It was “Ditch Day” at Niles West High School, and a group of seniors played hooky in classic Chicago style — skipping classes to catch a Cubs game at Wrigley Field.

You might have expected the school’s dean, Gary R. Solomon, to be angry. But Solomon, then 29, wasn’t at all upset, according to school officials and students who remember that day in May 1997. That’s because he was in the Wrigley stands with the teenagers, according to court records.

Later, in 2001, Solomon was forced out of Niles Township School District 219 under a cloud after he was accused by his bosses of “immoral and unprofessional” conduct, including allegations he kissed a female student, covered up students’ drug and alcohol use and sent “sexually suggestive, predatory” emails to students, court records show.

For many teachers, it would have been a career-ending scandal. But Solomon, who has denied any wrongdoing, rebounded to build a highly profitable career in education. He went into business with a former Niles West student and started a trio of education firms that have gotten government contracts worth tens of millions of dollars.

Now, Solomon, who wasn’t charged with any crime, again finds himself under a harsh spotlight, his business empire at the center of a federal probe that prompted one of his former employees — Chicago Public Schools CEO Barbara Byrd-Bennett — to take a paid leave of absence on Friday.

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Subpoenas show federal authorities are seeking records from CPS pertaining to three north suburban companies owned by Solomon and Niles West graduate Thomas Vranas. They also seized records from them, according to a spokesman for their companies, who wouldn’t comment on the investigation.

Thomas Vranas

Thomas Vranas

One of the companies — a principal-training firm called SUPES Academy — was given a $20.5 million, no-bid contract from CPS in 2013.

Byrd-Bennett once worked for SUPES. She also has been called a “senior associate” of PROACT Search, another Solomon-Vranas venture.

The Chicago school system has paid a total of more than $15.2 million to the two men’s three companies.

In addition to their visit to the Chicago Board of Education, federal investigators took records from SUPES’ offices and Byrd-Bennett’s homes in Chicago and in Ohio, putting Mayor Rahm Emanuel’s administration into crisis mode just days after his re-election.

It’s an unwelcome return to the public eye for Solomon, who attended the University of Illinois at Chicago, was certified as a teacher in 1990 and taught social studies at Niles West and later was also made a dean.

In 1999, the Niles Township school board moved to dismiss Solomon. Beside improperly attending the Cubs game with students, the board said in court documents, Solomon had exchanged suggestive emails with current and former students on “numerous occasions.”

Records confiscated from Solomon’s computer indicated that, “on at least one occasion, you kissed a female student and/or had unprofessional relationships with students,” the board told him.

And photos seized from Solomon showed students drinking alcohol and using illegal drugs, the board said. It said Solomon knew a parent had supplied the booze and drugs but that he failed to alert the state Department of Children and Family Services, despite being a so-called mandated reporter.

Solomon also was accused of putting “obscene, profane, sexually oriented and/or racially offensive” material on district computers and allowing students to use his email account. He refused to answer questions or undergo a psychiatric evaluation, his employers said.

He fought the allegations aggressively. A two-year court battle ended with his resignation, but only after the district agreed not to seek to strip him of his teaching license and paid him $50,000 to settle the case.

For his next act, Solomon joined Princeton Review, the test-prep and college-admissions giant. One of his colleagues at Princeton Review was Vranas. Now 34, Vranas graduated from Niles West the same year the Niles Township board moved to force out Solomon.

Former classmates and teachers at Niles West don’t remember Thomas Vranas and Solomon being close there. Vranas was known as an outgoing and gifted student, headed for Northwestern University, where he majored in economics.

Niles West yearbooks show he was active in school activities — the Symphonic Orchestra, the Tutors club, the “West Helps Others” charity group and the Model UN club, as well as being a member of the National Honor Society.

Today, according to his online LinkedIn profile, he volunteers with Open Heart Magic as a bedside magician for children at Advocate Lutheran General Hospital in Park Ridge.

In 2008, Vranas and Solomon left Princeton Review within a month of each other, according to their LinkedIn profiles, and they went into business together. Their PROACT firm, which conducts executive searches for school districts, had clients in 45 cities in 24 states, according to a proposal it filed in August 2012 with officials in Norwalk, Conn.

In that application, the company listed Byrd-Bennett — who became Chicago schools chief three months later — as a “senior associate” with a PROACT e-mail address.

Listed as a reference in the proposal was Sherry Ulery, who worked under Byrd-Bennett at school districts in Detroit and Cleveland.

Ulery later reunited with Byrd-Bennett at CPS as her $175,000-a-year chief of staff. She was one of three of the CEO’s underlings whose employment records federal authorities demanded. She also is due to testify Tuesday before a federal grand jury in the case, according to the subpoenas delivered to CPS.

Another Solomon-Vranas venture, Synesi Associates, worked for the Detroit schools when Byrd-Bennett was a top official there, records show.

Synesi got a contract from CPS in 2013 to perform professional development services in a part of the district overseen by Byrd-Bennett aide Tracy Martin. Like Ulery, Martin had worked for Byrd-Bennett in Cleveland and Detroit. The subpoenas asked for records pertaining to both of them.

CPS records show the district has paid Synesi and PROACT a total of about $300,000.

By far the most lucrative Chicago schools deal for Solomon and Vranas, though, was the SUPES contract. CPS has paid the company nearly $15 million.

Vranas signed the no-bid contract with CPS as president of SUPES in June 2013.

Some former classmates from Niles West who remember Vranas and Solomon were surprised to hear they are business partners.

“We still talk about what happened with Mr. Solomon when we get together,” said a 1999 graduate of the Skokie school who asked not to be named. “I just can’t believe that he’s still in education.”