Former dean of students accused of sexual assault makes initial appearance in court

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KENOSHA -- Curtiss Tolefree Jr. made his initial appearance in Kenosha County court on Thursday, Jan. 2 on sexual assault charges.

The alleged victim in the case didn't disclose what happened until a year ago, but the statute of limitations allows victims of these kinds of crimes until the age of 45 to report.

Curtiss Tolefree Jr.

Prosecutors say Tolefree had a sexual relationship with a 17-year-old student at Bradford High School from 2008 to 2009 -- when Tolefree was the dean of students.

According to a criminal complaint, the victim came forward to Kenosha police detectives about the alleged criminal activity in 2018. She told them she and Tolefree would have sex nearly every day of her junior year -- often in his school office.

While discussing Tolefree's bail, the prosecution requested Tolefree have no contact with the victim, as well as anyone under the age of 18. The state also asked that he not talk to any witnesses, but did not provide a list of names to the defense.

Curtiss Tolefree Jr.

According to the complaint, the woman told detectives that she got into trouble quite often as a student and would get sent to Tolefree's office. She told detectives she spent a lot of time in his office -- and eventually began eating lunch there every day. The woman also told officials that Tolefree had his office window "covered with construction paper." As a result, if Tolefree's office door was closed, no one could see inside.

The complaint also stated the woman -- referred to as Jane Doe -- told authorities that around October or November 2008, when she was 17, Tolefree had sex with her in his office for the first time. "Jane Doe states that after the first time the defendant had sex with her in his office, they had sex just about every day at school during her junior year," the complaint states.

Curtiss Tolefree Jr.

Jane Doe also reports that there were times during her junior year that Tolefree would call her out of class  -- and have her come to his office to have sex. The complaint indicates Tolefree also had sexual encounters with the student in his SUV, his home, and hotels.

Jane Doe told detectives that her mother was the only person to ever question her relationship with Tolefree. Jane Doe says she always denied that anything was going on.

According to the complaint, Jane Doe states that around Dec. 31, 2009, she told Tolefree that she met and developed a relationship with someone else. She claims he became upset and told her "she should be focusing on school and should not be getting into a relationship with someone." Jane Doe claims she then told Tolefree that what they had been doing was wrong.

The judge ruled Tolefree could continue going to work and church but cautioned him not to have any inappropriate contact with children -- releasing him on a $10,000 signature bond.

Tolefree is the principal at an elementary school in Zion, Illinois. He has since been placed on leave and is due back in court for a preliminary hearing on Jan. 17. He faces three counts of sexual assault of a student by school staff and two counts of exposing genitals to a child.

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