Family and patriotism buoy Krawcheck’s sailing passion

On a recent summer Saturday morning, as a mild sea breeze blew across Charleston Harbor, Lenny Krawcheck pulled the cover off his Lightning, the first step in getting his three-man sailboat ready for the afternoon regatta. Mr. Krawcheck paused for a moment to gaze across the harbor. His experience told him that the wind would pick up by early afternoon, making it a perfect day for some friendly competition among the 16 entrants in the Lightning-class races that were part of the James Island Yacht Club Regatta.

As his extensive record of wins sailing several different classes of “dinghies” through the years demonstrates, Mr. Krawcheck is always in it to win, but being on the water doing what he loves is its own reward for this native Charlestonian.

“My father sailed,” states Mr. Krawcheck pointing to a photo of a sloop displayed prominently on the wall in his downtown law office. “She was called the Riptide. My dad, Jack Krawcheck, gave the Riptide to the United States Coast Guard during World War Two. The Coast Guard took the mast out of it. My dad was on temporary active duty in the Coast Guard during the war and would go out patrolling the harbor in the Riptide every Tuesday night. I was just a little boy, but I remember it because he’d always bring his children Hershey bars and bubble gum that we would retrieve from his canvas jacket the next morning.”

At the end of the war, notes Mr. Krawcheck, the Coast Guard returned the Riptide to his father who put the mast back in it. “That was the first boat I ever went sailing on.”

While his father, Jack, was the family’s first sailor, his older brother Saul was number two. “Saul was the main reason I took to sailboat racing,” says Mr. Krawcheck. “Saul is the one who really taught me how to sail. He really refined my sailing skills.

“When I was a teenager, I bought my first sailboat, a Moth, with my own money,” continues Mr. Krawcheck. “You get committed when you spend your own money. I really appreciated my first boat. Moths are 11-foot catboats and very lightweight. One of the great Moth sailors back then was my friend and competitor, Randall Swan. He is the best Moth sailor there ever was and probably the best sailor Charleston has ever produced.”

When he was about 15 years old, Mr. Krawcheck and his brother, Saul, bought a Y-Flyer. “These boats became very popular in Charleston,” Mr. Krawcheck says. “At one point, we had 30 to 35 of them here. The sailors were of all ages, but very fine sailors.

“In our first Y-Flyer, Saul and I sailed together,” Mr. Krawcheck continues. “He would skipper the boat and I would crew, then vice versa. I won my first regatta in a Y-Flyer in Jacksonville, Fla. when I was about 16 years old. I’ll never forget it.”

For many years, Mr. Krawcheck continued to race Y-Flyers, except during the time he spent at Duke University and later his days at Tulane University earning his law degree. “I was elected to the S.C. House of Representatives right out of law school and I used my second legislative paycheck to have my own Y-Flyer built,” admits Mr. Krawcheck. “The boat coast $450 to build in 1967. It was wooden and was built locally by Teddy Prause. Mine was probably the best boat he ever built. It was fast and I won my share of regattas in that boat. It was a two-person boat and my wife, Townie, crewed for me for many years. We won one Y-Flyer National Championship together in the early 1980s. I won another Y-Flyer National Championship here in Charleston in the early 1990s, but Townie wasn’t sailing with me then.”

According to Mr. Krawcheck, brother Saul eventually went on to handicap sailing, which involves bigger boats that are given a rating and race against time. One-design racing, Mr. Krawcheck’s passion, involves boats in the same class going head-to-head with every other boat. “The theory is that everybody is sailing the same boat,” he explains, “so it’s the skill of the sailors that determines the outcome.”

In the 1970s, Mr. Krawcheck started sailing a Laser, but by late in the decade he had found his real passion … the Lightning, which he sails to this day. “The Lightning is my favorite sailboat,” notes Mr. Krawcheck. “It was designed by a famous yacht designer named Olin Stephens, of Sparkman and Stephens. The Lightning class has stood the test of time, with almost 16,000 built. Even today, the competition in the Lightning class is worldwide.”

Mr. Krawcheck also still competes in his MC Scow, a singled-handed boat with the option of one crewman. “It’s the only one-design class that’s like that,” explains Mr. Krawcheck. “When it’s blowing really hard, it’s advantageous to put another person on to hold it down.”

Racing sailboats has taken Mr. Krawcheck up and down the East Coast from Florida to Maine, to the Great Lakes and Texas and to places along the West Coast. It’s a passion that still drives him to the harbor as often as possible, to put one of his dinghies in the water and to see where the wind takes him.

All four of Mr. Krawcheck’s children — two sons and two daughters — learned to sail. “They have busy lives and they just don’t do it much,” he says. But he hopes that one or more of his eight grandchildren will one day take up the family tradition of sailboat racing. In the meantime, Mr. Krawcheck has no intention of giving up his passion anytime soon.