Before his principal-training company came under federal criminal scrutiny for its lucrative deal with Chicago Public Schools, Gary Solomon previously faced allegations he used racial slurs in emails sent as a north suburban high school dean, according to documents released Thursday by his former employers.

Solomon is one of the owners of SUPES Academy, which received a $20.5 million no-bid contract from CPS in 2013. The FBI is investigating the awarding of the contract, and CPS CEO Barbara Byrd-Bennett — who once worked for SUPES — has taken a paid leave of absence after the existence of the federal corruption probe became public recently.

In 2001, Solomon was forced out of Niles West High School after his bosses accused him of “immoral and unprofessional” conduct, including allegations he kissed a female student, covered up students’ drug and alcohol use and sent “sexually suggestive” emails to students, the Chicago Sun-Times has reported.

Now, newly obtained records from the Niles Township High School District 219 shed additional light on the allegations against Solomon while he was an administrator and social studies teacher there.

FROM THE ARCHIVES
The 2001 settlement between Niles and Solomon

In an email to a former female student who had recently graduated, Solomon allegedly referred to African-American people as “mooks, shines, burrheads, yard apes, porch monkeys,” and several other racially offensive terms.

He also wrote that black people “will never set foot in his house,” according to a transcript of a state hearing held because Solomon initially fought efforts to remove him from the school.

And, in a personal journal he kept on a school computer, Solomon described another school administrator as an “uppity n—–,” a lawyer for District 219 alleged, according to the transcript.

On Thursday, Byrd-Bennett — who is African-American — said she was unaware of the allegations against Solomon. She referred all other questions to her lawyer, who did not return calls.

A spokesman for Solomon declined to comment.

The documents from the case, which were released in response to a Freedom of Information Act request by the Sun-Times, also detail what Solomon’s former employers called his “predatory complex.”

“Mr. Solomon would pick on unsuspecting victims, minor female students, most of whom suffered from an eating disorder, anorexia, bulimia, psychological self-doubts about themselves, alcohol and substance abuse, and prey on them,” said Anthony Scarino, the lawyer who represented District 219 in its push to remove Solomon from his job there, according to a transcript of the state administrative hearing in 1999.

In an email to a female student, Solomon allegedly asked, “Do you think you are a good flirt?” according to the transcript.

A day later, he wrote to the same student again, allegedly asking her several questions: “What position do you sleep in? What clothes do you sleep in? When are you most vulnerable? Completely describe your bedroom. What are you favorite turn-ons?”

The student hand-wrote responses to those questions, according to the school district, and that document was allegedly found in Solomon’s school office along with photographs of the female student.

In his journal, Scarino said, Solomon wrote of one student: “She is there for the taking.”

A district official who searched Solomon’s office testified that she found an email he sent a student that said, “We stepped way across the line countless times and violated all the bull—- ethical lines that people say students and teachers should not cross. I invited you to know me as a person, not as a teacher.”

In another document, labeled “fantasy,” that Solomon allegedly kept at the school, a sexual encounter was graphically described between a dean and a student on Solomon’s office floor.

A school administrator had warned Solomon he had “boundary problems with female students,” the records show. Still, Solomon allegedly engaged in “several unprofessional relationships with female students . . . including, on at least one occasion, kissing a female student,” and tried to cover it up, Scarino said.

Solomon’s lawyer shot back at the hearing that the Illinois Department of Children and Family Services and Skokie police were informed of the allegations against him and nothing came of that.

The lawyer, George Grumley, said DCFS determined the allegations were unfounded. As for the Skokie police, Grumley said they too looked into the charges but “didn’t do anything. They couldn’t find any crime.”

Grumley said Solomon had acted in a “tremendously imprudent” fashion by putting his journal on a hard drive at work but did not deserve to be fired.

“It was a dumb thing to do but he didn’t pass it around amongst the student body,” Grumley said.

The lawyer also rebutted the district’s charge that Solomon led students on a “ditch day” trip to Wrigley Field, saying he had proof that ”school wasn’t in in session during the game.”

District 219 trustees approved paying $50,000 to Solomon and the law firm that represented him to settle the dispute in February 2000. Under the terms of the deal, Solomon resigned.

At the time, District 219’s board president said the settlement was positive for the schools because “it makes sure that this individual will never work in the district again” and would save on legal fees.

Solomon went on to form three companies with Thomas Vranas, who was a Niles West student while Solomon worked there. The two business partners and all three of their companies are mentioned in federal grand jury subpoenas recently served at CPS.