Wisconsin Principal 'Had Sex Just About Every Day At School'

KENOSHA, WI — The former principal of a Wisconsin high school has been charged in court after authorities say he sexually assaulted a former student multiple times.

Authorities say Curtiss Tolefree was the Dean of Students at Bradford High School in 2008 when he reportedly had a sexual relationship with a 17-year-old junior. The relationship started in 2008 and continued into the following school year, the report stated.

In the fall of 2008, at age 17, the woman and Tolefree had sex for the first time, according to the complaint. The woman told authorities they "had sex just about every day at school" for the rest of the 2008-09 academic year, according to the probable cause affidavit in support of the charges.
Tolefree has not responded to a request for comment about the charges.

The woman described staying at school with Tolefree until 7 to 8 p.m., sometimes working out together before or after having sex, the complaint alleged. The incidents also took place at Tolefree's Kenosha home or in Tolefree's SUV in the alley behind her mother's house or on a nearby side street, according to the complaint.

"She viewed him as her best friend," the complaint said.

Tolefree would call the student out of class to have her come to his office where they would have sex during the school day, prosecutors said.

The two spent an entire weekend together at a La Quinta Inn in Kenosha during the girl's junior year before visiting another hotel near the Cheesecake Factory at Westfield Old Orchard shopping center in Skokie, having sex at both locations, according to the charges. That incident has not yet led to any criminal charges since it took place in Illinois.

According to the charges, the relationship continued over the summer and the next year, even though Tolefree had changed offices. The student told investigators she began a relationship with someone else in 2010. At that point, Tolefree changed his tune, prosecutors said.

"[She] reports that [Tolefree] told her that she should be focusing on school, and she should not be getting into a relationship with someone. [She] states that she could tell that [Tolefree] was jealous. [She] reminded [Tolefree] that he was the one that was married so," according to prosecutors, "he had no room to talk."

Tolefree left Bradford in 2009 to become assistant principal at Washington Middle School in the Kenosha Unified School District. He returned to the high school as assistant principal from 2012 to 2014, when he was hired as principal of Washington.

In July 2018, Kenosha Unified School District Superintendent Sue Savaglio-Jarvis called for a termination hearing to remove Tolefree from his $110,000-a-year job as principal, filing a 10-page list of charges.

According to the "findings of fact" accompanying the statement of charges, school district staff received a complaint in May 2018 involving an inappropriate relationship between Tolefree and a subordinate at Washington Middle School that created an "intimidating and hostile environment." Tolefree later resigned during the course of that investigation, according to district documents.

The Zion Elementary School District later hired Tolefree to become the principal at Beulah Park Elementary School. District 6 Superintendent Keely Roberts told parents that Tolefree was placed on administrative leave as soon as district officials learned of the charges. She said the district conducts criminal background checks and cross-references state and national sexual and violent offender registries before hiring people.

Tolefree is due in court in Kenosha County for his initial appearance on Jan. 2 at 1 p.m.

Additional reporting by Jonah Meadows, Patch Staff