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JFK The Enduring Secret · Friday · 32 min

Episode 347 Jack Ruby Miniseries Part 23

In this twenty-third installment of our Jack Ruby miniseries, we revisit Jack Ruby’s infamous summer 1959 trip to Cuba and unravel the paper trail that shatters sixty years of official cover stories. For decades, the Warren Commission portrayed Ruby's presence in Havana as an innocent, week-long vacation, backed by a single postcard sent to his girlfriend Alice Nichols from the FOCSA building. However, official Cuban immigration tourist cards and federal archives expose a massive physical contradiction: while his immigration card registered a continuous 34-day stay from August 8 to September 11, 1959, Dallas bank deposit logs and FBI contact reports place him physically in Texas on three separate dates during that exact window. Forensic handwriting analysis confirmed Ruby personally signed these tourist cards, proving he was not taking a simple holiday, but executing a series of rapid, clandestine flights back and forth across the Straits of Florida. We examine the covert mechanics of Ruby’s Cuban operations, beginning with the sworn account of car rental agent Elaine Minier. Minier revealed that before her own trip to Havana, Ruby met her in Dallas and instructed her to deliver a written, coded message to casino boss Lewis McWillie on the Tropicana floor, declaring that "Sparky from Chicago is coming." We reconstruct the findings of the House Select Committee on Assassinations, which established at least three separate trips in August and September 1959—including a 24-hour turnaround flight between Miami, Havana, and New Orleans—and trace eyewitness testimonies from Chicago tourists who met Ruby at the Tropicana over Labor Day weekend. Furthermore, we investigate the ten-day overlap when Ruby was in Havana while mob boss Santo Trafficante Jr. was held at the minimum-security Trescornia detention camp, examining British journalist John Wilson Hudson's report that Ruby visited Trafficante with food and supplies, alongside McWillie's evasive, shifting under-oath admissions about visiting the camp with Ruby. Finally, we confront Ruby’s mysterious arms trafficking ventures and his repeated visits to Ray’s Hardware in Dallas. We detail the uninvestigated claims of Texas gunrunner Robert Ray McKeown, who testified that Ruby visited his Houston drive-in seeking a letter of introduction to Fidel Castro in exchange for surplus Jeeps in Shreveport and slot machines in New Mexico, while offering thousands in cash to secure the release of detained associates in Cuba. We trace Ruby's history of acquiring firearms—from his failed attempt to ship a .38 Smith & Wesson Centennial revolver COD to McWillie in Las Vegas to his January 1960 purchase at Ray's Hardware, where he walked in alongside a Dallas police officer and a prizefighter to buy the blue steel .38 Colt Cobra snub nose (serial number 2744LW). This very weapon, bought in the company of Dallas law enforcement, would ultimately become the instrument used to execute Lee Harvey Oswald in the City Hall basement.

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In this  twenty-third installment of our Jack Ruby miniseries, we revisit Jack Ruby’s infamous summer 1959 trip to Cuba and unravel the paper trail that shatters sixty years of official cover stories. For decades, the Warren Commission portrayed Ruby's presence in Havana as an innocent, week-long vacation, backed by a single postcard sent to his girlfriend Alice Nichols from the FOCSA  building. However, official Cuban immigration tourist cards and federal archives expose a massive physical contradiction: while his immigration card registered a continuous 34-day stay from August 8 to September 11, 1959, Dallas bank deposit logs and FBI contact reports place him physically in Texas on three  separate dates during that exact window. Forensic handwriting analysis confirmed Ruby personally signed these tourist cards, proving he was not taking a simple holiday, but executing a series of rapid, clandestine flights back and forth across the Straits of Florida.

We examine the covert mechanics of Ruby’s Cuban operations, beginning with the sworn account of car rental agent Elaine Minier. Minier revealed that before her own trip to Havana, Ruby met her in Dallas and instructed her to deliver a written, coded message to casino boss Lewis McWillie on the Tropicana floor, declaring that "Sparky from Chicago is coming." We reconstruct the findings of the House Select Committee on Assassinations, which established at least three separate trips in August and September 1959—including a 24-hour turnaround flight between Miami, Havana, and New Orleans—and trace eyewitness testimonies from Chicago tourists who met Ruby at the Tropicana over Labor Day weekend. Furthermore, we investigate the ten-day overlap when Ruby was in Havana while mob boss Santo Trafficante Jr. was held at the minimum-security Trescornia detention camp, examining British journalist John Wilson Hudson's report that Ruby visited Trafficante with food and supplies, alongside McWillie's evasive, shifting under-oath admissions about visiting the camp with Ruby.

Finally, we confront Ruby’s mysterious arms trafficking ventures and his repeated visits to Ray’s Hardware in Dallas. We detail the uninvestigated claims of Texas gunrunner Robert Ray McKeown, who testified that Ruby visited his Houston drive-in seeking a letter of introduction to Fidel Castro in exchange for surplus Jeeps in Shreveport and slot machines in New Mexico, while offering thousands in cash to secure the release of detained associates in Cuba. We trace Ruby's history of acquiring firearms—from his failed attempt to ship a .38 Smith & Wesson Centennial revolver COD to McWillie in Las Vegas to his January 1960 purchase at Ray's Hardware, where he walked in alongside a Dallas police officer and a prizefighter to buy the blue steel .38 Colt Cobra snub nose (serial number 2744LW). This very weapon, bought in the company of Dallas law enforcement, would ultimately become the instrument used to execute Lee Harvey Oswald in the City Hall basement.

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