Why did the CIA and Pentagon reach out to Momo Giancana in Chicago when they were planning to whack Castro?

For what it's worth, my guess would be that if they reached out to a NY family, it would have been a topic for discussion at a Commission meeting. Then it would no longer be a secret. And I don't think the FBI and CIA always got along so well when J. Edgar Hoover ran the FBI. I know for a fact the FBI had snitches in NY at the time, Greg Scarpa being the one that comes to mind.

The CIA had connections with Marcello in New Orleans, and Trafficante in Tampa. Through both of them, the CIA made contact with Tommy Lucchese, a New York boss, who in turned helped to try and assassinate Castro, Santo promissed Lucchese a nicely share in the casinos in Cuba once Castro was gone. CIA got in contact with Joe Civello the boss of Dallas through Marcello. CIA got into contact with Giancanna through Johnny Rostelli. Never heard of Gambino being approached, but we may never know the full story of the CIA-Mafia relationship.

Why did the CIA and Pentagon reach out to Momo Giancana in Chicago and not any of the 5 Bosses in New York or the Commission itself when they were planning to whack Castro?

The simplest answer is sometimes the right one.

It could be that Giancana was operating in Cuba.

As GaryMartin pointed out, the Outfit had some well connected and powerful guys.During the mid 50's and early 60's,the Chicago family was the most powerful o.c. group in the U.S. They expanded their operations(legal or illegal) all over the world,including Mexico,Cuba,Panama, Colombia, Ecuador,Jamaica,Western Europe(England,France,Spain,Italy)the Middle East(Israel,Iraq),China and even Japan. Big shots like Manuel Noriega,Ferdinand Marcos,General Omar Torrijos,the Shah of Iran, all received "christmas presents" from the Outfit.The CIA knew about the Outfits connections and they used them to get info’s from all of these countries and to make their own influence around the world.Giancana,Roselli,Larner,Cain took money and at the same time acted like spy’s for the CIA and were feeding the government officals around the world with money and power(informations,weapons etc.) thus making them their own allies. The CIA is a similar organization as the mafia.Giancana reportedly once said that “the CIA and the mob are two different sides of the same coin".

Giancana was overall boss and he gave the "ok".

Roselli was the "go between guy" with the CIA.

Larner had the smuggling contacts and routes around the world and also handeled the financials.

Cain was connected with Central American CIA training camps ad was also a electronic surveillance expert who specialized in telephone tapping and many other things. Cain had tapped the telephones of government leaders on behalf of the Outfit and the CIA.

Later with the downfall of Giancanas administration, the CIA inherited some of their operations and connections, because the new Outfit administration wasnt interested(or maybe they were thrown out) in continuing these operations.

As for the Castro situation,the Outfit guys received money from the CIA but every time they tried to kill Castro,they “allegedly” failed.In other words they swindled the CIA and extort money from it.The infamous CIA-Mafia plots to kill Castro, which were headed by Giancana,Roselli,Larner,Cain along with their partners, Lansky and Trafficante were pure failure.The mob knew if they killed Castro,they still wont get their casinos back because all of the people in Cuba already supported him.They still were goin to have terrorist attacks and that was bad for business.

K

Well-stated and a very nice summary. There will always be questions about this ordeal. But this post is probably the most that is known at this time. There's always the possibility of classified files that have not been made public, but this (IMO) is the most plausible scenario.

Something I would like to know is whether Ricca & Accardo were supportive of Giancana's involvement with the CIA to kill Castro. I've never heard or read anything about their position. Off topic, but I was told that both (Ricca & Accardo) supported Giancana's efforts to influence the 1960 election.

K

Well-stated and a very nice summary. There will always be questions about this ordeal. But this post is probably the most that is known at this time. There's always the possibility of classified files that have not been made public, but this (IMO) is the most plausible scenario.

Something I would like to know is whether Ricca & Accardo were supportive of Giancana's involvement with the CIA to kill Castro. I've never heard or read anything about their position.

JFK assassination writers make the following connections:

Plots against Castro started in the last months of the Eisenhower Administration. They accelerated in the JFK Administration after the Bay of Pigs disaster. JFK took that personally. He appointed the "Cuba Committee" in the CIA and put brother Bobby in charge of it, even though, as Attorney General, he had no statutory authority over the CIA. The CIA contacted Maheu, a former FBI agent with Mob connections. Maheu connected with Roselli, who arranged a meeting with Giancana and Santos Trafficante, the Mob boss of Tampa, FL. Maheu allegedly turned over $100k in CIA cash, plus assorted (and ridiculous) assassination weapons to the two Dons, who presumably would use their Cuban connections to have Castro whacked. The plots and the weapons came to naught.

We have to take this and other accounts of the CIA/Mafia connections with more than a grain of salt because they were never revealed to the Warren Commission, and surfaced much later during the Church Committee and House Select Committee investigations in the late '70s. They were revealed by CIA higher-ups--and we have only their word as to their accuracy.

They were revealed by CIA higher-ups--and we have only their word as to their accuracy.

Giancana wasn't smart enough to know he was dealing with people more treacherous and ruthless than the mafia