21 expanded underground before expanding on street level
To store all the booze, the club made a deal with the neighbors at 19 W. 52nd St., using their basement -- accessed by a hidden, two-ton door to which the only key to this day is an unsuspicious meat skewer -- to keep excessive amounts of booze. The club could very easily say there was no booze on the property, because it was all stored in #19. Eventually 21 bought 19 and then the next townhouse as well, and the restaurant you see today is a combination of the three buildings.
The mob had it in for 21
Legs Diamond, a famous mob boss at the time, wasn’t thrilled that 21 made alliances with the police department rather than with the mob (the other way to source booze during Prohibition). It’s said that Diamond put a hit out on Jack and Charlie and planned to come down to NYC from Albany to do it himself, but somebody took him out first.
Ernest Hemingway had sex there
When visiting 21, Hemingway would famously declare, “Since I’m not drinking, I’ll just have a tequila.” One night, when he was there for a dinner party, he met an attractive woman with whom he spent the remainder of the night talking and eating and drinking. When it was time for the restaurant to close for the night, Hemingway asked Jack (the owner), if they could stay for a while. Jack was known for saying yes to everything, and he agreed to let them linger while the restaurant cleaned up. “They got to know each other very, very well, intimately even, on our kitchen steps... they’re pretty darn steep!” Fletcher claims. Apparently, the next day Hemingway came back to the restaurant and said “Jack, I have a problem: what’s her name?” And as it turned out, he had romanced Legs Diamond’s girlfriend.