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Johnny Roselli: Larger Than Life Mystery Mobster

John “Handsome Johnny” Roselli (born Filippo Sacco); (1905-1976), was an influential mobster for the Chicago Outfit who helped that organization control Hollywood and the Las Vegas Strip.

In the early 1960s, Roselli was recruited by the Central Intelligence Agency (CIA) in a plot to assassinate Cuban leader Fidel Castro. He is suspected by reality theorists of being the lead Mafia role player in the JFK assassination.

Roselli was a mysterious shape-shifter who kept bumping into the 20th century’s biggest figures.

Roselli moved to Los Angeles in 1924, and began his California criminal career working for small-time bootleggers, becoming the top truck driver for Tony Cornero. Eventually, Roselli was promoted to working closely with the Cornero brothers in securing the liquor imports into Southern California.

He then launched his lifetime role as a fixer by bribing and securing the loyalty of Orange County officials, opening up their ports for the gang’s use. In 1926, Roselli went independent and became further involved in several LA area vice rackets, especially prostitution and gambling.

Roselli first met Al Capone in 1927, on a trip to Chicago to attend the Jack Dempsey-Gene Tunney Boxing match. In 1928, Capone invited Roselli back to Chicago, this time offering him a role in his organization. Roselli was tasked with working with the Los Angeles crime family, as a fixer and facilitator of Capone’s investments.

One industry where the Mob laundered it’s money was Hollywood. Roselli was also close friends with Columbia Pictures co-founder Harry Cohn and Jack Warner. Roselli’s close relationship with Cohn, who himself had a reputation within the industry as a tyrannical boss and an abusive predator and womanizer with an affinity for Mussolini, directly brought part of Columbia under mob control.

New Jersey Jewish mobster Abner Zwillman, was the partner of Lucky Luciano and Meyer Lansky. When Cohn needed funds to quickly to buy out his terminally ill business partner and co-founder of Columbia Joe Brandt, Roselli pointed him to Zwillman who facilitated the cash for the takeover in exchange for a secret and silent slice of the studio pie. Zwillman held control over Cohn until his mysterious death by hanging in 1959.

Roselli had a dapper and engaging style that ingratiated him with show business. He dated and seduced numerous Hollywood starlets and later introduced his Boss Sam Giancana to his friend Marilyn Monroe- with whom he had an affair. He was a secret investor at Eagle Lion Productions, run by Bryan Foy, a former producer for 20th Century Fox.

Roselli, as Capone’s and ultimately Meyer Lansky’s representative on the West Coast, passed a fortune in mafia investments to Harry Cohn and Bugsy Seigel who pooled gambling investments with Billy Wilkerson, publisher of the Hollywood Reporter.

Lee Server’s biography, “Handsome Johnny: The Life and Death of Johnny Roselli, Gentleman Gangster, Hollywood Producer, CIA Assassin,” said Roselli moved between those two worlds — Hollywood and organized crime — “at the highest levels.”

In July 1933, the Mob installed Frank L. Shaw as Los Angeles mayor. This terminally corrupt administration set up a graft operation whereby the underworld paid regular bribes directly to City Hall.

Roselli emerged as the go to fixer and liaison between the mayor’s office and the various gangs and individuals who sent regular payoffs to city hall. This favored position with the city government helped to position Jack Dragna’s LA Mob organization as the preeminent criminal organization in Los Angeles under the Shaw administration.

He worked closely with mobster Willie Bioff to extort the studios throughout the 1930s. Bioff’s racket was to control the trade unions and demand regular payoffs from the studios to avoid strikes. It was a simple shakedown, and it worked well — at least until a handful of studio executives testified against him.

Roselli’s run of luck temporarily ran out as he served four years in prison from 1943-1947.

After his release Roselli was the behind the scenes producer of several film noir movies that are considered cult classics.

In the mid-1950s, Roselli shifted his focus away from Hollywood and toward the fast-growing and highly profitable gambling mecca, Las Vegas, Nevada. By 1956, Roselli had become the Chicago and Los Angeles mob’s chief representative in Las Vegas. His job was to ensure that the Chicago mob bosses received their share of the burgeoning casino revenues through “skimming”.

In 1957 he arranged the financing and operations of the Tropicana and Royal Nevada casinos for the New Orleans, Chicago and New York Mob.  He arranged for Mafia figures in Detroit and St. Louis to buy into the Frontier Hotel and later was instrumental in the sale of the Sands and Desert Inn to Howard Hughes, for which he got $95,000 in finder’s fees. The money came from the Teamsters Central States Pension Fund, controlled at the time by Chicago mobster Paul “Red” Dorfman.

Working for new Chicago boss Sam Giancana, he became the gambling mecca’s behind-the-scenes boss, running the town from his suites and poolside tables at the Tropicana and Desert Inn, enjoying the Rat Pack nightlife with pals Frank Sinatra and Dean Martin. His company monopolized talent bookings in Las Vegas.

In 1963, singer Frank Sinatra sponsored Roselli for membership in the exclusive Los Angeles Friar’s Club. Soon after his acceptance, Roselli discovered an elaborate card-cheating operation run by one of his Las Vegas friends, Maurice Friedman, and asked for his cut. The card cheating was finally discovered in July 1967 by FBI agents tailing Roselli. Scores of wealthy men, including millionaire Harry Karl, the husband of actress Debbie Reynolds, and actor Zeppo Marx, were bilked out of millions of dollars.

Roselli was instrumental in arranging for Howard Hughes to move to Las Vegas and for getting him the top floor of the Desert Inn Hotel. But later, when Roselli approached Hughes aides for a $50,000 loan, he was turned down. Roselli needed the $50,000 for legal fees for his role in the card cheating operation at the Friar’s Club in Hollywood.

He was convicted and sent to the Federal prison in McNeil Island, Wash., where he did not stand up well to the rigors of prison life, according to his friends.

In 1971, Mr. Roselli was brought from prison to testify before a grand jury looking into Mafia ownership of the Frontier Hotel. Mr. Roselli at first refused to answer on constitutional grounds, but he was given immunity. Faced with the prospect of having more time added to his sentence, he agreed to cooperate when promised that his testimony would be kept secret.

His information led Federal investigators to Maurice Friedman (same guy behind the Friar’s Club cheating), the developer of the Frontier, who testified that Anthony Giordano, the Mafia boss of St. Louis, and Anthony Zerilli and Michael Polizzi, Mafia captains in Detroit, held hidden interests in the casino.

Judith Campbell Exner

Described by one informant as “sex crazy,” Roselli was close to Judith Campbell Exner, a socially active California freelance artist who became involved with both President John F. Kennedy and Chicago mobster Sam Giancana. Over time, when all this became public, these romances shined an accusatory spotlight on the troubling link between politics and organized crime.

As Roselli continued to work in and around Hollywood and Las Vegas, the gangster eventually got to know Sinatra and Kennedy, who was soon to be president.

In the most fascinating section of  Server’s book, there are details on how Roselli was recruited for a secret plot to assassinate Fidel Castro in Cuba.

Initially he was sent to Havana for several months in 1958 to conduct quality control functions for the Outfit at their casinos. This was before Castro took power and nationalized the casinos without compensation.

According to the Family Jewels documents released in 2007, members of the Mob were involved in CIA attempts to assassinate Cuban leader Fidel Castro. The documents showed that, in September 1960, the CIA recruited Robert Maheu, an ex-FBI agent and aide to Howard Hughes in Las Vegas, to approach Roselli under the pretense of representing international corporations that wanted Castro dead due to lost gambling interests.

Roselli introduced Maheu to mobster leaders Sam Giancana and Santo Trafficante Jr.

In September 1960, Richard Bissell and Allen W. Dulles, the director of the Central Intelligence Agency (CIA), initiated talks with two leading figures of the Mafia, Roselli (using the name John Rawlston) and Sam Giancana.

On 12th March, 1961, William Harvey arranged for CIA operative, Jim O’Connell, to meet Sam Giancana, Santo Trafficante, Johnny Roselli and Robert Maheu at the Fontainebleau Hotel. During the meeting O’Connell gave poison pills and $10,000 to Rosselli to be used against Fidel Castro.

There is every indication that Roselli was involved in executive action black ops well before the Castro and JFK plots.  From Charles Rappleye, All-American Mafioso: The Johnny Roselli Story (1991)

Two sources who said they worked with Roselli on frequent occasions in Guatemala…. The first source… an underworld operator… said he joined Roselli in Guatemala City and Mexico City on half a dozen separate trips beginning in 1956. Mexico City served at the time as a nerve center for plots in Guatemala, which borders on Mexico… and as the base for all CIA operations in Central America…. The second source was a longtime government field worker assigned to Guatemala with the International Cooperation Administration (ICA)…. The ICA source was extremely reluctant to talk, but confirmed that he had become acquainted with the underworld source in Guatemala, and Roselli had been “a major force” beneath the surface of events in Guatemala City and in other states in Central America. “John had access to everyone and everything that was going on there,” the government source asserted. That included the fruit companies, the Guatemalan Army, and the American delegation… According to both sources, Roselli’s primary concern in Guatemala was to protect and advance the interests of Standard Fruit and Steamship Company.

With the various contacts and relationships thus established- this set up Roselli’s role to be intimately involved in the JFK assassination. He was in Dallas on that fateful day. Previously he had been dispatched by Giancana to New Orleans to size up the potential of Lee Harvey Oswald as a patsy. Oswald was involved with the Marcello organized crime operation there. Jack Ruby, aka Rubenstein, was also a point man for the Giancana crime network in this operation. Ruby and Oswald knew each other.

Bill Bonanno, the son of Cosa Nostra mafia boss Joseph Bonanno, claimed in his 1999 memoir, Bound by Honor: A Mafioso’s Story, that he had discussed the assassination of Kennedy with Roselli and implicated him as the primary hitman in a conspiracy instigated by the mob.

In 2010, Playboy magazine published an article by Hillel Levin in which Roselli was also implicated in the assassination by Robert “Tosh” Plumlee and James Files. Files was one of the shooters on the scene in Dallas. More on the Roselli and Files role in the JFK assassination is in our post. Video below of Files discussing the role players of the JFK assassination.

John F. Kennedy’s Prescient Belief in Conspiracies and His Own Demise

On June 24 and September 22, 1975, Roselli testified before the 1975 U.S. Senate Select Committee on Intelligence (SSCIA) led by Idaho Senator Frank Church about the CIA plan to kill Castro, Operation Mongoose.

Shortly before Roselli testified, an unknown person shot and killed Giancana in the basement of his Illinois home. This happened just days before Giancana was to testify before the committee. Giancana’s murder supposedly prompted Roselli to permanently leave Los Angeles and Las Vegas for Miami, Florida.

On April 23, 1976, Roselli was called before the committee to testify about a conspiracy to kill President Kennedy. Three months after his first round of testimony on the Kennedy assassination, the Committee wanted to recall Roselli. However, at this point, he had been missing since July 28.

This astonishing ride came to an end in 1976, when the 71-year-old mobster was killed, cut up, and stuffed into a 55-gallon oil drum later found floating in a bay near Miami.

Jack Anderson, of the Washington Post, interviewed Roselli just before he was murdered. On 7th September, 1976, the newspaper reported Roselli as saying : “When Oswald was picked up, the underworld conspirators feared he would crack and disclose information that might lead to them. This almost certainly would have brought a massive US crackdown on the Mafia. So Jack Ruby was ordered to eliminate Oswald.”

Two men known to have had personal knowledge of the circumstances of the murder have provided solid information that Roselli was killed by members of the underworld as a direct result of his testimony before the Senate committee. (New York Times)

Roselli, however, was not so conscientious about clearing his Senate testimony with his Mafia associates, according to a high‐ranking Mafia figure, and it was this infraction that led to his death.

“When you’re called before a committee like that, you have to go to your people and ask them what to do,” the Mafia figure said. “Roselli not only did not come to us he went before the committee and shot his mouth off all over the place.”

He said Mafia leaders had been angry with Mr. Roselli since 1971 when he appeared before a Federal grand jury in Los Angeles investigating underworld involvement in the Frontier Hotel. Three Mafia leaders went to prison as a result of that investigation, and Mr. Roselli was suspected—correctly, as it turned out—of having secretly provided information to the prosecution.

The Mafia figure said that shortly after Mr. Roselli’s first appearance before the Senate committee on June 24, 1975, his murder was approved by the commission of bosses that sets policy for the 26 Mafia families in the country.

4 Comments on Johnny Roselli: Larger Than Life Mystery Mobster

  1. Roselli (according to grassy knoll shooter James Files) was flow into Dallas on 11/21/63 aboard a CIA airplane. No doubt he coordinated events for the Outfit’s role and got shooter Charles Nicoletti into the Dal-Tex building for a triangulated shot which probably was the neck shot that hit Kennedy initially. Roselli probably handled all the necessary connections between Chicago, Tampa, New Orleans for Allen Dulles.

    JFK was a highly compartmentalized operation between the CIA (Dulles). Secret service (Cord Meyer), Dallas PD (Marcello) and LBJ.

    No doubt the Dallas PD had set out to kill Oswald when he fled out of the TBD running to the Texas theatre, but Oswald smelled a trap and claimed publicly he wasn’t resisting. That made him Ruby’s problem.

    The rest as they say is history.

      • For those with alternate shooter theories or questioning Files recounting of events, remember Files maintained he left the .221 shell casing sitting on the fence top in the grassy knoll after he bit down on the brass casing.
        A .221 shell casing was found with teeth marks (I believe around 1986) by a person with a metal detector in that grassy knoll area, buried about 6” down. That pretty much proves Files recounting of events.

  2. If you guys have not seen Everything is a Richman’s Trick JFK ) 9/11.Here is is. I thought he did a good job on the JFK part/

    the video shows someone from the sewer also along with the other places. I found this letter from a Private investigator that was supposedly sent to Jim Garrison saying he thought JFK was shot from the sewer
    https://www.onthetrailofdelusion.com/post/was-jfk-shot-from-a-sewer. I guess people had heard that before but the video names the men’s name as Lamont and the guy as Jack along with a lot of the other names mentioned. Just food for thought it no one has seen these 2 items together

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