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The '21' Club's Havana Gamble

When ‘21’ was the place to be for cigar-loving celebrities, Sheldon Tannen cut a deal to keep the Cuban cigars flowing long after the embargo
| By Mervyn Rothstein | From Jon Voight, November/December 2015
The '21' Club's Havana Gamble
Preparing for a busy day at the ‘21’ Club’s popular Bar Room, which is festooned with “toys” from its famed clientele.

In 1931, Ernest Hemingway was caught in its kitchen having sex with gangster Legs Diamond's girlfriend. Holly Golightly dined there in Breakfast at Tiffany's, as did the book's author, Truman Capote. Grace Kelly had its food delivered to an incapacitated Jimmy Stewart in the movie Rear Window.

Frank Sinatra, Humphrey Bogart, Lauren Bacall and Elizabeth Taylor ate there, as did Groucho Marx, Jackie Gleason, Luciano Pavarotti, Audrey Hepburn, Helen Hayes, and Dorothy Parker, nearly a dozen American presidents and all kinds of business moguls. Its walk-in humidor—cigars were a major feature of the restaurant before the New York smoking ban—was home to the good smokes of Yul Brynner, Jack Lemmon and John F. Kennedy (when he was a senator) as well as Henry Ford II and the Duke of Windsor, among many others.

It's the ‘21' Club, and for several star-filled decades in the mid-20th century it was the Manhattan meeting place for celebrities from all over the world. Sheldon J. Tannen, who is a member of the founding family that owned ‘21'—and was part of the management team that conceived its cigar company as well as a hotel and restaurant management company—knew them all. In his youth, Tannen was responsible for a major cigar coup, and because of him, nearly one million Havana cigars made their way to the restaurant's hands after Fidel Castro took over in Cuba but before the United States declared an embargo.

Tannen, who is writing a book on his ‘21' days, started in 1947 as an apprentice, left to work for his father, Henry, and Bill Hardy at Bill's Gay Nineties and returned for good the next year as assistant to the chief steward. When he left in 1988, he was chairman and president. As he turns 91 this year, he still maintains a small office in the lobby of the apartment building where he lives just off Fifth Avenue on Manhattan's Upper East Side. He's thin and fit, and looks younger than his age.

What attracted the stars, captains of industry and the power elite to the tables at ‘21'? "There was a feeling of welcome to those people who had come across our front door," Tannen explains. "My Uncle Jack was a great host," he says, referring to Jack Kriendler, his mother's brother, who cofounded ‘21' in 1930 with Charlie Berns, a cousin. For many years, the midtown Manhattan eatery and bar was known as Jack and Charlie's 21, and many of the cigars from the restaurant's heyday bear that logo.

Uncle Jack, says Tannen, "believed in treating every customer who came in to ‘21' as a very special person. Everyone was known by their full name, and they were treated as if they were the chairmen of the board of their domain—as they were."

Tannen tells the tale of how ‘21' became a celebrity hangout, a story that began far from New York. His uncle Jack, "a devotee of the Wild West," traveled to Palm Springs, California in the 1920s and 1930s, at the beginning of the formation of the Racquet Club, which was founded by actors Ralph Bellamy and Charles Farrell, who were Kriendler's friends. "It became an oasis for the celebrity crowd of Palm Springs," Tannen says. "They attracted every movie star and every big shot imaginable."

"Jack was a kid from Stuyvesant High School [an elite Manhattan public high school] and very bright, and had been a shoe salesman," Tannen explains. "His father had died of the flu in the epidemic [of 1918]. His mother had eight children, and the family were left to fend for themselves. My grandmother was the midwife of the Lower East Side. She delivered over 3,000 children, and she supported the family. But Jack, who was the oldest child, wanted to do something more creative. Wanted to express himself.

"An uncle, Samuel Brenner, who was a restaurateur and saloonkeeper from Europe, was Jack's inspiration. He was a leader among men. He was always very well dressed, and taught Jack the finer things of life, and Jack wanted to emulate him."

That emulation led to the saloon business, and before it was a restaurant, ‘21' was a speakeasy. Its origins go back to 1922, when Kriendler and Berns opened an on-the-sly drinking spot in Greenwich Village known as The Red Head. "Jack was 22 years old at the time," says Tannen, "and he and Charlie Berns decided, ‘This is where we can make some money.' They started in Greenwich Village, catering to college kids, but always right from the beginning serving the real McCoy. If you came into their place, after your first visit you knew this is where you were going to get Scotch that was Scotch, gin that was not bathtub gin, and you were going to be looked after well and want to come back."

A year later they moved to another location in the Village under the name Club Fronton. In those early years its patrons included Mayor James J. Walker and poet Edna St. Vincent Millay. Kriendler and Berns moved in 1926 to 42 West 49th Street and opened The Puncheon, and then, when that building was going to be torn down to make way for Rockefeller Center, they found a home at 21 West 52nd Street. On New Year's Eve, 1929, the restaurant opened its doors, and ‘21' was officially born.

21 Club
Photo/Jeff Harris
The ‘21’ Club was a cigar lovers’ sanctuary, and it had its own private-label cigars made in Cuba.

The club was often raided, but Feds hunting for illicit hooch found nothing, even after one search that lasted five hours. The owners of ‘21' not only had revolving bars, hidden chutes and other means of deception, but their pièce de résistance was a secret hideaway for their stash designed by architect Frank Buchanon.

Behind a 2.5 ton hidden door built into one of the kitchen's many archways—accessible only with an 18-inch-long metal skewer, which also served as a key when inserted just so into a crack in what looked like a solid wall—was the ‘21' Club's wine cellar, which housed the illegal wine and spirits. The room was actually not on the property at all, but the basement of the neighboring building. The room, which held 2,000 cases of wine, is still in use today, but its illicit days are over, and it now serves as a private dining room seating 22.

Wine at ‘21' was always a big deal. Among the 2,000 cases of wine it sheltered, the restaurant says, were the selections of Presidents Richard Nixon and Gerald Ford, Mae West, Eva Gabor and Aristotle Onassis. The wine list at ‘21' remains top-notch today, as the restaurant holds a Grand Award from our sister publication Wine Spectator, the magazine's highest accolade.

In addition to fine service, ‘21' has long had a unique look. Yesterday and today, the restaurant stands out for its special décor. Outside are small statues of jockeys, more than 30 of them, which trace their lineage to one donated in the early 1930s by regular patron Jay van Urk, according to the restaurant's website. That sparked donations of similar statues from wealthy racing patrons—from such families as Vanderbilt, Mellon and Ogden Mills Phipps—each one painted with its family's racing colors. "If their horse won the Kentucky Derby, Preakness, Belmont Stakes or Breeders' Cup," says Tannen, "their jockey was put in the place of honor atop the stairs."

Inside, hanging from the ceiling in the Bar Room, are toys and souvenirs donated by well-known diners. The first, a model of the British Airways "flying boat," dates from 1931. There's also a baseball bat from Willie Mays, a tennis racquet from John McEnroe, a golf club from Jack Nicklaus, a model of Air Force One from President Bill Clinton and a PT-109 boat from President John F. Kennedy. (The two were hardly alone in their presidential dining; the restaurant says every president since Franklin D. Roosevelt, except for George W. Bush, has been a patron.)

While wine was important to '21,' and remains so to this day, cigars were an equal part of the draw, and patrons puffed away heartily before, during and after meals. "They came for the whole experience, which included their cigars," says Tannen. "Our cigars were the best that could be purchased."

The cigars were stored in an attentive way, and in a very special spot. A year or so after Jack Kriendler died in 1947, his small office was turned into a walk-in humidor, with "shelving on a six-foot-tall by three-foot-wide revolving bookcase," Tannen wrote in his book, which "exposed all cigar boxes to air and humidity with the movement of a wrist. It was there we kept supplies for counter cigar sales, and began storing customers' private reserves for their after-dining availability. We showed our smoking customers this new humidor, and didn't have to ‘sell' them on keeping cigars there. They requested it. As a result of that small expansion, a cigar smoker could stop by the cigar counter on arrival, smoke the cigar after dinner, and if he liked it, stop by the counter and ask to take a box home, send a box to his office, and/or keep a box in our humidor."

By 1958, the restaurant's Cuban cigar sales were booming. Tannen says they had reached a heady $1.25 million, worth more than $10 million in 2015 dollars. But in 1959, Fidel Castro overthrew the military dictatorship of Fulgencio Batista. Tannen became worried about the future of ‘21's cigar supply.

"While everyone was saying [Castro] was a lot of talk and no action, I said, one of these days there's going to be action, because this guy's talking out of both sides of his mouth," Tannen says. "He's talking democracy and he's also talking socialism. ‘Everyone will be equal in our country and we will make industry recognize that.' All of his rhetoric was socialistic and anti-American. But he was our friend, he was our ally, he had lived in the United States. We thought he was still our ally."

In 1959, the biggest importer of Cuban cigars in the United States was Faber, Coe & Gregg. It was the source of all of the ‘21' Club's Cuban cigars. "I had spoken to [president] Donald Gregg, and told him, ‘What are we doing about it? We're going to need cigars." Tannen was worried about a decline in quality, and the possibility of a Castro nationalization. "I said to him, ‘We're not going to have enough cigars to take care of our patrons.' "

According to Tannen, Gregg didn't think there would be a problem, but Tannen did. So he went to his uncles at ‘21.'

"I had a terrible argument with my uncles about it," he says. "They said, ‘Can it. Forget it.' " But one uncle—Maxwell A. Kriendler, or Mac, as he was known, agreed, and persuaded the others. Soon, Tannen and his Uncle Mac were off to Cuba to buy cigars.

On the Monday before Memorial Day they flew on a 9:30 a.m. PanAm flight from New York to Miami, where they caught a connecting flight to Havana. The following day, they were driven from Cuba's capital city to the western province of Pinar del Río. They had lunch at the Por Larrañaga plantation, and placed an order. "I picked out the sizes and shapes, which they had on record," Tannen wrote, "and the particular leaf of tobacco for the wrappers." Tannen and Mac went to each major cigar factory in Havana to complete their shopping.

The cigars they bought—close to one million cigars, thousands upon thousands of boxes—were shipped from Havana in the fall of 1959. Many of the cigars cost 30 cents apiece, while others were 35 cents. The charge to ‘21' was a little more than $250,000, and when adding importation fees, duties and taxes, the total price, says Tannen, was around $275,000. The cigars arrived on schedule, and went into the cellar of the warehouse at ‘21.'

In September 1960, Castro nationalized Cuba's cigar industry, seizing cigar factories and the country's greatest brands. In 1962, President John F. Kennedy signed an embargo on Cuba, closing the door on Cuban cigars in the United States with a ban that continues to this day. But ‘21' had cigars for its patrons, and an advantage over other top restaurants. (The embargo was declared by President Kennedy, a Cuban cigar lover himself, who just before the announcement had his press secretary, Pierre Salinger, go out and buy 1,200 Havanas.)

The ‘21' Club not only had enough Cubans for its diners, but for other restaurants and customers as well. "As soon as the nationalization started, within two weeks I got a call from Hernando Courtright," a part owner and manager of the Beverly Hills Hotel, "the place to go if you were in Los Angeles, and he said, ‘Sheldon, I can't get any decent cigars out here. What are you guys doing to protect yourselves?' And I said we had taken steps to protect our future." Courtright told Tannen he could use "a couple of thousand of assorted cigars." Tannen said he would call him right back.

"I went upstairs and met with my uncles after lunch and said I had a call from Hernando. We still had the shipment sitting in our warehouse in reserve. And they were aging under good conditions—cellar conditions, which are where you want your wine and tobacco to be stored. Damp and cool....and I said let's think about going into the wholesale cigar business. I said now that there is nationalization, our government must put an embargo. Things have changed." And ‘21' began making private-label cigars, with 100 percent pre-embargo Cuban tobacco.

"When our new company, ‘21' Club Selected Items Limited,' was formed," Tannen wrote, "I became an equal partner and president."

The business was a good one, but ‘21' remained focused on its core. "We never gave a discount to anybody. Our cigars were by the cigar, times 25—that's the box. We were not a retailer. We were just a convenient place to have a good cigar. We wanted people to have an experience."

On December 31, 1984, the Kriendler, Berns and Tannen families sold ‘21' to investors Marshall Cogan and Stephen Swid. The sum was in the neighborhood of $21 million, according to Tannen. He became chairman and president of ‘21' Club Inc. until he departed in 1988.

Today, the cigars are gone at ‘21,' removed after New York restaurants went smoke free. Some of the cigars live on in the humidors of collectors. More than 30 years after the sale, Tannen continues to learn new things about ‘21.'

Take, for instance, Humphrey Bogart. In Casablanca, when Victor Laszlo (Paul Henreid) and his wife, Ilsa (played by Ingrid Bergman), come into Rick's café, they ask for a table close to Sam, as in "Play it, Sam," but far from Major Strasser, the German officer who is in Casablanca to hinder them. Bogart's character Rick Blaine says to put them at table 30—a reference to the great actor's preferred table at ‘21.' Tannen himself didn't even notice at first. "I spotted it on the fifth or sixth—maybe the 20th time—I watched the movie."

"If he was in New York, he was in ‘21,' " Tannen says of Bogart. "Before we opened—he came at a quarter to 12 every day. He had his table—table 30." That's something about Bogart, Tannen says, that nobody else knows. "Nobody in the world but me." 

Mervyn Rothstein is a frequent contributor to Cigar Aficionado.