Sammy Davis did not need the work. By 1957, he was a big star. He had already twice performed as a headliner at the Copa, with fabulous success. He filled the club both times. He agreed to fill in for Sinatra and do the late show. Podell was highly appreciative. He arranged for Sammy and a group of ten friends to have ringside tables throughout Sinatra’s two-week run, all of it—food, drink, the tables—on the house.

  Sammy and Podell had a history. Podell was a brute of a man, known for his foul mouth and often equally foul disposition. He had a deep, raspy voice, a big head, and the physique of an aging longshoreman. He berated workers at the club and also the entertainers if he felt he had a reason. He wore a large star-sapphire ring on his pinkie finger, and when he wanted something from the staff or an employee, he would loudly bang his ring on a tabletop. It was a sound that instilled fear among the staff.

  If patrons at the club approached Podell, he might tell the person, “Get the fuck away from me, asshole.” He was so disagreeable that an FBI informant once told his handler, who memorialized it in a memo, that a group of mafia bosses once met to discuss replacing Podell at the Copa because he was believed to be bad for business.

  It had taken Podell a while to warm up to Sammy Davis Jr., even though the song-and-dance man filled the club from the first time he appeared there (in 1954). Once, when Sammy’s set ran long, which was a no-no at the club (Podell ran a tight ship), Podell banged his ring on a table and bellowed, “Get off my stage, nigger.”

  The night Davis was in the club to fill in for Sinatra, he came early with a group of friends to support Jerry Lewis. His entire group heard someone behind them complain about “that little nigger in front of me.” When a waiter and maître d’ could not silence the man, a captain came over to speak with the customer. “It’s obviously some kind of mistake,” said the patron. “I came here thinking I’m spending my money in a first-class place, so you can understand my surprise when I find my wife and I seated behind this little jigaboo.”

  The customer and his wife were immediately escorted from the premises.

  Rumors circulated that the National Association for the Advancement of Colored People (NAACP) was going to picket the Copacabana. Previously, the organization had picketed and boycotted the Stork Club, a rival of the Copacabana, for its treatment of renowned international entertainer Josephine Baker. The subsequent protest had been a nightmare for the Stork Club, leading to bomb threats and reams of bad press.

  Jules Podell may have been a racist, but he recognized that a boycott by the NAACP could lead to Black entertainers such as Ella Fitzgerald, Johnny Mathis, Nat King Cole, or even Sammy Davis turning against the club.

  Davis arranged for leaders of the NAACP to meet with Podell. Quietly, with no fanfare or press announcement, the Copacabana, in mid-1957, agreed to do away with its no-Blacks-allowed door policy.

  Even so, rightly or wrongly, the club retained its reputation as a segregationist establishment. Black entertainers were treated well at the club, but Black patrons did not feel welcome. Partly, this had to do with the club’s reputation as a “mafia joint.”

  The relationship between jazz and the underworld had come a long way since the days in New Orleans when Sicilians and Blacks first established working relationships that were at the heart of the jazz business. Somewhere along the line, the plantation mentality, which became an operating as well as aesthetic principle in the presentation of jazz, had come to dominate the relationship. Mob-run clubs, or clubs that were perceived to be “mafia friendly,” were likely to be the most backward when it came to treating Black people as human beings of equal stature with whites. Few people offered the opinion anymore that mob-controlled clubs were somehow especially good for Black jazz musicians. With their racist door policies and atmosphere of bigotry inside the club, those clubs were more likely viewed as an impediment to social advancement, not only in the nightclub business, but in society at large.

  Mambo Italiano

  Black musicians weren’t the only ones chafing under mafia rule in the music business. From nearly the beginnings of jazz history, Italian American musicians sometimes found themselves in a unique predicament. This was especially true for the singers.

  Frank Sinatra wasn’t the only one who seemed to capture the imagination of his tribe and then move on to conquer the larger population. Singers whose popularity in the marketplace elevated them beyond the tribe became sources of great envy and pride. Just as the Irish might have worshipped those among them who rose in the world of politics, or Jews took special pride in those who achieved great things in literature and academia, the popular Italian American singer represented the height of achievement to many, including the mobsters. Writes John Gennari in Flavor and Soul:

  From the 1940s to the 1960s, while many second-generation Italian Americans realized their dream in the security of owning automobiles and homes, Italian American popular singers (Sinatra, Perry Como, Dean Martin, Tony Bennett, Mario Lanza, Vic Damone, Jerry Vale, Joni James, Connie Francis, Bobby Darin) virtually defined the way America dreamed about love and romance.

  For the singers themselves, this often involved walking a tightrope between independence and fealty to the dictates of the mob. Pressure came from the business side of things—the nightclubs and talent management—but it could also come from the neighborhood.

  Vic Damone, born Vito Rocco Farinola in Brooklyn, described in his memoir an incident so “delicate” that he felt the need to use false names, even though the events of the story happened fifty years earlier. As a young man in his early twenties, Damone met and fell for the daughter of a mafioso he refers to as Johnny D’Angelo. At the time, in the late 1940s, Damone was already a professional singer with a rising career. He was ready to marry D’Angelo’s daughter, until one day he took his fiancée to meet his mother at her home in Bay Ridge. The two women got into an argument, with the fiancée calling Damone’s mother a bitch.

  “You called my mother a bitch?” said Damone. “Apologize right now or the marriage is off.”

  Johnny D’Angelo’s daughter was stubborn; she refused to apologize. Damone called off the marriage.

  D’Angelo the elder was livid. He lured the young singer to the Edison Hotel in Manhattan, under the pretense that they would discuss the matter. When Damone arrived, D’Angelo grabbed him and tried to throw him out the window. Damone was saved by his manager, whom he had brought along to serve as his bodyguard.

  In the wake of this incident, a major sit-down among the mafia bosses was arranged. The meeting took place at Hotel Fourteen, a boutique hotel that was part of the same building that housed the Copacabana nightclub. The hotel was owned by the owners of the club and used sometimes as a residence for performers from out of town, or for trysts, or sometimes for highly secretive mob sit-downs.

  Damone arrived at Hotel Fourteen, along with his manager. He was met by a bevy of important gangsters, along with Johnny D’Angelo. According to Damone, D’Angelo was seeking authorization to have Damone killed for having insulted his family name by calling off the wedding with his daughter.

  Inside one of the rooms in the hotel above the Copa, the mobsters debated the singer’s fate. Presiding over the meeting was Frank Costello, known in the press at the time as “Prime Minister of the Underworld” for his ability to broker settlements among various mob factions. Damone gave his side of the story about how D’Angelo’s daughter had besmirched his mother’s honor.

  Much to the singer’s relief, Costello sided with him and gave a thumbs-up sign, which meant Damone could not be killed.

  Damone was appreciative, but now he was indebted to the mob. When they called on him to perform at wedding receptions, baptism parties, first Communions, or whatever, he had to accept. Even if he had a previous booking, he was expected to cancel and make other arrangements, because from now on, he was part of the family.

  Tony Bennett, born Anthony Dominick Benedetto in Astoria, Queens, became a singer in the years following his time in the U.S. Army, where he experienced brutal combat in Germany and took part in the liberation of a Nazi concentration camp.

  Upon his return stateside in the mid-1940s, Bennett began to explore the possibilities of becoming what he called a saloon singer. He performed under the name Joe Bari. Singer Pearl Bailey heard the young singer one night at the Greenwich Village Inn, and she sought to help him out. Bari changed his name to Tony Bennett and, in 1944, signed a deal with Columbia Records.

  Bennett became frustrated with the slow pace of his development, so he took on a new manager. Ray Muscarella was a wiseguy who had also helped Vic Damone get started. Bennett knew of Muscarella’s mob connections; he had misgivings, but it seemed like the only way to go. Said Bennett:

  I felt I couldn’t pass up on the chance to get the good gigs I was sure Ray could get. I’d been scuffling long enough, on ten cents a day, and I couldn’t turn down any kind of help . . . [Ray] ran a few businesses in Brooklyn, his family owned a winery in Little Italy, he managed prize-fighters and he dabbled in show business. In those days, there wasn’t a business that wasn’t connected, one way or another, with the underworld. They owned the nightclubs. And ruled the jukebox business, then started up record companies to make records for those jukeboxes and signed up singers to make records, so they controlled it all. And it was understood by everybody that if you really wanted to make it, sooner or later, you’d run into one of those guys.

  In 1951, the weekly scandal magazine Confidential published a series titled “The Mob Moves in on Show Business.” In an adjoining article titled “Gangster Ghouls,” the magazine noted that “a character named Ray Muscarella, singer Tony Bennett’s manager,” had used his muscle to get Bennett’s record into eighteen thousand jukeboxes simultaneously. “The jukeboxes involved, for the most part, are owned and/or operated by the mob.”

  Muscarella was angry about the article. Together with an associate, he stormed the offices of Confidential and confronted the editor. The rumor was that they hung the editor outside a window by his ankles. To the mobsters, the editor concurred that he had made a terrible mistake. “From now on, I’m gonna read every article we publish,” he said. The following issue of Confidential included a retraction that appeared under the headline “When we make a mistake, it’s a beaut.”

  In 1960, Bennett came to the conclusion that his mobster/manager was more trouble than he was worth. The singer had never been comfortable with the arrangement. He suggested a buyout, but Muscarella was not interested. The situation became tense, until Bennett, for a fee of $600,000 and a 10 percent cut of his income for the next five years, was able to secure a release from Muscarella. Even then, he remained concerned that the mob would never stop believing they owned a piece of his career. The crooner never felt completely relaxed until after Muscarella died of natural causes in 1965.

  Singer Bobby Darin, born Walden Robert Cassotto in East Harlem and raised in the Bronx, was practically mob royalty. His maternal grandfather was Severino Antonio “Big Sam Curly” Cassotto, an Italian-born mobster who died in prison from pneumonia a year before Darin was born. Darin’s father was believed to have been in business with Frank Costello. Darin hardly knew his father, who died young. Precociously talented as a singer and performer at a young age, Darin was raised by his grandmother and led to believe that his real mother was actually his sister.

  When Darin first headlined at the Copacabana, at age twenty-four, he was told by Jules Podell, “If you want to know about your father, I know people who can tell you the whole story.” The implication was that the father was “connected.” The young singer wisely kept his distance from the mobsters, but they viewed Darin as “a friend of the family,” which led to his early booking at the Copa.

  The date was June 12, 1960, and the performance was recorded as an album, Darin at the Copa. Both the live appearance and the album were a sensation, and from then on the singer was identified with the club where every performer hoped to get a booking. Darin appeared there six times before his death from a lifelong heart condition in 1973. He was thirty-seven years old.

  Darin’s penultimate appearance at the Copa was the one that brought him into direct conflict with Podell and the mob. Starting in the late 1960s, Darin had begun to come under the influence of the counterculture movement and, particularly, early Bob Dylan. Up until then he had been presenting himself as the last of the great “ring-a-ding-ding”–type singers: always in suit and tie or sometimes even a tuxedo. His jaunty delivery and expert jazz phrasings were in the tradition not only of the great Italian American crooners but also jazz vocalists from Bessie Smith to Billy Eckstine.

  But now, Darin started to appear onstage in denim trousers and a jean jacket. He performed without the hairpiece he had been wearing since his midtwenties. And his performance repertoire changed. No longer the finger-snapping dynamo who assumed his role as successor to all the great saloon singers, he appeared onstage with a guitar and sang mostly folk-rock songs. No more “Mack the Knife,” “Beyond the Sea,” and other songs that were cherished by mafiosi from coast to coast. Now it was “Blowin’ in the Wind,” “If I Were a Carpenter,” and a song he wrote called “Simple Song of Freedom”—gentle protest songs that seemed to hearken the passing from one generation to the next.

  Podell hated it, and so did most of the mobsters. When Darin appeared at the Copa on January 15, 1969, and sang songs that many associated with flower children and the peace movement, some in the audience walked out. This was unheard of at the Copacabana, where landing a ticket was like securing a box seat at Yankee Stadium. The mobsters complained to Podell, and the irascible owner let Darin have it, shouting, “You will never perform here again, do you hear me.”

  According to maître d’ Polameni, there were even jokes and innuendo among the faithful that Darin, because of his new style and musical choices, might possibly get whacked.

  Within a year or so, Darin had changed his tune yet again and appeared one last time at the Copa, in February 1972. He had mostly reverted to his original form, which a reviewer in the New York Times referred to as “Vegas-flashy.” Only now, the mercurial singer’s problem was that, by 1972, the times had passed him by. Perhaps this was still the preferred style of entertainment at the Copa, but to the Times, it was passé: “Darin belongs to another era . . . Where else could he have learned that tired old show-biz routine of whipping off his tie to prove that he was reaching a feverish state of performing energy—a routine that now looks as humorously antiquated as Al Jolson getting down on one knee to sing ‘Mammy.’”

  The mafiosi at the Copa loved the loosened tie bit. What had almost gotten Bobby Darin whacked was “Simple Song of Freedom.”

  13

  The Muck and the Mud

  From the beginning, the Sands Hotel and Casino in Las Vegas was designed to be an offshoot of the Copacabana. Not only was the facility’s primary showroom named the Copa Room, after the Manhattan nightclub, but the man brought in as entertainment director at the Sands was long considered the person most responsible for the creation of the Copa brand. Jack Entratter got his start as a doorman at the Stork Club, one of many New York supper clubs partially owned by Frank Costello. The brain trust at the Copa, another of Costello’s clubs, recognized Entratter’s talents and stole him from the Stork Club by giving him a more prestigious position. At the Copa in New York, Entratter became a manager with a particular emphasis on entertainment. Entratter hired the musicians, comics, and singers, and he hand-selected the Copa Girls, who he openly said did not have to be great dancers, they only had to be beautiful.

  Entratter was six foot four and two hundred forty pounds, a big hulking figure with hands the size of catchers’ mitts. Like Jules Podell, he was a tough Jew, and he could be gruff. But unlike Podell, he had an ingratiating smile, and he never stayed mad for long. The entertainers, in particular, liked Entratter; they felt he was honest with them. And the mobsters liked Entratter because he was big and tough, and he knew to treat them like honored guests when they were in the club.

  Jack Entratter was not a gangster, but he spent his entire career doing business with what the FBI referred to as “Top Hoodlums.” His ability to do this with equanimity made him a treasured commodity in the business, and when, in 1952, a consortium of East Coast mobsters made the commitment to co-finance the Sands on the Vegas Strip, one of their first moves was to transplant Jack Entratter from the Copacabana to the Sands. Thus began a heralded era for the mob—and for jazz—in the Nevada desert.

  Las Vegas was not like other resort towns where the mob had fine-tuned its now classic mix of casino gambling, underworld financing, and live entertainment. Covington and Newport, Kentucky; Atlantic City; Hot Springs; Broward County north of Miami—these were all localities where investments from organized crime and local corruption combined to establish a pattern that was referred by the Kefauver committee as “a threat to the people of the United States.” Vegas was different in that the entire state of Nevada had legalized gambling far back in 1931. Some form of casino gambling had become institutionalized in the state, and there wasn’t much Kafauver and his committee could do about it—though they did try.

  After Havana fell to bearded young revolutionaries in 1959 and the American mobsters were chased off the island, Vegas found itself on the receiving end of renewed attention from the mob. Lansky, Vincent Alo, Moe Dalitz from Cleveland, and Joseph “Doc” Stacher, a mobster who had grown up with Lansky on the Lower East Side of Manhattan who was now based in Los Angeles, had all been major investors in Las Vegas casinos since the mid-1940s. Their baby, the Flamingo Hotel and Casino, whose construction had been mishandled by Benjamin Siegel, leading to his death, nonetheless opened on December 26, 1946. The opening-week entertainment was Jimmy Durante and Xavier Cugat with his Latin jazz orchestra. From the start, it appeared as though the Flamingo was cursed. After Siegel’s murder, the name of the place was changed to the Fabulous Flamingo and ownership passed through numerous hands over the years.