People have kidded Jack Kiffer that he’s made the front page of the Shelter Island Reporter more than anyone else in history. That can’t be true. Supervisors always get a lot of ink. But the irrepressible — some would say shameless — proprietor of the Dory restaurant and bar on Bridge Street since 2004 has hit the headlines a lot over his nine years there.
“Infamous” is the right term, said the 70-year-old Mr. Kiffer with a tired smile last week during a long, rambling chat at the Dory, where a small post-lunch bunch sat at the bar nursing their beers.
Perhaps he’s best known, at least among people who don’t really know him, for hauling a commode into Volunteer Park a few years ago and sitting on it with a newspaper in his hands and his pants down around his ankles. The point was to protest the lack of public toilets on Bridge Street.
“All publicity is good publicity,” Mr. Kiffer said of the episode.
So who is this familiar Island character? He was born in Rockville Center in 1942. His mother worked at the Grumman plant in Bethpage, riveting Hellcats together, and his father was a mechanic with the Army Air Corps serving in Europe and Africa during World War II.
Mr. Kiffer and his mother lived with his grandparents during the war. “I thought they were my parents,” Mr. Kiffer said. Three-and-a-half years old when the knock came at the door, he remembers seeing a man in uniform standing there. “I didn’t know who he was,” said Mr. Kiffer. “I became extremely jealous. I didn’t like him from that moment. I was the crown prince. Actually, I was spoiled rotten.”
He never got along well with his dad, who drove a milk truck after the war and eventually started a contracting business. Many years later, he would base it in East Hampton and build a house in West Neck on Shelter Island. By then, Jack had planted his own roots here.
The oldest of four boys, he was a member of Syosset High School’s first graduating class of 1960 and well known as a “troublemaker and a kidder,” he said. “I was always getting into mischievous trouble, cutting school, playing practical jokes.”
He went to college at Farmingdale to study aeronautics, having been bitten by the flying bug when his uncle feigned engine trouble and landed his Army L19 two-seater in a Hauppauge field just to take Jack up for a ride. His next-in-line brother, Jim, now 66, got the bug too. He is a professional pilot who graduated from the U.S. Naval Academy and flew for Delta until early retirement. He’s with a charter outfit now in Florida. Jack didn’t stick with college but he did learn to fly at long-gone Zahns Airport in Amityville. Eventually, he bought his own plane, a four-seat Cessna 170B that he based here at Klenawicus airfield. He sold the plane after five or six years because he wasn’t using it much.
After quitting college, he bluffed his way into a job with a photo lab in Mineola that processed film for Madison Avenue. “I lied when I took the job. I told them I knew all about photography,” he said. In fact, “I didn’t know what I was talking about.”
He and a friend shared an apartment in Roslyn and became regulars at a joint called the Cabana in Bayville, where he hung out with friends and dated “a bar maid,” he said. He “had a great time” and “should have wound up in jail” because he and his pals were doing so many “crazy things,” he said.
“I had a motorcycle that I kept in the kitchen. They kept taking it away from me,” Jack said of his pals, “because I was so damn drunk. They’d take the distributor cap away.”
As much as Jack liked to have fun — and booze and barmaids were a big part of it, as he readily admits — something else was going on, something he doesn’t mention, much less gloat over or explain: call it entrepreneurial instinct.
In the early 1960s, as Long Island boomed with suburban sprawl, he started his own trucking company hauling sand and gravel. It hit the jackpot when a tugboat strike forced Con Edison to hire truckers to haul coal to its big Ravenswood power plant in Long Island City.
He was even more successful when he became a partner in a New York restaurant and gave up the trucking business. Soon he tried his hand at building restaurants for others. Mr. Kiffer offhandedly listed J.G. Mellon, Ben Benson’s steakhouse and the Hudson River Café among the places Kiffer Contracting of Woodbury and later Farmingdale built for clients over two decades in Manhattan, Brooklyn and Long Island.
The pivotal moment in Mr. Kiffer’s career came when his Roslyn roommate got a job at a bar in the city called Geordie’s and Jack went with him to live in Manhattan. “I wound up hanging out at a place called Don Denton’s and I became a partner,” Jack said offhandedly. Pressed, he said only, “Don was always in financial trouble. I had some money. I funded the place. We became partners.” The money came from the trucking business.
Another hot spot on the city’s preppy bar scene was “the very successful” restaurant and bar called Edwards on 61st and Lexington, Mr. Kiffer said. Through his partying and his work in the business, Mr. Kiffer became fast friends with its proprietor, who was about eight years older than Jack but “as crazy as everybody else on the block.”
Dick Edwards, whose father was president of U.S. Steel, Mr. Kiffer said, introduced him to Shelter Island and raucous weekends at the Edwards estate in Dering Harbor and at the Dory, then owned by Mal Nevel. Jack soon started to rent houses on the Island, which he’s still doing.
“I’m a drifter,” he said, “living just short of a shopping basket. What can I do?”
He does have an apartment in the city and he did own a house for a while in Noyac but that became a problem after Mr. Edwards left him the Dory and he had to sleep in his truck whenever he missed the last ferry.
Mr. Edwards had loaned Mal Nevel the money to buy the Dory back in the 1960s. When Mr. Neville decided he didn’t want it anymore, he let Dick Edwards have it for his last $1,300 mortgage payment, Mr. Kiffer said. “Dick kept it only because there was no one else to keep it going and he wanted a place to drink,” he explained.
When Mr. Edwards began losing a long fight with cancer, Mr. Kiffer helped keep the Dory going and helped care for Mr. Edwards. Three days before he died in 2002, he realized his brother Bob, to whom he’d left everything, wouldn’t know what to do with the Dory so he called in attorney Bill Sulahian to change his will, leaving it to Jack.
“I loved the Dory,” Mr. Kiffer said. “I was doing very well … I had a good reputation” in the restaurant business but “this place needed a massive amount of work. It was going to fall down,” he said. There was a hole in the floor near the bar “and somebody was going to get hurt.”
He gave his restaurant-building business to “a guy working for me” and dove in. The first winter after he refurbished the place, he stayed open all winter “and took my lickings like a man.” He didn’t try that again until last year, when pals in the Fire Department gave him a big dinner, made him an honorary fireman and “nailed me to the wall,” he chortled, by pleading with him to keep the bar open all year.
Mr. Kiffer, who quit drinking last July, has always had a long-term relationship with someone, he said. Dory regulars will remember a beauty named Milen, a waitress he met masterminding a grand wedding reception for hundreds of people on a cruise ship that was docked at 23rd Street. Milen served as his hostess and bartender for years. She’s back in the city now and Mr. Kiffer said they’re still friends.
He is looking forward to closing for just a while this winter, probably later this month, so he can take some time off. Maybe he’ll head to Costa Rica, where he owned some property for a time, or pay one of his regular visits to his brother in Florida.
“I’m here every morning,” he said. “I do the banking, the books, and I handle any problems that come up. That part doesn’t bother me — but I need some relaxation.”
“This will be my grand finale,” he said of his tenure as the Dory’s fifth owner since it was built in 1925. “I’ll fall over dead one day or sell it and go to Costa Rica.”