The Murder of Howard Appledorf
Kennedy was sentenced to four years in prison. At the time of the sentencing, he had been in jail for about a year and a month. He received credit for the jail time when transferred into the state prison system. After serving just over a year in prison, he was paroled on December 31, 1984. No disciplinary reports were made on Kennedy while he was in prison. DeCarlis recalled of Kennedy's incarceration, "His conduct was perfect. He got out and went to New York and I haven't heard from him since."
However, that was not the end of Kennedy's brushes with the law. According to an article by David Greenberg published in the Gainesville Sun, Kennedy was "sentenced to 90 days in jail in New York for some minor crimes" he committed in 1994. Greenberg wrote that New York attorney Steven Hoffner was Kennedy lawyer for those crimes and quoted Hoffner stating, "[Kennedy] seemed to me to be a troubled individual with mental problems. He was definitely paranoid. He was not an easy client. He did not have a real firm grasp on reality."
Those mental problems probably contributed to Kennedy's later obsession with fashion designer Todd Oldham. Kennedy's amorous fixation on the handsome, openly gay Oldham led Kennedy to yet another courtroom date and to a stay in a mental hospital.
According to that same Gainesville Sun piece, Kennedy, then 28, "reportedly sent Oldham bizarre love notes, erotic art and condoms, and loitered near the designer's SoHo offices." Greenberg reported that Kennedy included "locks of hair" in these missives.
A New York Beacon article by Samuel Maull reported that Todd Oldham sought an order of protection against Kennedy and that the fashion designer testified in court, "I truly believe that defendant will injure me and that my life is in imminent danger." The Gainesville Sun reported that Oldham received the restraining order that he requested.
Kennedy was arrested for stalking Oldham two days after being released from jail on the crimes committed in 1994. According to the Gainesville Sun, Kennedy pled guilty on May 11, 1995, to one count of harassment in exchange for the court's agreement to a "conditional discharge" of six other charges. Those other charges were for disorderly conduct and trespassing. Two of them involved Oldham and four were unrelated.
Kennedy was already in the Bellevue Hospital mental ward when he entered his plea and the condition imposed by Judge Judith Anne Levitt in the agreement was that he "remain in custody until two psychiatrists approve his release." The order of protection barring Kennedy from going near Oldham was extended for three years. Wayne Brison of the Manhattan district attorney's office said that Oldham approved the deal..