With Luciano’s conviction in 1936 and Genovese fleeing to Italy due to murder charges, Costello became “Boss” in 1937 – albeit reluctantly. He had not been idle while waiting in the wings. Cementing ties in the crime world he was instrumental in organizing the first nationwide crime-syndicate meeting in 1929 in Atlantic City – bringing in crime bosses from around the country. Legend has it that during this meeting – just months after the St. Valentines’ Day Massacre – Costello pulled Capone aside to offer some advice. He chided Big Al for drawing attention to the “family business” with the killings and strongly recommended Capone turn himself into authorities to quell both the public outrage and law enforcement attention. Capone reacted as expected – unfavorably - but just weeks later did just as Costello suggested, surrendering to authorities in Philadelphia on a gun possession charge and serving nine months in jail beginning in August 1929.
Costello had also continued to grow his political network. He attended the 1932 Democratic National Convention with NY City Mayor Jimmy Hines and met Presidential candidate Franklin Roosevelt. When FDR took office and repealed Prohibition Costello was prepared, having diversified into gambling, numbers and slot machines - pulling in millions of dollars a year. When Fiorella LaGuardia became NY City Mayor in 1934 and very publicly went after organized crime and specifically Costello’s slot machines, Costello had a contingency plan - specifically a Louisiana politician he had met under less than auspicious circumstances. At a gala several years earlier, Costello had entered the Men’s Room and found a very drunk Huey Long, who frustrated at the single toilet facility was attempting to relieve himself by urinating between the legs of the gentleman if front of him. Inevitably a heated if not dampened fracas began, but Costello – living up to his nickname “The Prime Minister” - was able to calm both parties before any serious trouble ensued. Now in 1934 he contacted Long, who greeted him with open arms and Costello moved his slot machine operation to the state of Louisiana. So without missing a beat and partnering with Lansky and Siegel, the three now built a gambling empire that stretched down to Louisiana, Florida, then Las Vegas and Cuba.
If accommodation and the velvet glove didn’t work, Costello could also rule with an iron fist when necessary. When Abe “Kid Twist” Reles, a hit man and part of Murder, Inc, was arrested and then began talking to authorities, Costello acted both characteristically and decisively. After talking to the authorities Reles was holed up in a Coney Island hotel under a 24 hour guard. On November 12th, 1941, two of the policemen outside Reles’ door “fell asleep” and Reles fell six stories out of his hotel window to his death. Luciano later claimed it cost Costello $50,000, Lansky claimed twice that, regardless, Reles became known as the canary that could sing but couldn’t fly and the problem was solved.
As we’ve seen Vito Genovese returned to the county at the end of World War II and began scheming to get Costello’s job as “Don”. Costello was both respected and well liked by his underlings so Genovese had to be both patient and smart – not two of Don Vito’s foremost traits. By this time – 1946 - Costello was conservatively making a million dollars a year, had removed himself from the day to day operations of the crime family and was investing in non-criminal activities and assets – further frustrating Genovese. Costello was looking for respectability in high society and allegedly began seeing a psychiatrist – a la Tony Soprano – for assistance in dealing with conundrum.
In 1950-51 Costello’s hopes for respectability came crashing down with Tennessee Senator Estes Kefauver’s hearings on organized crime. Costello was called to testify – broadcast on national TV - and he and his reputation never recovered. Soon after the hearings Genovese had Costello’s right hand man, Willie Moretti, assassinated – for “talking” before the Senate Committee. Costello soon found himself embroiled in one court battle after another, including a contempt charge, the result of walking out of the Kefauver Hearings. He served 14 months, was released, and then rearrested on tax evasion charges in 1954. He served 11 months, was released on appeal and then rearrested in 1956, sent to prison again and released in 1957 on appeal.
On the sidelines Genovese continued plotting against Costello, forming alliances with threats and bribes. On May 2nd, 1957, and just after Costello’s release from prison, Vincente “The Chin” Gigante – on Genovese’s orders – met Costello in the lobby of his Manhattan apartment building and shot him in the head. Miraculously Costello survived with a painful scalp wound, but it was enough for Costello. He turned over the reins to Genovese while keeping his gambling and legitimate interests intact – which is probably all Costello wanted at that point.
The Prime Minister of the Underworld now “retired” to his Waldorf Astoria penthouse in Manhattan but was regularly visited by the likes of Carlo Gambino and Tommy Lucchese. His old friend Meyer Lansky - who had his own problems with the law - stayed in touch but less openly. Costello’s experience and wisdom were still valued by the underworld and his opinions respected. He died at the age of 82 of a heart attack on February 18th, 1973.
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