“I looked at him and said, ‘If being a star means being like you, then I don’t want it.’”

  Sinatra’s baby blue eyes turned cold.

  At four o’clock that morning, walking through the mostly deserted lobby of the hotel back to his room, Greene was attacked by three men: Joe Fischetti and two of Sinatra’s bodyguards. Fischetti pummeled Greene with a blackjack. The comic gave as good as he got: “Fischetti, that fuckin’ moron—I split his whole face open.”

  Word quickly circulated about the attack. Both Sinatra and Fischetti became worried that Greene would go to Giancana, his friend, and that Momo would be angry. According to Greene, Sinatra begged him to let it drop. He offered the comic a role in his next movie. Greene found it all pathetic, but according to the morality of the streets, a man didn’t snitch. When Giancana called him on the phone to find out what had happened, Greene said he fell down some stairs.

  Was Sinatra, after years of endearing himself to thugs and hoodlums, simply indulging in behavior that he thought was emblematic of those mob bosses whom he seemed to admire? Was he reveling in what he felt was his inheritance as an honored player in that dark place where jazz and the underworld came together in business and, occasionally, in violence?

  In his career, Old Blue Eyes had done something singular: He had crossed over from being a worker on the plantation to being a plantation owner. With Reprise Records, a movie production company, ownership points in casinos—true power—Sinatra was beholden to very few people in the music business. He was the padrone he had always dreamed of being. No one—not Louis Armstrong, Duke Ellington, Billie Holiday, or any other monumental figure in the history of the music—had been able to achieve what Sinatra had achieved. His talent had been his opening salvo, and though he often protested that his Sicilian American heritage was used against him by bigots, his ethnic entrée with the mafia—and his desire to emulate the very essence of those who dwelled there—was at the core of the matter.

  Freedom Now Suite

  Black jazz musicians did not have Sinatra’s sway. In jazz and most other endeavors in American life circa the 1960s, being Black was a mitigating factor. The very words “Negro” or “Black” were meant to be qualifiers. Billy Eckstine, whom some thought was on a par with Frank as the greatest living jazz vocalist, was sometimes referred to as “the Black Sinatra.” Nobody referred to Sinatra as “the White Billy Eckstine.”

  For some Black musicians, there seemed to be only one alternative: exile. Operating within a racist society, in a business that was under the thumb of gangsters, was debilitating. Pianist Mary Lou Williams, whose sublime talent and artistry had been in evidence since she was eight years old, compared navigating the business of jazz to slogging through the muck and the mud. Choosing to leave your own country was not an easy call; it could be disorienting, lonely, and heartbreaking. But to some, not living as a second-class citizen made the prospect of life as an artist in Paris, Amsterdam, or, later, Japan seem attractive. In these environments, African American jazz musicians were not viewed as chattel. They felt appreciated. Said saxman Dexter Gordon, “I never got a bouquet of flowers in my life before I went to Copenhagen. The first time, I thought, ‘What does this mean?’ I wanted to give it back. It was so totally unexpected.”

  Along with Gordon, many others chose to live and perform in exile: Sidney Bechet, Lester Young, Bud Powell, Coleman Hawkins, Benny Carter, Johnny Griffin, Don Byas, and Mal Waldron, to name a few.

  At home in the States, others tried to create alternative pathways through the system.

  In 1952, bassist/composer Charles Mingus, his wife, and drummer Max Roach launched Debut Records. Both Mingus and Roach had tired of working under the likes of Mo Levy and other mob-connected producers and record label owners. Based in Brooklyn, Debut was designed to be a collective where artists owned their own masters and received actual royalties (terms that Sinatra would later promise but never fully deliver with Reprise Records).

  Mingus, who had been toiling in the business for two decades, was not averse to dealing with gangsters. He was managed for a time by Joe Glaser. Mingus admired Glaser’s tough-talking ways, but in the end, like so many other musicians who aligned with Glaser, he felt he was being played for a fool.

  Almost by accident, one of the first recordings for Debut Records was Jazz at Massey Hall, a live recording by a group comprised of Mingus, Roach, Charlie Parker, Dizzy Gillespie, and Bud Powell. This collection of some of the most renowned bebop artists performed under the name the Quintet. Their performance at Massey Hall in Toronto was the only time they performed live together; it is viewed by some as the greatest jazz album ever recorded. Said Mingus proudly, “That [album] is what put Debut on its feet, even though the percentages went to the musicians. Debut only got 10 percent but we still made money on that. I didn’t take anything. Max didn’t take anything. So the royalty went back to the company. Each musician got [equal shares], minus the 10 percent. The record got a lot of publicity and sold a lot of copies.”

  The very idea behind Debut Records was to create greater autonomy for Black jazz musicians. Roach, an intense Brooklynite, originally born in North Carolina, was among the first of his generation to think of jazz in Black nationalist terms. Along with the record label, he started a social club in Brooklyn. The Putnam Central Club, on Putnam Avenue, was headquarters for the label and the genesis of the Jazz Composers Workshop. The workshop staged a series of concerts and rehearsals performed by many of the biggest jazz names in New York: Thelonious Monk, Art Blakey, Kenny Clarke, and others.

  The objective was to create a loosely organized group of musicians interested in collaborative composition and cooperative economics. The record label and workshop were an unprecedented effort to break free from the shackles of the jazz slavemasters, but Mingus, in particular, ultimately gave in to the very impulses he was seeking to escape. In an effort to create leverage with club owners and record executives, he had notorious Brooklyn gangster Joey Gallo serve as his agent.

  “Mingus, what did you do to me?” said an executive from the Brunswick label one day. “I just asked you to do a record date. You didn’t have to send the gorillas after me.”

  The bassist was unapologetic. “You’re the gorilla, man, you walk around making me [subservient] to you.”

  “Look, you got the Gallo brothers after me, man. What are you trying to do to me? These guys will kill you. They’ll kill you and me too.”

  Afterward, Mingus had to admit that he didn’t fully comprehend with whom he was dealing when he hired the Gallo brothers. When he was reminded by Joey Gallo that he had signed a binding contract that tied him up in perpetuity, Mingus became concerned. In 1955, he famously checked himself into Bellevue Hospital. He later said in interviews that it was because he believed Bellevue was the one place the Gallo brothers could not track him down and kill him.

  After being released from the hospital, Mingus divested himself from the short-lived Debut Records. The label was soon bought out by a larger company.

  Trying to break the chains of subservience on the business side was one thing, but also there was the music itself.

  Ever since Billie Holiday first sang “Strange Fruit” in Greenwich Village in 1939 at Café Society—a club that was not mob-controlled—people recognized that jazz had the potential to express complex concepts about humanity. The emotional content came from the blues. Personal hardship, the vicissitudes of life, injustice, heartbreak—these were the emotional elements that brought the blues to life. “Strange Fruit” added a sophisticated level of poetry; metaphor, simile, and Billie’s voice were used to burrow deep into the conscience of the listener. Some thought that Holiday’s interpretation of the lyrics would change jazz forever by summoning new realms of protest, commentary, and righteousness in the music. The song did have an impact, though it was more cultural than musical. Jazz was not equipped to incorporate politics and civil protest into its business plan, at least not as the business was currently constituted or had been since the earliest days of Storyville.

  Those who owned the preeminent jazz venues—the Copacabana (Costello and Podell), the 500 Club (Skinny D’Amato), Chez Paree in Chicago (Giancana), Ciro’s on Sunset Strip in Los Angeles (mobster affiliate Billy Wilkerson), the Sands (Lansky, Alo, and others)—were not interested in music with a social consciousness.

  By the late 1960s, this had become a conundrum. Some musicians felt that the business of jazz could never be fully liberated until the music itself was liberated.

  The clarion call was Freedom Now Suite, an album by Max Roach and his future wife, singer Abbey Lincoln. Officially titled We Insist! Max Roach’s Freedom Now Suite, the album was a precursor of the Black Power movement. Musically avant-garde, angry, thematically ambitious, the five compositions on the album constituted a howl of rage and anguish—literally—as Lincoln screams over Roach’s drum solo for a full twenty seconds in one section of the record.

  The album was not a hit, and it scared some people. When the music was performed live at the Jazz Gallery in Manhattan for an audience of largely NAACP members, the audience was respectful, but no one was dancing or clapping along with the beat. They were not there to be entertained.

  Roach’s album did open up an avenue of expression that others followed. The Student Nonviolent Coordinating Committee (SNCC) established its own band, the Jazz Pioneers. John Coltrane’s composition “Alabama” was a searing response to the infamous Birmingham church bombing of 1963, where four little girls were murdered. Nina Simone, the African American chanteuse, sang “Mississippi Goddamn,” an appropriately angry condemnation of the current condition. Pianist Randy Weston incorporated more explicitly African elements into his music. Others followed. Don Cherry explored the music of India in his work. Sonny Rollins, Yusef Lateef, Pharoah Sanders, and others explored rhythmic elements from a myriad of cultures, especially those that reflected on African roots. Often, this music was meant to be spiritually enlightening as much as entertaining.

  Behind this movement was a growing suspicion on the part of some musicians that the way the music was presented to the public was a big part of the problem. Smoky basement clubs owned and run by gangsters, for many, cast aspersions on the music. As Abbey Lincoln put it:

  I’m jealous when I see ballet dancers in their settings or classical musicians in their setting. That’s when you bring your best, not when you’re in a smoky, dark, funky room without a dressing room. I railed and railed about that . . . Jazz rooms were [originally] brothels where people with shady characters come and pick up each other . . . The sound [in these places] is an abomination . . . There’s nothing romantic about poverty, and that’s what these joints are.

  Attempts to sustain a more politically oriented version of jazz were mixed. In a commercial environment in which the profit motive was king, gangster-affiliated club owners and record labels were ambivalent, at best, or more likely openly hostile to the distribution and dissemination of what some jazz journalists referred to as “free jazz.”

  The Freedom Now Suite was a universe away from the Copa Room at the Sands, and that was just the way the mobsters wanted it.

  A Matter of Respect

  At 12:50 A.M. on the morning of July 16, 1972, mafia boss Tommy Eboli was shot in the head and body after leaving the apartment building of his gumare (“mistress”) in Crown Heights, Brooklyn. On Lefferts Boulevard, he quickly bled out and died. At the age of sixty-one, his soul, according to Sicilian Catholic belief, rose from his body and either ascended skyward into the heavenly embrace of his ancestors, or descended unto Hades, where previous dead mobsters were no doubt awaiting his arrival.

  Eboli’s driver was not killed in the shooting. It was later determined that he most likely had been in on the hit.

  Few men were more startled by the boss’s death than Mo Levy. In the three years since Eboli had taken over as godfather of the Genovese family, the record executive had been deepening his relationship with the capo in chief. In the spring of 1971, he even took the extraordinary measure of traveling to Europe to meet with Eboli in his home country of Italy. Eboli was already there, meeting with family and “business associates.” Levy and Eboli met in Naples, traveled together by train to Southampton, England, and then to London, where they boarded the SS France, an ocean liner. On a three-day trip across the Atlantic, the mafia boss and the music mogul no doubt discussed their various joint ventures, analyzing and dissecting ways that they could slice chunks of blubber from the humpback whale that was the American music business.

  The entire trip was surveilled and memorialized by FBI agents in a series of reports that were added to Levy’s case file.

  Following Eboli’s murder, two agents interviewed Levy. The record exec was polite with the agents. “Levy said he knows of Eboli’s reputation in the underworld but attributes a large part of this to exaggerated newspaper copy.” Levy admitted to his business partnerships with the crime boss, noting that Eboli owned 50 percent of Promo Records. “Although almost illiterate,” said Levy, “Tommy had a good business head and was an able worker.” Levy claimed to have no idea who would have wanted to snuff out the life of Tommy Eboli.

  The FBI for a time deactivated their investigation of Mo Levy. For ten years, they’d had the man under surveillance, with informants in his offices at Roulette Records, IRS agents scrutinizing his financial ledgers, and assorted criminal snitches feeding them gossip and rumors about Levy, who by now had become a living legend. The Feds had everything—except criminal charges.

  The case against Levy didn’t stay deactive for long.

  On an evening in 1975, Levy was leaving the Blue Angel nightclub with a girlfriend and a business associate. A passerby made a flirtatious comment to Levy’s girlfriend. The record exec and his associate attacked the man, who, unbeknownst to them, happened to be an off-duty police officer. A police report of the incident stated that Levy’s associate held the man down while Levy viciously pummeled him in the face. The off-duty cop lost an eye.

  Levy was charged with assault. But, as a man with connections, he was able to make it all disappear. Charges were dismissed before the case reached court, and all records were expunged. A related civil case was settled out of court.

  Levy may have escaped criminal charges, but his actions rekindled scrutiny by the FBI. Once again, they assigned agents and cultivated informants.

  Though Roulette Records seemed to be up to its neck in debt, Levy was as active as ever. He branched out by founding a company called Strawberries Records, which, by the early 1980s, had established itself as a highly profitable record store chain specializing in bargain-priced LPs and overstock from corporate record labels. The FBI believed that Levy’s ownership of Strawberries was a front for the latest boss of the Genovese crime family, Vincent “the Chin” Gigante.

  By the late 1970s and 1980s, there were few remaining mafiosi in New York as renowned as Vinny the Chin. Born in the Bronx, Gigante first became an up-and-comer with the Honored Society while still a teenager. His first major act, in 1957, was the attempted assassination of mob boss Frank Costello, Prime Minister of the Underworld. Gigante was eighteen and primarily a modestly talented cruiserweight boxer. He fired a pistol at Costello in front of his apartment building on Central Park West. The bullet skimmed Costello’s head but did no further damage.

  According to underworld lore, Gigante had been hired to shoot Costello by Vito Genovese, who was looking to move Costello aside. The teenage Gigante was arrested at the scene of the crime and put on trial, but Costello, who had very clearly seen Gigante fire the shot that creased his skull, claimed on the witness stand that he “didn’t see nothin’.”

  Gigante walked free. He transitioned from being a boxer to becoming a made man. A big hulking figure with a broad chin (thus the nickname), he positioned himself to rise in the family, until he was taken down by prosecutors in the same narcotics case that put Genovese behind bars. Gigante was locked up and served eleven months; he was able to secure his release in a way that would shape the direction of his criminal career for the next thirty years. Through his lawyers, Gigante got a criminal psychologist to declare him mentally unstable and therefore not responsible for his actions. This medical diagnosis was accepted by a district court judge, and Gigante was set free.

  The young gangster had been declared crazy, but he was, perhaps, crazy like a fox. Gigante spent the next three decades occasionally wandering his Greenwich Village neighborhood in a bathrobe and slippers, unkempt and unshaven, looking very much like, well, a crazy person. The FBI was convinced that it was all a ruse; the wily mob boss was simply burnishing a future insanity defense. Not only did the Feds have information that the Chin was fully compos mentis, they believed he was a high-ranking member in the Genovese family, and among his business partners was Mo Levy: “Gigante controls by threats of force and induces Levy to participate in financial transactions on behalf of Gigante and the Genovese LCN [la cosa nostra] Family . . . Gigante has developed a stranglehold on Levy’s recording industry enterprises, in effect turning Levy into a source of ready cash for the Genovese LCN Family and its leader.”

  Meanwhile, Levy still had a record empire to run. By the mid-1970s, jazz was no longer a major aspect of Roulette Records. Even so, Levy remained devoted to the music that had launched his career. Since the earliest days of Birdland, presiding over the club with his brother—who had literally shed blood and given his life for jazz—Levy saw himself as a jazz purist. He was not interested in diluting the music with rock and roll or funk (that is, “fusion” jazz), as some record producers had begun to do; he preferred going back to the music’s roots.

  In 1976, Levy reached out to Betty Carter, a forty-seven-year-old bop-influenced vocalist whose prodigious gifts evoked the spirit of her antecedents Billie Holiday and Sarah Vaughan. Carter was a dynamic singer with startling range who happened to be practicing her art at a time when audiences for undistilled jazz were in remission. Not only did the singer not currently have a record deal, but she also didn’t even have a manager.