“They’re planning a . . . tax increase announcement and no one told me!!!!!! I think I need to get out of here,” Byrd-Bennett wrote to Gary Solomon, her former employer whose SUPES Academy principal-training firm had been given a $20.5 million, no-bid contract with CPS soon after Mayor Rahm Emanuel put her in charge of the city’s schools. “Anyway really pissed.”

“Sorry you are frustrated,” Solomon replied. “Screw them for taking things for granted.”
It was one of a series of email exchanges during Byrd-Bennett’s 2 1/2-year tenure as Mayor Rahm Emanuel’s handpicked schools chief in which she confided in Solomon, who’s now at the center of a federal investigation, newly obtained CPS emails show.
Solomon’s SUPES Academy also offered Byrd-Bennett speaking engagements three times — and an “honorarium” for one appearance — after the Chicago Board of Education gave his company the no-bid deal in 2013, the records show.
Byrd-Bennett replied to the offer by saying she would check with lawyers at CPS to see whether that would be allowed.

A CPS spokesman wouldn’t say whether Byrd-Bennett had sought that legal opinion or whether Solomon’s company paid to have her speak.
“I cannot comment due to the ongoing investigation,” CPS spokesman Bill McCaffrey said.
Byrd-Bennett took a paid leave of absence in mid-April after CPS revealed federal investigators had subpoenaed them for records regarding her, some of her top aides and three companies owned by Solomon and his business partner Thomas Vranas. She resigned her $250,000-a-year post as chief executive officer about six weeks later, effective June 1.
Before coming to work for CPS in 2012, initially in the district’s No. 2 post, Byrd-Bennett had worked for two companies owned by Solomon and Vranas, including Wilmette-based SUPES Academy — the company that was given the $20.5 million deal to train school principals.
After Byrd-Bennett stepped aside, interim CPS CEO Jesse Ruiz dumped SUPES, costing the firm more than $7 million of the $20.5 million.
No charges have been filed in the case.
Byrd-Bennett didn’t respond to messages seeking comment.
Dennis Culloton, a spokesman for Solomon and Vranas, said: “It is well known Barbara Byrd-Bennett was a colleague and former consultant for Mr. Solomon’s companies prior to her service to Chicago schools, so the email exchanges are nothing new. None of Mr. Solomon’s companies ever paid Ms. Byrd-Bennett an honorarium for any speaking engagement.”
The emails, which CPS released in response to a request made under the Illinois Freedom of Information Act, show Byrd-Bennett frequently turned to Solomon to complain about her problems running the nation’s third-biggest school system and also about perceived slights from City Hall.
In June 2013 — the month the SUPES contract was approved — she forwarded Solomon an email from an aide who’d informed her about the “property tax announcement” coming a few days later.
In that email exchange, she also threatened to complain about City Hall to reporters, as her predecessor in the top schools job, Jean-Claude Brizard, had done after he was forced out.
“I am simply a convenience and when I announce I will leave … ” Byrd-Bennett wrote.
Beside offering her sympathy, Solomon, apparently referring to Emanuel, added, “Really, I hope he is enjoying Israel.”
At the time, the mayor was in Israel, where he’d traveled with his family to celebrate his daughter’s bat mitzvah.
Byrd-Bennett replied by thanking Solomon for “allowing me to vent.”
“I am not sure they get what they are doing,” she wrote. “I just cannot be lead [sic] around by the nose like this … just not who I am.”
Solomon offered to meet at Byrd-Bennett’s office “if you can sneak me in.” The next morning, she wrote to her assistant, “If Gary stops by I need to see him.”
In an email exchange a few weeks later, in July 2013, Byrd-Bennett wrote to Solomon: “Thank you for the time yesterday to allow me to catch my breath, catch up and just be in a safe space.”
She wrote that the administrator-training program that Solomon was overseeing for CPS was a high priority “both to the mayor and I.”
“I am betting the farm on this,” Byrd-Bennett told Solomon. “And finally, I really need time for a ‘cup of tea’ with your parents.”
Four minutes later, Solomon replied, “Thank you thank you thank you for everything. Really. And we need to make time for one another to just get together and laugh. As tired as we are, as hard as we work, I think it’s important we get together and just laugh a lot.
“My parents scare me, by the way,” he wrote. “I would prefer we share our drinking with just one another.”
Byrd-Bennett wrote back, “Yes, and yes and ah ha … I love them.”
When Beth Swanson, Emanuel’s longtime top aide at City Hall on education issues, stepped down from that post, Byrd-Bennett forwarded Swanson’s resignation announcement to Solomon.
In that email, sent at 3:58 a.m. on July 31, 2014, Byrd-Bennett told Solomon, “I was in the car with others when we talked and could not share the full details with you!”
“Wait!!! Go back to bed, young lady!!! It is not yet 4 a.m.!!!!!!! I am the only idiot that is up at this hour,” Solomon replied.
Solomon’s business partner, Vranas, made the first of three emailed offers of speaking engagements at SUPES events to Byrd-Bennett in September 2013.
“I know it would mean the world to our cohort to hear from you,” Vranas told Byrd-Bennett of a SUPES conference for “60 senior administrators” from around the country. “Of course we would pay any travel and lodging costs and we could have an honorarium to you or a non-profit of Ex-CPS CEO confided in figure in fed probe, emails show | Chicago Sun-Times: