The assassination of President John F. Kennedy has remained one of the most controversial and disputed events in American history for more than six decades. Despite the official conclusion of the Warren Commission that Lee Harvey Oswald acted alone, countless alternative theories, investigations, and alleged confessions have emerged over the years, each claiming to reveal a hidden truth. Among the most provocative of these is the story of James E. Files — a convicted criminal who, from behind prison walls, claimed to have been one of the shooters in Dealey Plaza.

The saga begins in 1989, when Houston-based private investigator Joe West, frustrated by what he believed to be a government cover-up, launched his own independent inquiry into JFK’s murder. Over three years, West poured his personal fortune into the investigation, chasing leads that repeatedly ended in dead ends. His persistence, however, eventually paid off in an unexpected way. An anonymous FBI agent contacted him with a tip that pointed toward Joliet State Penitentiary in Illinois and a prisoner named James E. Files, who was serving a 50-year sentence for shooting a police officer.

At first, Files refused to speak. But West, determined and patient, spent months visiting him, writing letters, and slowly building trust. Over time, Files began to open up, gradually revealing what he claimed was his involvement in the assassination. Before West could secure a full confession, however, he fell ill and died in 1993. His work did not end with him. Thirteen months later, on March 22, 1994, West’s associates recorded a videotaped interview with Files that would shock many who later watched it.

In that interview, Files admitted that he was present in Dealey Plaza on November 22, 1963, and that he fired a shot at President Kennedy. He implicated high-ranking organized crime figures — Charles “Chuck” Nicoletti, Johnny Roselli, and Sam Giancana — as key conspirators who orchestrated the plot. According to Files, his role was that of a backup shooter positioned on the grassy knoll, armed with a rare Remington XP-100 “Fireball” single-shot pistol fitted with a scope.

Files described arriving in Dallas a week before the assassination, transporting weapons, and coordinating with Lee Harvey Oswald, whom he claimed was tasked with helping him familiarize himself with escape routes and the layout of the city. He maintained that Oswald knew he was there but was not directly involved in planning or executing the shooting. Files insisted that Oswald did not fire any shots that day, portraying him instead as a patsy set up to take the blame.

On the morning of November 22, Files said he picked up Johnny Roselli, met Jack Ruby at a Fort Worth pancake house to obtain Secret Service identification and a motorcade route map, and later scouted Dealey Plaza with Nicoletti. He claimed Nicoletti positioned himself inside the Dal-Tex Building, while Files chose a spot behind a fence on the grassy knoll overlooking Elm Street.

According to Files, the plan was to ensure Kennedy’s death while avoiding harm to Jacqueline Kennedy. He stated that he fired only when he believed it was his last clear shot, timing it almost simultaneously with Nicoletti’s. He described in graphic detail watching the fatal headshot, returning his weapon to a briefcase, disguising himself by turning his jacket inside out, and calmly walking away through the railroad yard.

Perhaps most chillingly, Files claimed he placed his fired shell casing on top of a fence, biting it beforehand to leave distinctive teeth marks — a supposed “calling card.” Years later, forensic examiners reportedly found such marks on a casing recovered from the area, though its connection to Files remains disputed.

Files also recounted how he was paid $30,000 in cash for his role, delivered in an envelope by Nicoletti weeks after the assassination. He admitted initially lying about the amount but later clarified the full sum during the interview.

Beyond his own actions, Files painted a broader picture of a conspiracy involving organized crime and elements of U.S. intelligence. He claimed to have worked with CIA operative David Atlee Phillips in training Cuban exiles prior to the Bay of Pigs invasion, which he cited as his personal motivation for hating Kennedy. He suggested that the CIA provided Secret Service IDs used by conspirators that day, though he stopped short of directly accusing the agency of ordering the hit.

Files further alleged that Lee Harvey Oswald was under the same CIA controller as him, implying Oswald had been manipulated rather than acting independently. He maintained that Oswald’s role was to mislead investigators by planting evidence, not to kill the president.

The interview also delved into the mysterious deaths of key mob figures tied to the case. Sam Giancana was murdered in 1975 just days before he was scheduled to testify before the Senate Select Committee on Intelligence. Johnny Roselli was killed in 1976, his body discovered in an oil drum in Miami. Charles Nicoletti was assassinated in 1977 shortly after being named as a potential witness in congressional hearings. The House Select Committee on Assassinations later concluded in 1979 that Kennedy was “probably” killed as the result of a conspiracy — though it did not name Files or definitively identify other shooters.

Files claimed that shortly before Nicoletti’s death, Nicoletti gave him a package containing Secret Service IDs, a personal diary detailing killings, and the original motorcade map — materials Files said he buried, later recovered after being abducted and tortured by unknown agents, and partially destroyed.

Despite the dramatic nature of his account, the FBI has officially dismissed Files’ confession as non-credible, citing inconsistencies and lack of verifiable evidence. Nonetheless, his testimony continues to fuel debate among researchers, conspiracy theorists, and historians who argue that the official narrative remains incomplete.

Files himself expressed little remorse in the interview, stating that at the time, he believed Kennedy deserved to die due to the betrayal of Cuban exiles during the Bay of Pigs. He described death as “just another adventure” and insisted he would follow orders again if placed in the same situation.

Even now, Files remains incarcerated in Joliet, still serving what amounts to a life sentence. Whether he is a confessor of truth, a manipulator seeking attention, or a man weaving fiction from fragments of reality remains unresolved.

What his story undeniably does is reopen uncomfortable questions about power, secrecy, and accountability in American history. If even a fraction of what Files described is true, then the assassination of JFK was not merely a tragedy — it was a coordinated operation that reshaped the nation’s destiny from the shadows.

More than sixty years later, Dealey Plaza remains haunted not just by gunfire, but by unanswered questions that refuse to fade. The story of James E. Files may never be fully proven or disproven, but it stands as a stark reminder that history is often far messier — and far darker — than the official version suggests.