Background & Context

• CIA executed 600+ assassination attempts on Cuban leader Fidel Castro, all unsuccessful
• Gerald Ford signed Executive Order 11905 prohibiting US government employees from political assassination
• Castro became Cuba's first communist leader in Western Hemisphere
• Castro studied law at University of Havana, participated in resistance movements in Dominican Republic & Colombia
• Organized guerrilla warfare against dictator Fulgencio Batista in 1950s
• Forced Batista to flee in 1959, became prime minister for 17 years, president 1976-2008
• Cuba aligned with Soviet Union, concerning US due to proximity to Florida
• Fabian Escalante (Cuban secret service head) claimed Castro survived 630+ assassination attempts

Bay of Pigs Invasion (First Major Attempt)

• CIA proposed elimination plan to Presidents Eisenhower & Kennedy
• Kennedy wanted to humble Cuba as major presidential achievement
• US cut diplomatic ties with Cuba, launched Bay of Pigs invasion
• Mass Cuban emigration following 1959 revolution due to political repression
• Brigade 2506: 1,400-man CIA-trained Cuban exile force
• CIA used disguised American B-26 bombers as Cuban Air Force planes
• Invasion failed, defeated by Cuban armed forces

Poisoned Cigar Plot (1960)

• CIA targeted Castro's smoking habit (smoking since age 14)
• August 16, 1960: CIA Office of Medical Services received box of Castro's preferred cigars
• Cigars treated with botulinum toxin (most poisonous biological substance)
• Would cause muscle paralysis & death upon mouth contact
• Poisoned cigar never reached Castro
• Urban legend of explosive cigar plot in NYC during UN visit (less evidence)
• Castro quit smoking in 1985

Conventional Assassination Squads

• Robert Maheu (attorney, former Howard Hughes aide) acted as CIA intermediary
• Organized 5 conventional assassination squads after Bay of Pigs failure
• Team leader: John "Handsome Johnny" Roselli (mobbed-up gambler)
• Worked with James O'Connell & William King Harvey ("America's James Bond")
• Built Ocean's Eleven-style assassination teams
• Plans included grenade attack during sports game
• Fifth group arrested in early 1963 establishing sniper roost in Havana
• Irony: Kennedy assassinated by sniper later in 1963, Castro survived

Mafia Collaboration (Operation "Family Jewels")

• CIA partnered with Mafia due to shared anti-Castro interests
• Castro's regime eliminated Mafia financial interests in Havana
• Roselli contacted Santos Trafficante & Momo Salvatore "Sam Gold" Giancana (FBI Most Wanted)
• Plan: poison Castro's food/drink with botulinum toxin
• Juan Orta recruited as Cuban official with Castro access
• Orta received botulinum toxin pills, failed multiple times, backed out
• Second attempt: Tony Varona with thousands of dollars
• Target: Castro's chocolate milkshake at frequented Havana restaurant
• Poison passed to restaurant worker, attempt failed due to nervousness
• Conflicting reports: poison frozen in freezer coils or capsule broken on shelf

Scuba Diving Assassination Attempts

• CIA aware of Castro's scuba diving hobby
• 1963: Desmond Fitzgerald (CIA anti-Castro Task Force head) planned explosive seashell
• Rigged seashell to be placed in Caribbean diving area
• Would explode when Castro picked it up underwater
• Plan impractical: relied on chance, couldn't find shell large enough for sufficient explosives
• Wetsuit poisoning plan involving James Donovan (Bay of Pigs prisoner negotiator)
• CIA purchased diving wetsuit, coated with Madura's foot fungus
• Breathing apparatus infected with tuberculosis bacilli
• Contaminated suit never left CIA laboratory, clean suit given to Castro

Marita Lorenz Assassination Plot

• German-American woman, mother worked for OSS/CIA/Pentagon
• Father operated cruise ship line
• Met Castro February 1959 aboard MS Berlin in Havana harbor
• Long tumultuous affair, Castro flew her to Havana on private jet
• Became pregnant, Castro wanted nothing to do with child
• Drugged by Castro's aide, woke up in hospital, pregnancy terminated
• Recruited by CIA-backed anti-communist groups in Miami
• Trained for weeks to dose Castro with botulinum toxin pills
• Winter 1960: returned to Cuba under guise of personal matters
• Mission: slip pills into Castro's drink (death within 1 minute)
• Felt conflicted upon arrival, pills melted in face cream jar
• Met Castro in hotel room before his speech
• Confessed assassination intention to Castro
• Castro produced pistol, handed it to Marita offering her chance to shoot him
• Marita unloaded pistol, Castro replied: "You can't kill me. Nobody can kill me."
• Encounter ended in intimate reunion

Reputation Assassination Attempts

• 1960: Plan to spray aerosolized LSD into radio station during Castro's address
• Goal: make Castro sound insane, reduce credibility
• Thallium salts plot to remove Castro's iconic beard
• Chemical dusted on shoes would cause loss of beard, eyebrows, pubic hair
• Neither plan executed

Presidential Timeline of Attempts

• Eisenhower & Kennedy: initial attempts
• Lyndon B. Johnson: continued assassination attempts
• Richard Nixon: highest number of attempts (184 total)
• Gerald Ford: signed executive order ending official assassination attempts
• 2000: Panama speech plot with 200 pounds of explosives under podium
• Four-man team led by CIA operative Luis Posada intercepted & arrested
• Team later pardoned, relocated to Florida

Castro's Survival & Security

• Reputation for being "seemingly immortal" until death in 2016
• Survival due to competent security team & CIA incompetence
• Constantly moving with cadre of body doubles
• Unlike modern dictators, didn't let assassination attempts limit daily activities
• When asked about bulletproof vest: "I have a moral vest"