He hadn’t noticed the electric wires which caught onto the mast and shattered it. Another lesson learned — look up!

Later, when Susan and I were in Portland, Oregon, where I was in training at the University of Oregon Hospital, we bought a plywood sailboat, a Geary 18, otherwise known as a Flattie because of its flat bottom. We raced that boat on Vancouver Lake, just north of Portland, across the Columbia River in the State of Washington. We had fun and made a lot of friends. We sold the Flattie as we prepared to move to Wisconsin. Before we left, I called what was then Vanguard, now Harken, and ordered a US 470, an Olympic class, racing dingy. While driving to Milwaukee, one of our Flattie sailing friends phoned us with bad news. During one of the races, a storm struck, and one of my friend’s Flattie capsized. Friends  tried to find him, but couldn’t. If he had had a whistle maybe he would have been rescued. I always have a whistle now when I sail.

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My years in Milwaukee involved being a husband, father, pediatrician, and member and leader in state and national pediatric organizations. We had time to sail a little, and again, I scared my mother. This time, not long after our first daughter was born, my wife and I decided to intentionally capsize the 470 to be sure we could get it upright again. We chose a small, shallow, inland lake, gave my daughter to my mother who stayed on shore, took the 470 out a little way and capsized it. My mother was terrified. I hadn’t changed much since I was three years old, still naughty!

The next sailboat was a 19-foot Flying Scot which we sailed out of the Milwaukee Community Sailing Center for a while until the children got busy with other activities. I resumed sailing after I retired, giving sailboat rides to Sailing Center visitors. In 2018, I developed “sailbirding” for my birding friends. Several other experienced skippers and I took small groups of birders, with binoculars and cameras, to look for shorebirds on the Milwaukee breakwater.

During my retirement years I’ve become a volunteer for the Wisconsin Marine Historical Society and serve as its president. Leading the group has become a whole series of personal lessons — but that’s a story for another day.

Photo: This is what MADCAP looks like today. (Credit: Mark Krasnow Photography)


Carl Eisenberg is a sailor and birdwatcher, and served as president of the Wisconsin Marine Historical Society from 2016 – 2024. A retired pediatrician, he is a graduate of Duke University School of Medicine. He lives in Mequon, Wis.

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