Death of the American Dream: Terrence McCauley on why the Mob was behind the JFK Assassination episode artwork

EPISODE · Jul 2, 2025 · 38 MIN

Death of the American Dream: Terrence McCauley on why the Mob was behind the JFK Assassination

from Keen On America · host Andrew Keen

If the American dream died in Dealey Plaza on November 22, 1963, then who killed it? According to the crime novelist Terrence McCauley, the JFK assassination was carried out by organized crime. That’s the heart of his new novel, Twilight Town, in which McCauley reexamines the JFK assassination in Dallas. But this wasn't Oliver Stone style CIA or shadowy government conspirators, pulling well-oiled strings from their deep state offices. Instead, McCauley argues it was something far more mundane yet chilling: a street-level contract hit executed by mob-connected criminals with intelligence ties. These were the same underworld figures who ran guns to Cuba, operated training camps for Bay of Pigs veterans, and had both the means and motive to eliminate a President they saw as soft on communism and hard on organized crime. In McCauley's vision, America's Camelot ended not through some grand operatic conspiracy, but through the banal efficiency of professional killers.1. The JFK Assassination Was a "Street Crime," Not a High-Level Government Plot "I approach it as the way I thought it was. And that is a contract hit and a street crime, which is ultimately what happened on the streets of Dallas that morning." McCauley argues the assassination was carried out by mob-connected criminals with intelligence ties, not CIA masterminds in smoke-filled rooms.2. Only a Small Group Knew the Full Plan "I think maybe 10 or 20 at the most who knew all the details and much fewer than that who knew exactly what was going to happen and when." McCauley believes the conspiracy was deliberately kept small, citing FBI recordings of Joseph Milteer who said such operations only work with minimal participants.3. Lee Harvey Oswald Didn't Pull the Trigger "I never was able to put a gun in Oswald's hands that day... I don't think he did. No, I think he was involved with the people who did." McCauley argues Oswald was connected to the plotters but wasn't the actual shooter, pointing to inconclusive gunpowder residue tests.4. The Assassination Marked "The End of American Innocence" "It was certainly the end of American innocence, where we thought we were always the good guys, where we were the liberators, and where we were one hope of the world against the ongoing threat of communism." McCauley sees November 22, 1963, as the moment America lost its post-WWII optimism.5. The Cover-Up Happened Because Intelligence Agencies Recognized Their Own Assets "The coverup happened because these organizations looked into it. They realized, well, so-and-so could have this off, and we worked with them for 10 years, let's back away from that." McCauley suggests the cover-up wasn't planned but emerged when agencies discovered their own connected operatives were involved.The American Dream has more lives than cats. It was supposed to have died in November 1963 in Dallas, then in 1968 with the assassinations of MLK and RFK, then in the Fall of Saigon, then at the Watergate Building, then at the Twin Towers on 9/11. And then, of course, there is Trump, who is supposed to have slain the American Dream not once but twice. And yet today, a couple of days before Independence Day, my sense is that the Dream is alive all over America. The promise of individual agency continues to inspire new generations of both native and immigrant Americans. JFK might be gone, but the Dream remains the defining quality of the American experience. Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

If the American dream died in Dealey Plaza on November 22, 1963, then who killed it? According to the crime novelist Terrence McCauley, the JFK assassination was carried out by organized crime. That’s the heart of his new novel, Twilight Town, in which McCauley reexamines the JFK assassination in Dallas. But this wasn't Oliver Stone style CIA or shadowy government conspirators, pulling well-oiled strings from their deep state offices. Instead, McCauley argues it was something far more mundane yet chilling: a street-level contract hit executed by mob-connected criminals with intelligence ties. These were the same underworld figures who ran guns to Cuba, operated training camps for Bay of Pigs veterans, and had both the means and motive to eliminate a President they saw as soft on communism and hard on organized crime. In McCauley's vision, America's Camelot ended not through some grand operatic conspiracy, but through the banal efficiency of professional killers.1. The JFK Assassination Was a "Street Crime," Not a High-Level Government Plot "I approach it as the way I thought it was. And that is a contract hit and a street crime, which is ultimately what happened on the streets of Dallas that morning." McCauley argues the assassination was carried out by mob-connected criminals with intelligence ties, not CIA masterminds in smoke-filled rooms.2. Only a Small Group Knew the Full Plan "I think maybe 10 or 20 at the most who knew all the details and much fewer than that who knew exactly what was going to happen and when." McCauley believes the conspiracy was deliberately kept small, citing FBI recordings of Joseph Milteer who said such operations only work with minimal participants.3. Lee Harvey Oswald Didn't Pull the Trigger "I never was able to put a gun in Oswald's hands that day... I don't think he did. No, I think he was involved with the people who did." McCauley argues Oswald was connected to the plotters but wasn't the actual shooter, pointing to inconclusive gunpowder residue tests.4. The Assassination Marked "The End of American Innocence" "It was certainly the end of American innocence, where we thought we were always the good guys, where we were the liberators, and where we were one hope of the world against the ongoing threat of communism." McCauley sees November 22, 1963, as the moment America lost its post-WWII optimism.5. The Cover-Up Happened Because Intelligence Agencies Recognized Their Own Assets "The coverup happened because these organizations looked into it. They realized, well, so-and-so could have this off, and we worked with them for 10 years, let's back away from that." McCauley suggests the cover-up wasn't planned but emerged when agencies discovered their own connected operatives were involved.The American Dream has more lives than cats. It was supposed to have died in November 1963 in Dallas, then in 1968 with the assassinations of MLK and RFK, then in the Fall of Saigon, then at the Watergate Building, then at the Twin Towers on 9/11. And then, of course, there is Trump, who is supposed to have slain the American Dream not once but twice. And yet today, a couple of days before Independence Day, my sense is that the Dream is alive all over America. The promise of individual agency continues to inspire new generations of both native and immigrant Americans. JFK might be gone, but the Dream remains the defining quality of the American experience. Keen On America is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit keenon.substack.com/subscribe

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If the American dream died in Dealey Plaza on November 22, 1963, then who killed it? According to the crime novelist Terrence McCauley, the JFK assassination was carried out by organized crime. That’s the heart of his new novel, Twilight Town, in...

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