Despite his insistence that his professional code means that he is not responsible for worrying about the actual content of the conversations he records or the uses to which his clients put his surveillance activities, he is, in fact, wracked by guilt over a past wiretap job that left three people dead. His sense of guilt is sharpened by his devout Catholicism. His one hobby is playing along with his favorite jazz records on a tenor saxophone in the privacy of his apartment.
Caul and his colleague Stan (John Cazale) have taken on the task of monitoring the conversation of a couple (Cindy Williams and Frederic Forrest) as they walk through crowded Union Square in San Francisco. This challenging task is accomplished. After Caul has worked his magic on merging and filtering different tapes, the final result is a sound recording in which the words themselves become crystal clear, but their actual meaning remains ambiguous.
Although Caul cannot understand the true meaning of the conversation, he finds the cryptic nuances and emotional undercurrents contained within it deeply troubling. Sensing danger, Caul feels increasingly uneasy about what may happen to the couple once the client hears the tape. He plays the tape again and again throughout the movie, refining its accuracy (by catching one key, though ambiguous, phrase hidden under the sound of a street musician: "He'd kill us if he got the chance") and constantly reinterpreting its meaning in the light of what he knows and what he guesses.
Caul avoids handing in the tape to the aide (Harrison Ford) of the man who commissioned the surveillance (Robert Duvall). He then finds himself under increasing pressure from the aide and is himself followed, tricked, and listened in on. The tape is eventually stolen from him in a moment when his guard is down.
Caul's appalled efforts to forestall tragedy ultimately fail and it turns out the conversation might not mean what he thought it did - the tragedy he had anticipated is not the one which eventually occurs. In the final scene, he discovers that his own apartment has been bugged and goes on a frantic search for the listening device, tearing up walls and floorboards and ultimately destroying his apartment to no avail. At the film's end he is left sitting amidst the wreckage, playing the only thing in his apartment left intact: his saxophone.
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