THE CHICAGO PLOT: THE FORGOTTEN ATTEMPT ON JFK

By Joe Marzo

The cold November wind whipped through the concrete canyons of downtown Chicago. It was 1963—just weeks before America would be shattered by a rifle shot in Dealey Plaza—but something ominous was already brewing in the Windy City. President John F. Kennedy, young, charismatic, and increasingly controversial, was scheduled to visit on Saturday,

November 2, for a football game at Soldier Field and to deliver a key political speech in preparation for his re-election campaign. But the streets he would never drive through that day had already been marked for violence.

A Tip from the Underground

Just days before JFK’s scheduled arrival, Chicago’s law enforcement and intelligence network began to buzz with anxiety. A confidential FBI informant embedded in a local anti-Castro group had come forward. His warning was specific and urgent: four men—two of them Cuban nationals—had arrived in Chicago with plans to assassinate the president.

According to the tip, the men had acquired rifles with scopes and were reportedly planning to ambush the motorcade from a tall building along the motorcade route—somewhere between Jackson Park and the Loop. The group had allegedly rented an apartment overlooking a key section of the route.

The information, detailed and credible, was relayed to the Secret Service and verified by multiple sources, including a motel clerk who had overheard the Cuban men discussing their plan. In a quiet but coordinated scramble, the Chicago Police Department and the Secret Service began surveillance and prepared to act.

A Dangerous Man in the Right Place

The investigation led to a man named Thomas Arthur Vallee—a 30-year-old ex-Marine stationed at a printing plant on the planned route of the presidential motorcade. Vallee, described as unstable and intensely anti-Kennedy, had a troubling history.

He had recently made violent threats against the president and had been under surveillance by local authorities. More troubling was Vallee’s background: a former U.S. Marine with a marksman rating, recently discharged after being diagnosed with paranoid schizophrenia. He had reportedly worked on covert missions in Asia and was known to have expressed support for anti-Castro efforts.

On November 2, just hours before Kennedy was due to arrive, police pulled Vallee over. In his car they found an M1 Garand rifle, a .30-caliber carbine, and over 3,000 rounds of ammunition. A search of his apartment turned up more firearms and radical anti-Kennedy literature. The arsenal alone was enough to give seasoned agents nightmares.

Vallee worked in a building near Jackson and Dearborn—just the kind of vantage point a trained sniper would need to get a clean shot. It’s worth pausing here to consider: this setup was nearly identical to what would unfold in Dallas three weeks later. A lone gunman, high up in a building, a presidential motorcade below, and ties to murky political motives.

Was Dallas a copycat? Or was Chicago the rehearsal?

The Vanishing Men

But Vallee wasn’t the only threat.

The original FBI tip had mentioned four men. Vallee was one. But what of the others? The two Cuban nationals the motel clerk had reported vanished before police could make contact. Despite being linked to an apartment rental near the motorcade route and to radical anti-Castro networks, no official record of their interrogation—or even their names—has ever surfaced.

Were they part of the plot? Were they protected assets? The lack of follow-up, documentation, or public acknowledgment only deepened the mystery. Some researchers believe they were quietly deported or allowed to slip away to prevent embarrassment or international scandal. The U.S. was already entangled in Cold War tensions, the aftershock of the Bay of Pigs disaster, and delicate negotiations with Cuba and the USSR. The last thing the Kennedy administration needed was a public spectacle tied to Cuban exiles.

The Sudden Cancellation

On November 2, President Kennedy was supposed to leave Washington for Chicago. The Secret Service, now aware of the threat, strongly urged cancellation. At the last minute, the trip was officially called off. The public was told Kennedy had a cold. Behind the scenes, the decision was made to abort the motorcade—and in doing so, potentially save his life.

There was no press conference. No announcement about the plot. No arrests of Cuban suspects. It all vanished into a quiet internal report. It would take decades for even fragments of this story to surface.

The timing was haunting. Just 20 days later, Kennedy would ride in another open motorcade through another city. But this time, there would be no last-minute warning, no canceled trip, no hidden guns intercepted. The shots in Dallas would echo through history.

Abraham Bolden and the Silencing of Truth

One man tried to tell the story.

Abraham Bolden, the first Black Secret Service agent assigned to a presidential detail, was working in Chicago when the attempt on JFK’s life was foiled. Bolden would later testify that the Chicago plot was very real—and that the government deliberately covered it up.

When Bolden began speaking out about the negligence and misconduct he observed within the Secret Service—including heavy drinking on the job and lax procedures—he was arrested in 1964 for allegedly attempting to sell government secrets. The trial was marred by witness recantations and prosecutorial misconduct, but Bolden was convicted and imprisoned for six years.

He maintained until his death that his imprisonment was retaliation for blowing the whistle—and that the Chicago plot was directly connected to what later happened in Dallas.

A Shadow of the Future

The similarities between the Chicago and Dallas plots are striking:

• Both featured former Marines with intelligence connections (Vallee and Oswald).

• Both had sniper nests along the motorcade route in tall buildings.

• Both suspects were tied to volatile political movements (anti-Castro and pro-Cuba).

• Both plots involved last-minute warnings ignored or suppressed.

• Both plots were initially treated as the work of “lone nuts.”

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Some researchers believe Chicago was a test run—a dry rehearsal to evaluate security weaknesses and refine the operation that succeeded in Dallas. Others argue it was an entirely separate but no less dangerous attempt on the life of the president.

Whatever the truth, one thing is clear: the American public was never told. The assassination attempt in Chicago was buried, redacted, and forgotten. Until now.

Sources

• Bolden, Abraham. The Echo From Dealey Plaza. Random House, 2008.

• Douglass, James W. JFK and the Unspeakable: Why He Died and Why It Matters. Orbis Books, 2008.

• Talbot, David. Brothers: The Hidden History of the Kennedy Years. Simon & Schuster, 2007.

• Morley, Jefferson. The Ghost: The Secret Life of CIA Spymaster James Jesus Angleton. St. Martin’s Press, 2017.

• United States National Archives. JFK Assassination Records Collection.

• Church Committee Reports, Book V: The Investigation of the Assassination of President John F. Kennedy: Performance of the Intelligence Agencies. 1976.

• Chicago Tribune Archives, Nov. 1963 (reconstructed from FOIA-released material).

• Interviews with Bolden in The Men Who Killed Kennedy (Documentary Series, History Channel).