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Skipjack: The Story of America's Last Sailing Oystermen

Sep 14, 2012 11:06AM ● By Anonymous

No outsider to Deal island knows this more than their skipjack rivals, the tilghman islanders...except, perhaps, author christopher White.

White spent several years living on tilghman island while researching his book Skipjack: The Story of America’s Last Sailing Oystermen. He befriended the few remaining skipjack captains, worked the boats, and for one adventurous weekend, crewed aboard the skipjack Rebecca T. Ruark with captain Wade Murphy, Jr. for the annual race, held in the remote waters off Somerset county. To view the race from shore is relaxing leisure. To participate onboard is rigorous exercise of sisyphean proportion. White captured the arduous race and its magnitude in chapter two of his work. He weaves a darn fine tale from his experience.

And last September, we sent photographer coleman Sellers to also capture the thrill of racing firsthand. He spent the day aboard the Somerset with captain Walton benton. We think White’s excerpt matches quite well to Sellers’ photography in this stunning example of the vanishing craft of skipjack racing. Enjoy.

—James Houck


Skipjack: The Story of America's Last Sailing Oystermen

Chapter Two: At the Races

For Chesapeake watermen, all news begins with the wind. Good or bad, all forecasts, all tidings, float in with the breeze. Whether a skipjack captain can work on a given day, whether he can lie low, is determined by the speed of the air. Upon waking, a waterman listens to the night. If it’s too quiet or too fierce, he might catch a few more winks. But if the morning sounds promising, he rushes to catch the first breath. By dawn, each gust brings the expectation of a good harvest. His prospects, his day, will be shaped by the wind. A seasoned skipper plays this breeze to his advantage, reading every nuance, harnessing every whim. Above all, his fellow fishermen measure him by his prowess with the wind.

At no time was this truer, I thought, standing on the bow of Rebecca, than on this day, the first Monday of September. The Labor Day Race at Deal Island was getting under way. We had sailed ten hours south to Deal, home of one-third of the skipjack fleet, the day before, affording us a chance to check the rigging. That fifty-mile voyage was about the range of a skipjack. Now, after a poor night’s sleep on the deck of Rebecca, we were making for the start of the race. All entries were required to rendezvous at the race committee boat northwest of the island at 10:00 a.m. sharp. The gun and flag that would mark the start of the race were still more than forty minutes away, yet the sun was already high in a flawless blue sky.

The wind had swung clockwise during the night. The southerly breeze of the afternoon before had turned west and was blowing northwest by morning. And it kept turning. Even now, the wind was breezing up nearly due north, right down the length of the racecourse. Ninety percent of all skipjack races are won “on the wind”; that is, facing the wind. So, with the wind parallel to the course, it was shaping up to be a good race day. Blowing nicely, too—about 20 miles per hour—and that was good news for Rebecca: She sailed best in heavy air. Poor news for smaller boats like Esther F., with Bart Murphy at the helm.

It was thirty-two minutes before the start when we passed the channel buoys that marked the entrance to Deal Harbor. Wadey began barking orders. He was on edge. Racing brought out the worst in him, and he took it out on the crew. “Heist the sails, boys,” he shouted, “and be quick.” Wadey then turned the bow north into the wind. Four of us hauled the main, which rattled up the mast with the aid of classic wooden hoops, and secured it with a fast-releasing slip knot; two others handled the jib. The jib halyard twisted and the whole thing had to be downhauled, set right, and raised again. “Jesus Christ,” snapped Wadey. “Get it right, goddamn it.” The wind was to blame, not the crew.

Wadey’s racing team comprised serious amateur sailors who crewed for him every Labor Day. The only watermen were cousin Lawrence Murphy and Hunky Lednum. The others were Jack Dunham and Fred Whittaker, both of Wilmington, and Ray Saunders and me from the western shore. Li’l Wade, eighteen years old, the captain’s son, made seven. Wadey’s advice to the crew was simple and brief: “Everybody keep their heads down after the start. Unless something needs fixing, I don’t want to see anybody. For heaven’s sake, keep out of my goddamn way.”

Racing was a blood sport to Wade Murphy. For years aboard Sigsbee, a “dumb” boat, he had lost race after race. Now, with arguably the smartest racing boat in the skipjack fleet, he had something to prove. With the sloop’s only real competition, Kathryn, not appearing at the Deal Races this year, it was Wadey’s race to lose. There were no other fore-and-aft- planked skipjacks at the race. The cross-planked boats were decidedly slower, unless a lucky captain caught a puff of wind while Rebecca was in dead water. Bart was hoping for just that, but it hadn’t happened on a Labor Day yet. Wadey had caught good breezes and won the trophy the last two years.

Dredge-boat captains had been racing one another since the dawn of oystering on the Chesapeake Bay. In the early days of schooners and bugeyes, the dockside price for the day’s catch fluctuated hourly. Consequently, captains would race one another to port to get the better price. Later, when skipjacks were born and joined their larger and faster cousins on the oyster rocks, buy boats anchored near each fleet to buy oysters at midday. Captains raced to these buy boats every time their decks were filled. It became important not only to have a good dredging boat but a good racing boat as well. Soon, skipjack captains began matching their boats for the sheer joy of it. And their reputations as skippers depended as much on their successes in racing as by the number of bushels they caught.

In 1960, Ben Evans and Clifton Webster of Deal Island approached the local Lions Club and persuaded them to create a homecoming event on Labor Day, complete with a skipjack race. Thirty captains showed up, and the races have run annually ever since. They now come with a combined purse of $1,750 for the first three finishers, provided by sponsors, mostly local newspapers and banks. During the first thirty years, the winningest captain was Stanford White Jr., whose F. C. Lewis won ten times. The next most successful captain was Orville Parks, considered the finest tactician, with four wins. At least a few Tilghman boats traveled to Deal each September to try to take the trophy away from the local captains. The rivalry between the two islands became intense. So far, most years the Deal Islanders have kept their trophy at home.

But last year was a different story. The Labor Day Races got off to a poor start, or rather a contested one. That Monday, at ten o’clock, the only boat at the starting line was Rebecca. It was the official time for the start of the race and Wadey was ready to go. The seven other captains, comprising Bart Murphy and six Deal Islanders, were late getting to the committee boat. Wadey started without them. He rounded the course and crossed the finish line, an eight-mile run (an extended course), before many had set their sails. Rebecca was given first place, but the Deal Islanders disputed the win and have been complaining about it ever since. The central argument revolved around whether a race starts when the official time passed or when the gun was fired.

Just this morning before we got under way for today’s race, one of the Deal captains, Ted Webster of H. M. Krentz, had berated Wadey for last year’s debacle.

“If it had been me at the starting line, I would have waited for you,” Ted had said. “Don’t you have any principles?”

“Yes,” Wadey answered.

“So why don’t you use them. Nobody farred the gun.”

“When I race I’m serious, Ted, and 10 o’clock is 10 o’clock.”

“You should have waited. If it had been a fair race, I would have beat your ass.”

“How much air do you think I need to win?” Wadey asked, referring to Rebecca’s proficiency in heavier weather.

“Twelve or fifteen mile,” said Ted, abbreviating miles per hour, “and it was blowing light and I would have beat you. And you knew it. That’s why you jumped the start.”

Wadey pushed his cap back on his head and said, “Well, it’s blowing today, so try to get to the start by ten o’clock, and I’ll beat you again.”


From Skipjack by Christopher White. Copyright © 2009 by the author and reprinted by permission of St. Martin’s Press, LLC.

Chapter Two continues with the full account of the day’s proceedings, including the amazing finish of the main race. To order Christopher White’s book Skipjack: The Story of America’s Last Sailing Oystermen, visit