A champion of waterfront eccentrics

The industry lost one of its most authentic voices and ardent practitioners late last year with the death of Jack Sherwood.

The industry lost one of its most authentic voices and ardent practitioners late last year with the death of Jack Sherwood.

The former newspaper columnist turned marine magazine writer and his beloved 22-foot Erewhon, a Sparkman & Stephens-designed sloop, were familiar sights on Chesapeake Bay, especially around Annapolis.

For nearly 20 years Sherwood wrote a monthly column for Soundings magazine called “Bay Tripper,” along with other stories. I hired and edited this endearing curmudgeon, who was, in his own words, a “cheapskate rag hauler” and proud of it. But Sherwood was far too complicated to be captured in a cliché.

A consummate small-boat sailor, Sherwood was a skilled storyteller who had a special talent for writing about the offbeat waterfront characters who bring so much color and life to our watery world.

He wrote with affection about the workers who keep boats of all ages and denominations humming: riggers, painters, mechanics, boatwrights and other assorted boatyard characters, such as the late “Budweiser Dave,” an Annapolis yard worker who was one of Sherwood’s favorites.

I fondly recall his columns about Capt. Freddy, the homeless sailing veteran of the Florida Keys, and the ones on a former Washington, D.C., lawyer and liveaboard who kept popping up at anchorages in his junk boats until he (and his junks) finally disappeared.

What impressed me most about Sherwood was this: He found value in the dreams and work of those overlooked denizens of the waterfront, and he gave their lives and stories dignity through his columns.

He championed scruffy down-on-their-luck dreamers who were likely to fall short of their aspirations but never fail, not in Sherwood’s eyes. In the process, the frugal, straight-talking Sherwood became as distinctive and out of the ordinary as the people he wrote about. He was an original.

Sherwood refused to swallow the anchor. He continued to sail Erewhon until this past summer, when he became ill. He died in December at age 84.

The industry will be fortunate if it can keep the boating boomers on the water for as long as Jack Sherwood stayed with his classic 1962 Sailmaster, which he purchased in 1985. It was nothing short of a love affair.

“Erewhon has been my companion and partner for 28 years,” Sherwood told me two years ago, when I turned the tables on the lifelong reporter and interviewed him.

“My late wife called it ‘that stupid boat.’ Even today, I visit with her almost every day and day-sail at least four times a week in season, although I no longer sail her in winter. Erewhon has also taught me how to do many things, among them painting, sanding, varnishing and rigging for single-handing, which I prefer.”

He added, “I know next to nothing about outboard motors and have gone through at least six.” That’s an understatement.

With outboards, Sherwood was all thumbs — or worse.

“Jack went through a new outboard every few years, mostly due to his inability to understand basic outboard mechanics,” says longtime friend John Barry, a retired schooner captain and broker who lives in Oak Island, N.C. “Like the time he stuck an ice pick up the clogged pee hole [tell-tale] on his outboard and broke the tip off inside, which totaled his 1-year old outboard. It was never-ending.”

Barry and I admired Sherwood for the forthright manner in which he wrote about his boating misadventures, on and off the water.

“I enjoyed laughing at myself,” Sherwood said. “All the blunders and mistakes and corrections I made. And a few ‘close shaves.’ One shipwreck, one dismasting, a few nasty storms, once falling overboard, and a near collision with a tugboat pushing a huge barge.”

During the three decades he sailed Erewhon, Sherwood was continually involved in one boat project after another. He tinkered and tweaked and fussed over the boat.

Barry says he was “awestruck” by the intricate, innovative modifications Sherwood made to his small boat to improve single-handed sailing.

“Erewhon looked simple to observers,” Barry says. “It was anything but that. It had more bells, whistles, paint and varnish than a Hinckley.”

Jack Sherwood started in newspapers in 1960 and spent nearly 20 years at The Washington Star as a columnist and feature writer. Even after he left dailies to write for boating magazines, Jack remained, at heart, an old-fashioned newspaperman. He was an accurate reporter, with a good ear and good instincts, and he always made his deadlines.

Before Sherwood passed, his friend Barry found a good home for Erewhon. Barry arranged for the boat to be sold to Winston Groom, the Southern novelist and nonfiction writer who created Forrest Gump; Sherwood and Groom had worked together at The Washington Star and were friends. Erewhon is now turning heads on Mobile Bay, Ala.

“Jack could not have been happier,” Barry said.

This article originally appeared in the February 2017 issue.


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