Book: Mafia Spies: The Inside Story of the CIA, Gangsters, JFK, and Castro

Author: Thomas Maier

Reviewed by Paul Varian, retired CNN executive producer

Paul Varian

Gangsters Sam Giancana and Johnny Roselli, who cut their teeth as street thugs for Al Capone, rose to underworld prominence using brutality, cunning and charm.

In 1960, the longtime Mafia pals hooked up with Uncle Sam when they were recruited by the CIA to assassinate Cuba‘s communist dictator, Fidel Castro.

The ill-fated plot, hatched even before the Bay of Pigs fiasco, is the focus of Mafia Spies by investigative reporter Thomas Maier.

It became a debacle in its own right, one event in an endless series of false starts and failures in U.S. policy toward Cuba.

Plans to gun down Castro in a gangland-style ambush or to kill him with exploding cigars, poison pills or lethal James Bond-type gadgets never came to fruition. They were foiled by the perpetrators’ “cold feet,” ineptitude or double agents working for Castro.

The American people first found out about all this 15 years later, during the Senate’s 1975 Church committee investigation of CIA misdeeds. But Maier provides a new level of detail, thanks to recently declassified files on the 1963 assassination of President John F. Kennedy.

John McCone, CIA director under Kennedy, was even kept in the dark. Lyndon Johnson did not learn of the anti-Castro plots until the fourth year of his presidency, and the Warren Commission, which conducted the official investigation of the JFK assassination, was never told.

But Maier is not building a case for JFK conspiracy theorists, just connecting a multitude of dots in a bizarre Cold War drama stretching from Washington and Chicago to Hollywood, Las Vegas, Miami and, of course, Havana — with a cast of characters that could power a limited release TV series: “Boardwalk” meets “Homeland.”

Giancana, a ruthless killer with a hair-trigger temper, took control of the post-Capone Chicago “Outfit” and expanded his influence to the casinos of Las Vegas and suspected criminal ventures in the Midwest, California, Florida, Mexico and elsewhere in Latin America.

Roselli, a suave, well-dressed playboy nicknamed “Handsome Johnny” by his peers, was the Mob’s fixer in Los Angeles and overseer of its Vegas casinos, working closely with Giancana.

He was the first to be approached by the CIA through a middleman, Robert Maheu, who was a private eye, Howard Hughes operative and ex-undercover FBI agent who took “off the books” assignments from the CIA on a monthly retainer.

Roselli fancied himself a “patriot” serving his country and worked directly with Cuban exiles in Miami who wanted Castro dead.

Both Giancana and Roselli were mainly trying to curry favor with the government — a “get out jail free” card, in Maier’s words — and to bring about regime change in Cuba so the mob could reopen its once-lucrative enterprises there.

The two men soon recruited another Mafia chief, Spanish-speaking Tampa boss Santo Traficante, Jr., onetime operator of the mob’s San Souci Havana nightclub, who was arrested and briefly imprisoned after the Castro takeover.

Frank Sinatra, a Giancana friend, makes several cameo appearances in the book. He campaigned for Kennedy in 1960 and introduced him to his then-girlfriend Judy Campbell, who soon became mistress to both Kennedy and Giancana.

After his brief fling with Campbell, Giancana, a widower, became enamored with singer Phyllis McGuire, one of the three McGuire Sisters who were mainstays on the pop charts.

Their relationship brought FBI attention that alerted J.Edgar Hoover to the Mafia-CIA anti-Castro plot for the first time.

After the anti-Castro mission came under congressional scrutiny years later, both Giancana and Roselli were ordered to testify before the Church committee. Giancana never made it. Roselli did, but he soon met the same fate as his old friend.

The last man standing was Trafficante, who hid out in Costa Rica during the Church hearings. Both Giancana and Roselli suspected he may have been one of Castro’s double agents. He died of natural causes in 1987.

Read Mr. Varian’s previous reviews (including a few in the mafia and spy genre):

Books 2018: A Life of Exposing Atrocities, Abuses Through Journalism

Books 2016: From Georgia’s Refuge City Comes a Refugee Soccer Team

Books 2015: Raunchy Mafia Criminality Across 20th-Century America

Books 2014: A Spy Among Friends: Kim Philby and The Great Betrayal

Books 2013: American Witnesses to the Rise of Hitler’s Germany

Editor’s note: This review is part of Global Atlanta’s annual project asking influential readers and community leaders to review the most impactful book they read during the course of the year. This endeavor has continued each year since 2010. Purchases through the Amazon affiliate links at top will provide a commission to Global Atlanta. All books were chosen and reviews written independently, with only mild editing from our staff.