How Frank Sinatra’s favorite New York joint became a meeting place for Soviet-era dissidents

West 52nd Street between Broadway and 8th Ave. is today one of those anonymous New York City blocks that seems, at first glance, to offer very little other than the entrances to the Neil Simon and August Wilson theaters that dominate the street. Tucked beneath a nondescript red awning beneath the buzzing Neil Simon sign is a piano bar and restaurant called Russian Samovar. The entrance is plain. The awning promises a “House of Flavored Vodkas,” which for some drinkers, is not an enticement, conjuring as it does chilling images of whipped cream and birthday cake flavored shots of Smirnoff. The menu posted in the front window boasts an array of traditional Russian fare: caviar and blini, salmon kulebyaka, vareniki, tabaka, beef stroganoff, and of course chicken Kiev. A climate like Russia’s doesn’t inspire light and delicate fare.

Russian Samovar opened in 1986, a partnership between three Russian expatriates: literature professor Roman Kaplan, famed poet Joseph Brodsky, and legendary ballet dancer Mikhail Baryshnikov. All three men considered themselves “fundamentally pro-Russian, yet vehemently anti-Soviet Union.” They wanted a place where like-minded artists could gather, talk, listen to music, and eat. Though most of the world didn’t realize it at the time, the Soviet Union was only a few years from dissolution, the Berlin Wall — a chunk of which used to sit a few blocks away on 53rd Street between Fifth and Madison Avenue — just a couple years from being overwhelmed and sledgehammered by jubilant Germans. For many members of the Soviet diaspora who found themselves in New York City, Russian Samovar became a de facto home far away from home, where everything from politics to poetry was discussed over hearty dishes and glasses of vodka.

The Soviet Union is gone now; but Russian Samovar is still there.

Through the door, away from the crowd waiting to see Jersey Boys across the street, one is greeted by red boudoir lights, like something a saloon madame might have once worn, and on the right, a long wooden bar behind which is arranged, among other liquors, some fifteen different house-infused vodkas. The vodkas came in the 1980s but the wooden bar has been there since the 1960s, when the place was called Jilly’s Saloon after its owner, Italian-American entrepreneur Jilly Rizzo. Jilly’s was famous for a number of reasons, but two stand out above all others. One, someone decided there to murder Johnny Carson; and two, when Frank Sinatra was in New York, it’s where he would set up court, dining there several nights a week flanked by friends and associates while three waiters and Jilly himself ran interference on anyone hoping to drop by Frank’s booth without an invitation.

We’ll wind up at Jilly’s right after Toots Shor’s

Despite having served as an icon for high living for generations, Frank Sinatra was not a fan of haute cuisine. A high school drop-out from Hoboken, New Jersey, the only child of father who was a lightweight boxer turned fireman and a political activist mother who ran an illegal abortion business that provided services for free, Sinatra even after his fame was established preferred simpler fare and cozier surroundings than were found in the five-star restaurants of the world. In New York he favored only a few establishments, none of them popular celebrity hang-outs (except for the celebrities invited by Frank). There was P.J. Clarke’s at 915 Third Ave., where Sinatra carefully scheduled his nights around those of gossip columnist Dorothy Kilgallen, whose favorite topic was anything going wrong in Sinatra’s life, especially if it concerned the disillusion of his relationship with actress Ava Gardner.

Then there was Patsy’s at 236 W. 56th St., where Frank ordered the breaded veal and spaghetti with red sauce on the side. As a story goes, Sinatra found himself on the skids one Thanksgiving, without company and without plans. So he made a reservation at Patsy’s, which wasn’t open that day. But owner Pasquale Scognamillo scrambled his staff and family so that when Frank rolled in at 3pm, the place was full. Rocky Lee Chu-Cho Bianco at 987 Second Ave was where Frank would go for pizza, and if he wanted something a little more upscale, he hit the 21 Club over at 21 W. 52nd St., where the jacket and tie dress code was a lot less of an issue in the 1950s than it is now. But above and beyond them all was his affection for Jilly’s Saloon.

Born Ermenigildo Rizzo on May 6th, 1917, Jilly’s career in food services started early, when worked for his father delivering Italian ice to cafes. He opened his first restaurant, Jilly’s Saloon, on West 49th Street but eventually moved it to a new location on West 52nd. It was this second incarnation of Jilly’s that attracted Sinatra’s attention. On any given night, Sinatra could be found at his regular booth surrounded by regular friends who received the call earlier in the day — having grown up an only child, Sinatra swore he would never dine alone. Jilly’s kitchen specialized not in Italian fare but in Cantonese food. Sinatra spent so much time there that Jilly Rizzo became Sinatra’s closest friend, his right-hand man, and his bodyguard.

By 1962 he and Jilly Rizzo were so close that Sinatra was securing bit parts for the saloon owner in films like The Manchurian Candidate. That same year, Sinatra and fellow Rat Packer Sammy Davis Jr. recorded the duet “Me and My Shadow,” which twice mentions ending up at Jilly’s. In Sinatra’s 1968 detective movie Lady in Cement, he pays tribute to his friend by naming a seedy Miami strip club Jilly’s. also in 1968, Sinatra once again paid musical tribute to his favorite hang-out when, in the song “Star,” he crooned “If they’ve got a drink with her name in Jilly’s bar, the chances are the lady’s a star.”

Apart from being Sinatra’s throne room, Jilly’s was most famous as the spot where mobsters decided to murder television comedian Johnny Carson.

Russian Revolution

There’s still music at Russian Samovar, and Frank’s table is still there though few people out for the evening are aware of the role the spot once played in the life of the Chairman of the Board. Jilly’s wasn’t going to last forever, and as the inevitable procession of time faded the glory of the Rat Pack era, Jilly’s Saloon’s current manager, Tony DelVecchio, had to shut the place down. Jilly, who had served as the face of the bar he began, retired as well. The place ended up in the hands of Roman Kaplan, Joseph Brodsky, and Mikhail Baryshnikov. All three men were expatriates and exiles. Brodsky was born in 1940 in Leningrad, and while still a child he endured anti-Semitism, poverty, and the brutal siege of Leningrad during World War II. He was a rebellious child who developed at an early age a dislike for the omnipresent images of Lenin that peppered the Soviet Union. After dropping out school, he bounced through a series of jobs and, in 1955, started writing poetry for the underground journal Sintaksis. His fame spread through the underground rapidly, and for several years he enjoyed a great deal of acclaim and success.

As acclaim and success were wont to do during the increasingly paranoid later years of Stalin’s reign, they got Brodsky on the bad side of the government. He was denounced as a poor contributor to society, a pornographer, anti-Communist, and most outlandishly, “a pseudo-poet in velveteen trousers.” He was sentenced to five years of hard labor in the icy Arctic north, only 18 months of which he served before protests by prominent Soviet and foreign citizens secured his release. Contrary to the intentions of his rivals, Brodsky was rather fond of his time in the Arctic, enjoying the labor and the amount of time for quiet contemplation, reading, and writing his rustic isolation afforded him. After his return to Leningrad, he continued to write and continued to rub authorities the wrong way. In 1972, the Soviet government strongly suggested that Brodsky would be happier in Israel or, really, anywhere other than the USSR. Brodsky disagreed, stating flatly that he wanted to stay in Leningrad. Less than two weeks later, the government again suggested that he leave the country — this time by burglarizing his home, stealing all his papers, and forcibly placing him on a plane bound for Vienna. Shortly thereafter, having no interest in Israel or England, the exiled poet settled in the United States.

The same year Brodsky found himself being hustled onto a plane by KGB agents, his countryman Roman Kaplan was boarding a plane for Israel with no intention of coming back to the Soviet Union. In 1974, the most famous Soviet ballet dancer in the world, Mikhail Baryshnikov, defected while in Toronto. Kaplan, like Brodsky, was born in Leningrad around the same time (1938) and endured many of the same hardships during the war. He moved to Moscow and became a Professor of American English and Literature, but by the 1970s, he was ready to live somewhere less oppressive. Eventually, Kaplan found himself in New York, where his passion for Russian art led to a job in a gallery. His position there introduced him to many prominent people, many of them similarly exiled from their home, their culture, and their food. Inspired by this, Kaplan opened his first restaurant, Kalinka, in 1984. In 1986, he sold Kalinka and opened a new restaurant at 256 W 52nd St., the former home of Jilly’s.

His contacts in the art world brought two business partners into Russian Samovar. In 1986, Baryshnikov became a naturalized citizen of the United States and agreed to get involved with Russian Samovar. In 1987, Brodsky won the Nobel Prize in Literature and invested the earnings into his friend’s new restaurant. They all shared a vision of a friendly, open space that would encourage art and expression. Kaplan, having read about the process of infusing vodka with various flavors, introduced the first infused vodka bar in the restaurant, a trend that would be copied by many bars and restaurants and that shouldn’t be entirely blamed for the eventual proliferation of whipped cream and birthday cake flavored Smirnoff.

The Killer and the Comedian

There’s no record of what Tonight Show host Johnny Carson was drinking one night at Jilly’s in 1970 when inebriation got the better of his judgment and led to him flirting with a woman who’d caught his eye. According to Carson biographer Henry Bushkin, the popular funnyman was doing his best to convince the pretty young woman to leave with him. Unfortunately for Carson, that pretty young woman was already spoken for — by rather a jealous and humorless New York mobster. Enraged by Carson’s amorous attentions toward his girlfriend, the unnamed mobster and his crew roughed Carson up, even throwing him down a flight of stairs. It would have gotten even uglier had Jilly Rizzo himself not intervened and cooled the situation down. But level heads prevailed only briefly — long enough for Carson to limp away and discover, shortly thereafter, that all was not forgiven. The mobster, still fuming, decided the world would be better off without Johnny Carson. A hit was issued. Carson spent the next three days hunkered down in his room at the UN Plaza hotel, canceling multiple appearances and hoping things might simmer down.

They did eventually, but only after Carson cut a deal with crime boss and civil activist Joseph Colombo. Under the terms of his agreement with Columbo, Carson brokered a deal with NBC to cover an Italian-American Civil Rights League rally. Mafioso Columbo had recently formed the League as a way to protest the stereotyping of Italian-Americans as a bunch of mafiosos. The hit was called off, and Carson was free to resume his life as America’s most beloved variety show host. Joe Columbo, on the other hand, was less fortunate. He was gunned down in 1971 at the second and final Italian Unity Day rally in Columbus Circle.

The trigger man was a street hustler named Jerome Johnson, working presumably on orders from Vincenzo Aloi, right hand man of Colombo’s rival crime boss Joe Gallo. Colombo survived but was left completely paralyzed. He passed away in 1978 and was buried in Saint John Cemetery in Queens. Gallo was himself gunned down in 1972 while dining at Umberto’s Clam House (129 Mulberry St.). Coincidentally, Gallo, his family, and his crew had just come from seeing Sinatra’s favorite comedian, Don Rickles, at the Copacabana on the West Side — a club made famous by Sinatra when he threatened to boycott the entire place over their treatment of black performers (Sinatra’s Summit pal Sammy Davis Jr. had been allowed to perform at the Copa — but not walk in through the front door).

A Taste of Russia, The Toast of Tennessee

Infused vodkas may be easy to find these days, but back in 1986 when Roman Kaplan got the idea from old Russian texts it was still new. Originally fabled to be aphrodisiacs (isn’t everything), Kaplan and his bartenders encourage drinkers to drink their vodka the traditional way — with a compliment of pickles. Samovar partner Joseph Brodsky passed away in 1996 of a heart attack. he was 55, and Kaplan still mourns the passing of his friend, one of the most famous poets to ever come from the Soviet Union. Though the restaurant has been around for decades now, Roman Kaplan still eats at Russian Samovar regularly. Gregarious, and welcoming, with a wizened, jolly face lined by a fringe of well-groomed facial hair, he’s no hands-off owner. He’s there almost every night, and if you want to talk about the history of the place, he’ll make time over the sounds of diners and live music. It might not be Sinatra, but the music is lively and, like everything at Russian Samovar, a reflection of the restaurant’s commitment to Russian arts. Kaplan is well versed in the history of Jilly’s and the booth Sinatra once used when he held court.

Jilly Rizzo himself, retired but still living the sort of life that led to things like a 1991 conviction for fraud (for which he was sentenced to 1000 hours of community service), was killed on May 6, 1992 — his 75th birthday — when his car was struck by a drunk driver in Rancho Mirage, California. Sinatra passed away in 1998. As befits the Chairman of the Board, he was the last one out the door. While vodka may be the star attraction at Russian Samovar, if you want to raise a glass to Sinatra, or enjoy hearty heaps of Russian cuisine in his favorite booth, they have you covered. His “gasoline” of choice all those years was bourbon — four ice cubes, two fingers of Jack Daniels, and a splash of water. And if you’re the type to “well actually” Sinatra about Daniels — he never called it “Jack” — being Tennessee whiskey and not bourbon, well I bet you’d soon be acquainted with the sidewalk outside Jilly’s Saloon and a gruff warning from Rizzo that it would be in your best interest not to come back.

This article was originally written in June, 2015, for Alcohol Professor and has been reprinted here with permission.

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