J. Michael Winston; Avid Yachtsman and Racer

J. Michael Winston raced up and down the East Coast and across the Atlantic.
J. Michael Winston raced up and down the East Coast and across the Atlantic. (Photo By Larry Bulman)
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By Joe Holley
Washington Post Staff Writer
Wednesday, February 13, 2008

J. Michael Winston, 71, was a retired mortgage banker who died Jan. 30 of cancer at his home in Haymarket. He was a lifelong resident of Georgetown until moving to Haymarket last year.

Mr. Winston was indeed a retired banker, but the description is about as accurate as describing Wilbur Wright as a bicycle mechanic.

He was a dedicated bon vivant who, while still in his 40s, happily exchanged his banker's pinstripe suit and Windsor-knotted tie for a sailor's foul-weather jacket with a message across the back that read, "Pick Me Up First." A yachtsman and sailor for more than 30 years, he took part in dozens of races along the Eastern Seaboard and across the Atlantic.

When the man his yachting buddies called "the Silver Surfer" wasn't sailing, he was sharing adventures with filmmaker Robert Perkins and providing financial support for documentaries set in Mozambique, the Canadian Arctic and other exotic locales. He also was a serious fly fisherman and an avid tennis player who won several club championships.

He collected antique cars, including a 1959 Cadillac Fleetwood, a 1964 Pontiac GTO and a 1959 Bentley. At one time he was the proud owner of 11 Turbo Spider Corvairs, the early rear-engine compact from General Motors.

Mr. Winston was born in the District and graduated in 1958 from Washington and Lee University, where he was a member of Sigma Chi fraternity. He served in the Marines from 1964 to 1966 and then joined his father's mortgage banking and commercial real estate firm, the Carey Winston Co., now Transwestern. He became president of the company and also served as president of the Mortgage Bankers Association. He retired in 1986.

"He was very clubby," said Larry Bulman, a Chevy Chase attorney who sailed with Mr. Winston for more than three decades. Mr. Winston was a member of Chevy Chase Country Club, the Metropolitan Club, the Georgetown Club, the Gibson Island Club, the St. Francis Yacht Club and the Naval Academy Sailing Squadron.

He was co-owner with Bulman of a 38-foot racing yacht called the Yellow Jacket and later a 40-ton, 77-footer called the Javelin. The two friends competed in the biennial Annapolis-Newport race, the Governor's Cup Yacht Race and numerous other races on the Chesapeake Bay.

Mr. Winston's passion was offshore racing. He competed in the Southern Ocean Racing Circuit, racing from Fort Lauderdale, Fla., to Key West, Fla., and Montego Bay, Jamaica; Marblehead, Mass., to Halifax, Nova Scotia; Newport, R.I., to Bermuda; and other routes. In May 2005, he competed in the Trans-Atlantic Rolex Race from New York to England aboard the Staad Amsterdam, crewed by the Storm Trysail Club.

"He was a good helmsman," Bulman said. "You'd have a lot of fun with him and a lot of laughs, but he took his sailing fairly seriously."

Skipper Bulman's only complaint was that his veteran crew member could be hard to locate when night watch duty rolled around. Chances are he would be laid out in his bunk, stowed away in a life raft or tucked into a sail bin.

Eventually, he'd wander up on deck wearing his trademark World War I aviator's cap and armed with his "joke of the day."

Tall and handsome, a former Washingtonian magazine "most eligible bachelor" who remained unattached until age 70, Mr. Winston inspired yarns about his romantic adventures. Among the repeatable was Bulman's recollection of his friend, a superb cook, fending off an amorous admirer while trying to boil a lobster in the galley after a race to Jamaica.

At Newport, Pebble Beach, Calif., and elsewhere during the social season, he frequently had offers to be a "gentleman walker" -- an escort for unattached women, young or old. "He was a safe date, someone you'd set your sister up with," said Lynn Moffat Winston, his companion of 12 years and wife of one.

"He was one of the most urbane people I've ever known," said Perkins, whose documentaries, made with Mr. Winston's financial backing, have appeared on PBS and in England. Perkins recalled paddling down a river for 72 days in Canada's Northwest Territory with the assurance that at the end of the journey, "Michael would meet me right there and have a lovely bottle of wine."

Mr. Winston also volunteered in the emergency room of Georgetown Hospital and participated in Big Brothers Big Sisters. A young man he mentored became a surrogate son.

Survivors include his wife, of Haymarket, who married him after he was diagnosed with cancer. "His motto was 'onward and upward,' " she said. "That's how we both dealt with it."

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