By late summer, the prosecution brought forth three more women who claimed that William assaulted them. One woman claimed that in 1983 while at a New York City party she met William, a cousin of her boyfriend. Nancy Gibbs stated in her August 1991 Time article that the woman accepted William's offer to sleep at his guesthouse after she had drunk too much at the party and while there, he assaulted her. According to the article, the woman claimed that, "one moment he was standing in front of me, talking with me, saying good night to me...and the next minute he had tackled me onto the bed and was trying to kiss me and had his body completely over mine...and he wouldn't stop." However, she never filed a report with the police after the incident because there were no witnesses and she thought she wouldn't be believed.

A 26-year-old New Jersey medical student also came forward claiming that in May 1988, William raped her at his home after a party in Washington, D.C. The woman didn't tell the authorities what happened because she was afraid of the unwanted publicity since William was a Kennedy. Moreover, she worried that no one would believe her story.

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A third woman, a doctor, also came forth and agreed to testify at the upcoming trial, claiming that William attempted to rape her at his Palm Beach, Florida apartment in 1988. Yet, he allegedly let her go after she repeatedly protested. She too failed to alert the authorities as to what happened that night, fearing that she would not be believed. The Kennedy family was just too intimidating to confront.

The prosecution team led by attorneys Moira Lasch and David Bludworth wanted to introduce the three women's testimonies at trial, hoping to prove that William had a history of sexual assault. There was no doubt that their testimony would significantly damage his credibility. Realizing the potential harm to their case, the defense team led by attorneys Roy Black and Mark Schnapp filed a motion to prevent the women's testimonies from being heard in court.

Florida law prohibited a defendant's sexual history from being introduced during a trial if two requirements weren't met by the state. According to the defense motion, case no. 91-5482-CF-A-02, the State of Florida v. William Kennedy Smith, the prosecution had to demonstrate that the evidence they were offering was "relevant to prove a material fact in issue" and that the cases were "strikingly similar to the charged offense." Immediately prior to the trial, the defense team, "argued that the three cases did not represent a 'signature style' and that the only real question in the Palm Beach case was whether the women consented or not," Booth reported. If this could be proved, the prosecution wouldn't stand a chance.