Jack 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.