Chicanery, 1960 Part IV
The Chicago Outfit
While Richard J. Daley cultivated political power, Salvatore Giancana- the future subject of several famous conspiracy theories- was working his way down, deeper and deeper into the depths of the country’s criminal underworld. He was born in the Smith Park neighborhood of Chicago during the spring of 1908. His parents, Antonio and Antonia Giancana, were Sicilian immigrants. He had seven siblings, and his mother died before his third birthday.
Salvatore “Mooney” Giancana, 1908 - 1975
As a juvenile Giancana joined the “42 Gang”, a street crew associated with Joseph Esposito, the Republican boss of the nineteenth ward and one of the earliest Italian American alderman. When congress passed the “Volstead Act” in 1919, an informal name for the National Prohibition Act, the gang began bootlegging. Within their ranks Giancana stood out as a reliable get-away driver and a high earner. After Esposito was murdered in a drive-by shooting in 1928, Giancana was assimilated into the burgeoning “Chicago Outfit”, recently inherited by a young Al Capone. By then, Giancana, age twenty, was the primary suspect in three different murder cases. A year later, he was convicted of burglary and larceny and served just under four years in the Joliet Correctional Center. Giancana returned to his criminal life after being released. He was back in jail by 1939, this time for bootlegging, and spent another four year stretch at Leavenworth.
H.A. Killian, a close friend of Giancana’s, was associated with New Orleans based crime boss Carlos Marcello. Utilizing this, Giancana influenced liquor license issuance in the city, and as a result, took control of most of the illegal gambling, liquor distribution and political rackets in Louisiana. He also enacted a campaign of violence and intimidation back in Chicago, forcing his surviving rivals to flee the country by the mid-40s. Finally a truly powerful figure, Giancana was named boss of “the Outfit” in 1957. However, he was still expected to consult the organization’s former leaders Paul Ricca and Anthony Accardo about important matters.
Chief consul to the U.S. Senate’s Select Committee on Improper Activities in Labor and Management, Robert F. Kennedy, had announced he would conduct an investigation into racketeering and labor relations in 1956. Famously, he would square off against Teamster Union president Jimmy Hoffa as well as Giancana, who appeared to be amused by Kennedy’s line of questioning. JFK eventually joined to assist his brother with the interrogations, which received extensive media coverage.
The Select Committee on Improper Activities in Labor and Management, 1957-1960
Joseph Kennedy Sr., was said to have opposed their work on the committee, likely due to his own unconfirmed involvement with organized crime. Giancana was among the one hundred Costa Nostra invited to attend the notorious Apalachin meeting at Buffalo underworld fixture Joseph Barbara’s estate in New York that same year. Various topics were allegedly discussed including loansharking, narcotics trafficking and gambling. Sixty bosses were detained and indicted when police raided the event. Giancana was not one of them, but he was heard on a wiretap suggesting that Chicago would’ve been a better place to hold the proceedings considering he had several police chiefs on his payroll.
With the fight against his crooked livelihood ramping up, spearheaded by the Kennedy clan, considerable doubt is cast logically on the suggestion that Giancana would use any of his resources to assist in their quest for power at the start of the new decade. However, rumors have persisted ever since that sometime before the election Joe Sr. struck a deal with the gangster. As Giancana himself is said to have claimed, “I help get Jack elected and, in return, he calls off the heat.” Certainly, this is not totally impossible, although it is highly unlikely that a sitting U.S. senator’s well known father would knowingly risk interacting with a man like Giancana in person or even on the phone without an intermediary. In his book on Giancana, The Don, William Brashler writes that Frank Sinatra, a mutual of the two parties, served this exact purpose. Another book, The Dark Side of Camelot by Seymour Hersh, differs on this point, featuring an account from former Chicago lawyer Robert McDonnell who claims he arraigned a meeting between the two men. McDonnell also, while discussing the votes cast by labor union members, states that “the Outfit” pressured unions to support the Democratic nominee but does not mention if he means locally or nationally. Gus Russo, in The Outfit, says it was only non-Teamsters union members nationally who were pushed to support Kennedy in Illinois, Michigan, Nevada, and Missouri by Murray Humphreys, a politically connected associate of the Chicago mob. This would’ve been because the mob affiliated unions like the aforementioned Teamsters were at odds with Kennedys due to the Senate hearings.
In his 2020 article, Did the Chicago Outfit Elect John F. Kennedy President?, John J. Binder unpacked much of the gossip about the mob’s alleged electoral interference and ran a number of statistical tests to analyze and compare Chicago’s voting patterns in 1960 and circumjacent election cycles. By his determination, the data was not consistent with assertions that “the Outfit” conducted an “all-out” push to get Kennedy into the White House. For example, while the five city wards under the mob’s thumb (the 1st, 24th, 25th, 28th and 29th) definitely voted more Democratic in 1960 than it had four years earlier, so did Chicago as a whole and the rest of the country. This could simply be because Mayor Daley’s machine campaigned harder for Kennedy than it had for the party’s previous nominee.
Binder saw a similar result when he compared 1960 to the 1964. However, like he said himself, his deep dive did not account for local political issues that may have affected the election incidentally, such as “the Outfit’s” supposed involvement in the race for Cook County State’s Attorney, where Dan Ward “defeated” incumbent Republican Benjamin Adamowski. The recount effort in Chicago, which concluded on December 9th 1960- 490,000 paper ballots- unearthed only 943 votes for Nixon, but found 6,186 missing votes for Adamowski. John J Binder, as part of the same statistical tests, observed evidence that in “the Outfit’s” five wards, more votes were cast for Dan Ward than John F. Kennedy, suggesting that Kennedy most likely benefitted from straight ticket voting, but any attempts by criminal forces to “fix” the election were principally directed at Adamowski.
Either way, when confronted with the peculiarities, Mayor Daley tried to dismiss the situation as merely “human error”. A member of the RNC filed a suit, but the case was thrown out of court by Thomas Kluczynski, a Circuit Court Judge connected to Daley who Kennedy later appointed to the federal bench. An appeal was made to the the State Board of Elections, comprised of four Republicans and one Democrat, but they also shot it down, citing the GOP’s inability to provide even one affidavit to support its findings. Eventually though, Mayor Daley was forced to allow a special prosecutor to conduct their own investigation. This man, Morris Wexler, would bring charges against over 600 polls workers and precinct captains. A downstate judge was brought in, but was unconvinced and dropped the case.Over the years it has become increasingly regarded as fact that organized crime in Chicago, called “the outfit” played a role in Kennedy’s win in 1960. While this is a bit of a leap, there’s also no real way to definitively say that there was no criminal influence on the election, at least in Chicago.
Works Cited
Allswang, J.M. (2019) Bosses, machines, and urban voters. Baltimore, MD, Baltimore, MD: Johns Hopkins University Press, Project Muse.
Binder, J.J. (2020) ‘DID THE CHICAGO OUTFIT ELECT JOHN F. KENNEDY PRESIDENT?’, themobmuseum.org, 22 October. Available at: https://themobmuseum.org/blog/did-the-chicago-outfit-elect-john-f-kennedy-president/.
Bomboy, S. (2017) ‘The drama behind President Kennedy’s 1960 election win’, constitutioncenter.org, 7 November. Available at: https://constitutioncenter.org/amp/blog/the-drama-behind-president-kennedys-1960-election-win (Accessed: 01 October 2024).
Carlson, P. (2000) ‘Another Race To the Finish’, The Washington Post, 17 November.
Cheney, K. (2022) ‘See the 1960 Electoral College certificates that the false Trump electors say justify their gambit’, POLITICO, 7 February.
Royko, M. (1988) Boss: Richard J. Daley of Chicago. New York: Plume.
Shesol, J. (2022) ‘Did John F. Kennedy and the Democrats Steal the 1960 Election?’, New York Times, 18 January.