Jack Caulfield was born in New York on 12th March 1929. His parents were Irish immigrants and hoped that he would become a priest. According to one report, Caulfield was "an avid basketball player in a part of town that didn't have a net, he practiced by shooting the ball through the rungs of the fire-escape ladders on the tenement buildings". Caulfield won a basketball scholarship to Wake Forest University. This was followed by two years in the United States Army during the Korean War.
On 1st June, 1953, Caulfield joined the New York City Police Department. Caulfield spoke fluent Spanish and therefore two years later he was transferred to the NYPD's Bureau of Special Service and Investigation (BOSSI). His assignments included escorting and guarding the security of world leaders and their families. People who Caulfield protected included Fidel Castro, Che Guevara, Richard Nixon and Nikita Khrushchev.
Caulfield also investigated political groups including the American Nazi Party, the Fair Play For Cuba Committee (FPCC) and a terrorist group based in Canada. Douglas Martin has pointed out: "Having risen from foot patrol to detective in two years in the New York Police Department, he became part of an elite unit that protected visiting dignitaries and gathered intelligence information."
According to Caulfield: "My multi-faceted, twelve-year BOSSI experience convinced me in late 1967 that Richard Nixon was going to run and likely win the Presidential election in 1968. I subsequently approached the Nixon people from the 1960 Presidential campaign (with whom I had worked as a BOSSI detective) and made it known I was available for candidate/staff security purposes during the 1968 campaign." After being interviewed by H. R. Haldeman and Rose Mary Woods he was appointed as Chief of Security for the Nixon Campaign Staff.
Richard Nixon defeated Hubert Humphrey in the 1968 presidential election and in April, 1969, Caulfield was appointed as Staff Assistant to the President. Soon afterwards Nixon decided that the White House should establish an in-house investigative capability that could be used to obtain sensitive political information. After consulting John Ehrlichman and H. R. Haldeman the job was given to Caulfield.
Caulfield now appointed an old friend, Tony Ulasewicz, to carry out this investigative work. Ulasewicz's first task was to investigate the links between Bobby Baker and leading Democratic Party politicians. He was also ordered by Caulfield to set up a round-the-clock surveillance of Edward Kennedy. Over the next three years Ulasewicz traveled to 23 states gathering information about Nixon's political opponents. This included people such as Edmund Muskie, Larry O'Brien, Howard Hughes and Jack Anderson.
On 19th July, 1969, Tony Ulasewicz received a phone call from Caulfield: "Get out to Martha's Vineyard as fast as you can, Tony. Kennedy's car ran off a bridge last night. There was a girl in it. She's dead." This phone call took place less than two hours after the body of Mary Jo Kopechne, the former secretary of Robert Kennedy, had been found in a car that Caulfield suspected Edward Kennedy had been driving.
Ulasewicz was one of the first to arrive in Chappaquiddick after the tragedy. In several cases he was able to interview several key witnesses. This included Sylvia Malm who was staying in Dike House at the time. Dike House was only 150 yards from the scene of the accident. Malm told Ulasewicz that she was reading in bed on the night of the accident. She remained awake until midnight but no one knocked on her door.
Tony Ulasewicz also discovered that the request for an autopsy by Edmund Dinis, the District Attorney of Suffolk County, had been denied. Dinis was told that the body had already been sent to Kopechne's family. This was untrue, the body was still in Edgartown. Ulasewicz also interviewed John Farrar, the scuba diver who pulled Mary Jo Kopechne out of Kennedy's car. Farrar told Ulasewicz that the evidence he saw suggested that she had been trapped alive for several hours inside Kennedy's car.
He also discovered that the "records of Edward Kennedy's telephone calls in the hours after the accident at Chappaquiddick were withheld by the telephone company from an inquest into the death of Mary Jo Kopechne without the knowledge of the Assistant District Attorney who asked for them". He leaked this information to various newspapers but it was only taken up by the Union Leader of Manchester, New Hampshire. It was not until 12th March, 1980, that the New York Times published the story.
Caulfield was involved in at least two attempts to carry out illegal electronic surveillance on people Richard Nixon. considered could do him political harm. The first occasion was in June 1969, when Caulfield was employed by John Ehrlichman to place a wiretap on the telephone of newspaper writer, Joseph Kraft. Caulfield employed former FBI agent, Jack Ragan, to carry out this task. The following year he involved in the electronic surveillance Nixon's nephew, F. Donald Nixon.
Caulfield was also engaged in multi-subject White House liaison activities. This involved working with Federal Bureau of Investigation, Central Intelligence Agency, Interpol, and the National Association of Chiefs of Police, on subjects such as cross-border narcotics trafficking and monitoring violent anti-war demonstrations.
On 17th September, 1971, John Dean and Jeb Magruder asked Caulfield to establish a new private security firm. Caulfield was told that Tony Ulasewicz and his associates would be required to carry out "surveillance of Democratic primaries, convention, meetings, etc.," and collecting "derogatory information, investigative capability, worldwide." Caulfield was told that this was an "extreme clandestine" operation. Given the name Operation Sandwedge, its main purpose was to carry out illegal electronic surveillance on the political opponents of Richard Nixon.
Charles Colson suggested to Caulfield that his men fire-bomb the Brookings Institute (a left-wing public policy group involved in studying government policy in Vietnam). Caulfield sent Ulasewicz to investigate the location of offices, security provisions, etc. According to Caulfield the fire-bomb plan was eventually "squelched" by John Dean.
In April 1972 President Richard Nixon appointed Caulfield as Assistant Director: Criminal Enforcement - Alcohol, Tobacco, and Firearms. Caulfield was placed in charge of over 1,500 Federal agents. John Dean wrote that John Ehrlichman had hoped Caulfield could use the post to "influence how both friends and enemies of the White House were treated by the Internal Revenue Service."
Caulfield did not work for the White House when the Watergate break-in took place. However, John Ehrlichman immediately assumed that it had been part of Operation Sandwedge and that Tony Ulasewicz had been involved. In fact, it was part of Operation Gemstone, another Nixon dirty tricks campaign.
Herbert W. Kalmbach and John Dean decided that Ulasewicz was the best man to deliver the "hush money". He admitted later that he gave Dorothy Hunt a total of $154,000. This was to be passed on to those members of Operation Gemstone who had been arrested and awaiting trial. On 21st December, 1972, James W. McCord wrote a letter to Caulfield. McCord told him he was thinking of making a statement that "would involve allegations against people in the White House and other high administration officials." Caulfield relied: "I have worked with these people and I know them to be as tough-minded as you. Don't underestimate them."
On 30th January, 1973, James W. McCord, Gordon Liddy, Frank Sturgis, E. Howard Hunt, Virgilio Gonzalez, Eugenio Martinez, and Bernard L. Barker were convicted of conspiracy, burglary and wiretapping. However, on 19th March, 1973, McCord wrote a letter to Judge John J. Sirica claiming that the defendants had pleaded guilty under pressure (from John Dean and John N. Mitchell) and that perjury had been committed. McCord also revealed details of how Caulfield and Tony Ulasewicz had been involved in Nixon's dirty tricks campaigns. As a result of this information, Caulfield was forced to resign as Assistant Director of Criminal Enforcement.
Caulfield asked John Sears to become his lawyer. Later, Leonard Garment (In Search of Deep Throat) was to claim that Sears was Deep Throat. Garment believed it was Caulfield who provided Sears with some of the information that was used against those involved in the Watergate conspiracy.
Sam Ervin and the Senate Watergate Committee began on 17th May, 1973. One of the first witnesses to appear was Caulfield who admitted the role that he and Tony Ulasewicz had played in Operation Sandwedge. Ulasewicz appeared before the committee on 23rd May, 1973. To his surprise, the senators did not ask any specific questions of his work for Richard Nixon. Instead they concentrated on how he delivered the money to the Watergate burglars.
In June 1974, Alexander Haig began a classified investigation to determine whether Nixon had received cash contributions from leaders of Southeast Asia and the Far East. Caulfield was interviewed about the possibility that he had collected some of this money from people in Vietnam.
Unlike most of the other figures in the story, Jack Caulfield did not write an account of the Watergate Scandal in the 1970s. However, according to his wife, Nancy Caulfield, her husband spent much of his time in his final years working on his autobiography, Caulfield, Shield #911-NYPD. The book was published in April 2012.