Calabrese père and fils were incarcerated together at a federal penitentiary in Milan, Michigan, for a 1997 loan-sharking conviction when Frank Jr. decided to rat out the old man. In three letters to the FBI's Chicago organized crime section (below and on the following two pages), Frank Jr. offered to wear a wire during "a long in-depth talk" he planned with Frank Sr. as the two strolled the "inside yard." Junior, who regards the older Calabrese as "a sick man," wrote FBI agent Tom Bourgeois that Frank Sr. had agreed to clear the air and had pledged, "We should … hold nothing back." Though Frank Jr. wrote in his third letter to Bourgeois (Page 3) that there would be only "one conversation," apparently the big guy really opened up. The trial exhibits include transcripts and audiotapes of at least three separate father/son sessions. Tapes of a fourth "heart-to-heart talk" were played during Junior's testimony July 11.
Frank Jr. definitely has a few issues to work out with Dad. On July 3 he testified that his father sometimes held a gun to his face. Frank Sr. has been in court during his son's entire testimony, but the two men have not spoken directly. "It's very difficult for any parent to see his child testify against him," Frank Sr.'s attorney told reporters. Imagine, then, how much harder it is when a sibling gets into the act. Frank Sr.'s hit-man brother, Nick Calabrese, pled guilty on the same indictment and is scheduled to testify for the prosecution. Is Dr. Jennifer Melfi available for family therapy?
The "headphones" appear to be a way Frank Jr. was proposing that he disguise the wire. He was known to wear headphones constantly to listen to music.
The "jacket" appears to indicate an alternative to the headphones for wiring Frank Jr.