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1871-72:   Construction of the townhouse at 21 West 52nd Street gets underway. '21', as well as buildings 19 and 17 were part of a row of brownstones designed by the firm of Duggins and Crossman.

January 17, 1920: The Eighteenth Amendment goes into effect beginning the Prohibition Era.

1922:  To earn night school tuition, cousins Jack Kriendler and Charlie Berns open their first speakeasy, The Red Head, in NYC’s Greenwich Village. They attract the collegiate crowd. At the time, Jack is a pharmacy student at Fordham; Charlie's at NYU’s School of Commerce (he finishes his degree). Future journalist/screenwriter/producer Mark Hellinger is their cashier. 

1923: Jack and Charlie open Club Fronton at 88 Washington Place. Among the Fronton’s notable patrons: NYC Mayor James J. Walker and poet Edna St. Vincent Millay.

1926: Jack and Charlie move the business uptown to 42 West 49^th Street because condemnation proceedings start to make way for a subway around Washington Place. They name their new bistro The Puncheon, but (partly to confuse the federal tax men) it is also known as The Puncheon Grotto, Grotto, 42, 42 Club, Jack and Charlie’s, and Keyburn Club (its name when raided).

1928: Rockefeller Center is planned, and Jack and Charlie receive $11,000 from landowner Columbia University to vacate #42. They purchase a house on West 52^nd Street, and spend the next year converting it into a speakeasy and restaurant. 

December 31, 1929 - January 1, 1930: With the help of their patrons, Jack and Charlie unhinge the wrought iron gate that had been the portal to #42, and install it three blocks north at 21 West 52^nd Street. They open Jack and Charlie’s '21' Club in the wee hours.

1930: Daily Mirror gossip columnist Walter Winchell (the inspiration for Sweet Smell of Success character J.J. Hunsecker) is banned from ‘21’. As retribution, he runs a column noting that ‘21’ had never been raided by Prohibition agents. The next day, ’21’ is raided. Soon thereafter, Jack and Charlie hire architect Frank Buchanan to install a complex system to hide and destroy liquor in case of future raids, including the infamous ‘21’ Wine Cellar, now considered one of the world’s most coveted private dining rooms.

52^nd Street between Fifth and Sixth Avenues is nicknamed "Swing Street" and is home to over 30 speakeasies.

1931: A model of the British Airways "flying boat" is the first corporate toy hung from the '21' ceiling. Today, hundreds of corporate logo toys, sports memorabilia and other mementos form a ceiling-scape, including a model of the PT-109 donated by President John F. Kennedy, a smashed tennis racquet from John McEnroe, Jackie Gleason’s pool cue from The Hustler, and mics from every NYC-based television and radio station.

Jack purchases 19 West 52^nd Street; in 1935, its lower floor becomes an addition to '21'. 

1932: '21' is raided again in June when ten federal agents knock on the door. Doorman Jimmie Coslove squints through the peephole and, seeing the officers, activates a secret alarm that alerts management that a raid is imminent. The officers then burst in, and ransack the building, looking for liquor. After hours of searching the premises - closets, rooms, attic, basement - agents admit defeat and leave without finding the two thousand cases of contraband that is hidden downstairs. 

The great mystery as to why the agents never found the liquor? '21's secret Wine Cellar, built to be invisible. Behind several smoked hams (in the Wine Cellar) that hung from the basement ceiling and a wall filled with shelves of canned goods, stood a perfectly camouflaged two-and-one-half ton door that appeared to be part of the wall. Only opened by inserting a slender 18" length of wire through one of the many cracks in the cement wall, would the secret door silently slide back to reveal '21's most coveted treasure: two thousand cases of wine.

As a matter of record, '21's wine cellar was, and still is, in 19 West 52nd Street. When first opened, Jack and Charlie did not own the building at 19 West 52nd Street, they just borrowed the cellar. Because of this, when employees were asked by the feds if there was liquor on the premises, they could truthfully answer "No, sir!"

Another '21' legend: during Prohibition, New York City Mayor Jimmy Walker had a private booth in a corner of the cellar, where he would go to have a cocktail in peace as the feds were raiding the premises above for contraband. Mayor Walker's booth has been preserved, and can be viewed today by diners who can enjoy a seven-course tasting menu served with the finest wines under decidedly more favorable circumstances. 

December 5, 1933: Prohibition is repealed.