signup now
How the Outfit Killed JFK
  • November 21, 2011 : 20:11
  • comments

For most Chicago mobsters, muscular Charles Nicoletti—nearly six feet tall and with a lantern jaw—could be a frightening sight. Nevertheless, he defied the stereotypes of a mob killer. On most days he wore a suit and tie. His hangouts included insurance agencies, car dealerships and a company that made burial vaults.

Despite the businessman trappings, Nicoletti was the son of an abusive father, whom he killed at the age of 12 after the man beat his mother. The Outfit became his family, and Nicoletti worked his way up the ranks by dealing dope and making book, for which he was repeatedly arrested and jailed. Inside the mob, Nicoletti’s intelligence and heartlessness made him effective as an enforcer. Charles Crimaldi, another hit man who had turned informant, called Nicoletti “the most respected and the most dangerous” man in the Outfit, adding, “He don’t want to impress anybody. He just wants to go about his business.”

By the early 1960s police believed Nicoletti was the Outfit’s third-ranked leader and right-hand man to Giancana. At this stage Nicoletti’s skills were reserved for only the most sensitive contracts, and when he went out with another hit man, Files claimed to be the third man behind the wheel.

Despite Nicoletti’s fearsome reputation, Files called him “Mr. Nicoletti” and said he was the closest thing to a father figure he ever had.

During his discussions with Irvin, Files gave vivid accounts of the weeks leading up to the assassination. Then 21, he was playing pinball at his favorite hangout when Nicoletti first told him that Giancana had put out a contract on “your friend”—the president. Nicoletti instructed Files to acquire the weapons and bring them to Texas in the hidden trunk compartment of a 1963 Chevrolet, a “work” car that couldn’t be traced.

Files told Irvin the following story about his journey to Dallas: He stayed in a courtyard motel on the western outskirts of Dallas and met Lee Harvey Oswald, who took him downtown to point out the best escape routes from the city. Oswald also took him to an abandoned field, where Files test-fired guns hidden in the trunk. (Oswald, he said, didn’t want to shoot.) Upon their return to the motel Oswald took a picture of him standing shirtless next to his portable record player—a photo Files kept but one that would have been more telling had it included the photographer.

Files claimed he made contact with another Outfit leader on November 21. Early that morning he drove to the swanky Cabana Motor Hotel in Dallas, where he picked up Johnny Roselli. Then 58, Roselli had carefully cut silver hair and wore tinted glasses and silk suits. He was every bit the flashy mob kingpin Nicoletti was not, but back in his younger Chicago days Roselli was equally feared as a hit man. By 1963 he was hanging out at the Friars Club in Los Angeles with his pal Frank Sinatra and was caught a few years later in an elaborate card-cheating scheme. It brought him a brief prison sentence and a permanent ban from Las Vegas casinos. In Dallas, Files said, he took Roselli to a pancake house, where he met Jack Ruby.

According to Files, Nicoletti did not join him until the morning of November 22. The two went to Dealey Plaza, using as a guide a map of the motorcade route that Roselli had gotten from Ruby. He and Nicoletti picked a spot in the Dal-Tex tower (next to the Texas School Book Depository, where Oswald worked) for Nicoletti to shoot from. Only then, Files says, did the hit man ask him to be a backup. Nicoletti feared Roselli was too rusty to hit a target from a long distance, and he knew Files had been trained as a sniper in the Army. Files said he set up behind the stockade fence on the grassy knoll to get a shot from the front of the procession. The weapon he chose was a Remington Fireball, a cross between a rifle and a pistol that could fit inside an attaché case. Nicoletti’s one instruction was not to hit Jackie. Files followed the motorcade through the scope of his Remington and shot a .222 caliber bullet that hit the president in the right temple. He then casually took off his jacket, turned it inside out and put his gun back in its case.

During his brief encounter with Oswald, Files said, the two did not discuss each other’s mission. He believed Oswald never fired a shot and was unwittingly there as a patsy—as Oswald himself said after his arrest. Other hit men were in town to kill Oswald, but he slipped away before they got to him—the major glitch in the day’s operation.

For Irvin, James Files was the missing link to the real conspiracy behind the JFK assassination. Irvin wanted Shelton to interview Files to make sure he didn’t turn out to be as flaky as West’s previous sources.

“I thought some of what Files said was a little too good to be true,” Shelton admits. “That was my first impression. But I thought there was a ring of truth to it, too. Nicoletti was the perfect person for the Outfit to send. I could understand why it wanted Roselli in Dallas too, because they trusted him to operate things. But at that stage of his life Roselli couldn’t have been a shooter. It made sense that Nicoletti would have wanted someone else to back him up.”

But nothing about the Files story was more compelling for Shelton than the fates of the three central Outfit characters: All of them had been killed in the mid-1970s after being summoned by congressional committees: Giancana and Roselli around the time of a Senate investigation and Nicoletti just a day after one of Blakey’s investigators called looking for him. All had ranked high enough in the mob’s hierarchy to have directly implicated Accardo and Aiuppa in a conspiracy to kill the president. Was Accardo covering his tracks?

Shelton’s efforts to interview Files in 1993 were leaked to the press by one of Irvin’s associates, and the FBI wouldn’t allow it. The bureau instead sent two other agents to interview the Illinois prisoner, and they deemed his information unworthy of further investigation. Shelton watched from the sidelines as TV impresario Dick Clark produced a show for NBC based on Files’s confession. At the last minute the network brought in consultants who declared Files a fraud, and the program was scrubbed.

Shelton still wouldn’t let go of the Files story. Although he realized it had many holes, he says, “There was just too much detail for him to have made everything up.” After he retired from the FBI in 1998 and opened his own private investigation firm, he approached Clark about getting the Files story back on the air. “Dick Clark had me out to his office,” Shelton recalls, “and I think he believed there was something to pursue, but he had just been burned too badly to try again.” Meanwhile, Joe West’s organization had splintered. Some of the pieces had been picked up by a Dutch investor, Wim Dankbaar, who offered to cover Shelton’s expenses if he could corroborate Files’s claims. (Dankbaar used some of Shelton’s research in his book and video, Files on JFK.)

For Shelton that collaboration came with the discovery of two men who claimed independently that they had helped bring the hit men to Dallas. Chauncey Marvin Holt said he drove Nicoletti from a ranch in Arizona, and William Robert Plumlee said he flew Roselli into town the day before the assassination. Each man had spent a significant part of his life on the Gulf Coast, and each had connections to the mob, the CIA and Cuba.

According to an extensive FBI file, Plumlee claimed he made his first clandestine flights to Cuba in support of Castro, supplying guns mobsters had stolen from a National Guard armory. He served time for passing a bad check but was still used as a contract pilot by the CIA, helping to equip such right-wing guerrilla groups as Oliver North’s Contras. Plumlee claimed his CIA contacts had ordered him to fly Roselli to Dallas the day before the assassination.

The CIA connection with Roselli was not farfetched. It is now known that in 1960 the CIA approached Roselli through a Las Vegas hotel executive (and former FBI agent) to assist in a plan to assassinate Castro. Roselli introduced the go-between to Giancana and Tampa mob boss Santo Trafficante Jr., who had casinos expropriated by Castro and was briefly jailed in Cuba after the revolution. The CIA supplied poison that a Trafficante confederate was supposed to slip into Castro’s food, but nothing came of the effort.

Roselli testified about the escapade when it was revealed in 1975 during the hearings into Alleged Assassination Plots Involving Foreign Leaders led by Idaho senator Frank Church. But Roselli may have talked too freely. He disappeared within weeks of his third appearance before the committee, in 1976. His body was found sawed in half and stuffed inside an oil drum floating off Biscayne Bay. His death so rattled Plumlee that he contacted local FBI agents to inform them of his role in bringing Roselli to Dallas, but he claimed the effort was to “abort” the assassination, not assist it.

  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
read more: News, politics


  • Anonymous
    Where is Tosh Plumlee today? It seems old man history now supports Plumlee's story and background. He appears to be a very deep operative over a very long period of time.
  • Anonymous
    Most Overlooked Fact: During Jim Garrison's trial of Clay Shaw an Appellate Court panel threw out ,as inadmissible evidence, the Warren Commission Report due to it being FICTION.The only time Commission Report faced legal scrutiny.
  • Anonymous
    The Plumlee CIA connection. Yes. It does appears Plumlee is a CIA central character; Cuba, Kennedy, Contra and beyond. WOW!
  • Anonymous
    During Clay Shaw's trial an appellate panel ruled the Warren Commission Report "inadmissible" as evidence due to it being fiction.The only time it was subjected to legal or judicial scrutiny. Ray Guiducci-Most Overlooked Fact, July 20,2012.