A day after Chicago Public Schools filed a $1.6 million lawsuit against him for allegedly embezzling funds, Roberto Tirado’s mysterious case continues to offer more questions than answers, including: could he really have acted alone?

Two years ago this week Tirado was found dead in a hotel room in Tijuana, Mexico, according to the U.S. State Department.

Back in Chicago, the Lake View High School graduate had been a well-respected wrestling and swim coach at his alma mater where he also served as the school’s technology coordinator.

It was in that role that Tirado allegedly misappropriated nearly half a million dollars from school funds, over 10 years, through nine fake vendors, according to a CPS Inspector General’s report released this month.

“The vendors were actually individuals [he] knew when he went to high school or they went to high school when he worked there,” Inspector General Jim Sullivan told WBEZ. “So he created those vendors for CPS. And, over the course of a number years, he issued purchase orders and caused them to be paid in excess of $400,000.”

The report recommended that CPS try to recover some of the lost funds, and yesterday, CPS filed its lawsuit against Tirado’s estate to do just that.

Still many, like former Lake View special education teacher M.L. Rembert, wonder how a single employee could divert so much money through bogus vendors without setting off alarms. 

“I’m still in a state of shock,” Rembert said. “I can’t believe that administrators that worked with this individual could, without checks and balances, not be aware of this. I find it so appalling. This was not the individual that I knew.”

Tirado’s alleged misappropriations were discovered during a routine audit of the school triggered by the arrival of a new principal Lilith Werner in the summer of 2011.

When the auditor discovered unusual reimbursements to Tirado, she brought in the CPS Inspector General’s office, which Sullivan, says, found “more serious issues.”

These included funneling the money through bogus purchase orders to vendor P.O. boxes that Tirado had established in Evanston, according to the IG’s report. In addition, more than $114 thousand of reimbursements from the school went to Tirado’s personal American Express card.

The report said that Tirado did not cooperate with the Inspector General’s investigation on the advice of legal counsel. But Tirado’s lawyer, Kevin O Rourke, did tell the IG’s office that: “Mr. Tirado stated that everything he’d done was at the behest of his school principal.”

Sullivan confirms that O’Rourke shared this information, and that IG representatives interviewed former Principal Scott Feaman.

Feaman isn’t named in the report, but he oversaw the school for all 10 years in question, including when Tirado allegedly reaped more than $114 thousand in credit card reimbursements. District rules prohibit most personal reimbursements of more than $500 a month. And in a statement CPS says principals are “required to monitor school spending.”

So how did Tirado get away with so much money?

According to the report, Tirado may have received help from two Lake View high school clerks who who did not observe the proper checks and balances to prevent fraud. The two were recommended for disciplinary action, and no longer work at Lake View. But the IG said reimbursing monthly amounts over $500 should have required additional scrutiny from a higher authority.

“You can exceed that $500 limit with a little more oversight,” Sullivan said. “So to explain how that happened and this fell through the cracks, I really can’t explain that at this point.”

However, Sullivan says by the end of the investigation, “we didn’t think there was enough evidence to make any [disciplinary] recommendation for Principal Feaman who had already left CPS employment by that time.” 

When Feaman retired from Lake View in 2011 he was honored by Chicago’s city council for 36 years of service to CPS. WBEZ made multiple attempts to reach Feaman for comment through phone, email and even a visit to his home. In one call to his household someone picked up the phone and responded, “we have nothing to say” before hanging up.

Lake View’s current principal Lilith Werner also did not respond to requests for comment on the matter. Nor did the two clerks who were implicated in the IG’s report.

While the IG’s part of the investigation is closed, Tirado’s friends and associates say they’re still left with many questions.

They ask why someone with access to so much money would have continued to work multiple jobs. Others question how he died in Tijuana (his lawyer O’Rourke says he still doesn’t know). Some ask why, after dying in January of 2012, Tirado’s body was not transferred to Chicago until March.

Sullivan’s office confirms that it never identified the body when it returned.

Tirado’s family did not respond to interview requests but, after the report came out, one aunt sent WBEZ a note saying:

“As you can imagine, the family was taken aback by the report and had a number of questions regarding the content. We feel that it is unfortunate that Robert is the one being targeted as he is no longer with us. On a personal note, I can share that this caused the family a great deal of pain. It was the reopening of the wound of having lost Robert.”

O’Rourke says that the family was further shocked by the Monday lawsuit that designates a CPS employee, rather than a family member, as the personal representative of Tirado’s estate.

Josh Conlan was a student at Lake View from 2001 to 2003. He says that Tirado, was a challenging wrestling coach who inspired him to pursue a degree in physical education. Conlan feels the charges don’t fit the man he knew.

“Im picturing Robert Tirado in my head right now and I can’t see anything you are saying,” Conlan said. “Half a million dollars at that time? There’s gotta be other names attached to it. Knowing what I know about him, I can’t specifically say that he is a mastermind of that sort. And it just seems to me like they are trying to find a fall guy. And that’s just wrong.”

Several others echoed Conlan’s comments. But the IG says that $330 thousand dollars did end up in Tirado’s account. What happened to all the money after that is still unclear, but documents that emerge from the CPS lawsuit may shed light on that.

No criminal charges have been filed in the matter and Sullivan said that the FBI lost interest in the case after Tirado was declared dead.

It’s difficult to know what Tirado was thinking in the months between the audit and his disappearance, and he left few clues. But one friend, who asked to remain anonymous, shared a letter in which Tirado said he felt like a failure who “let down so many people.” He closed the letter with a warning: ‘Be careful to whom you talk.”

O’Rourke confirmed that his client was depressed. 

“Mr Tirado’s life was [Lake View high school] which is why when asked him to leave and said get off the school grounds now, it was devastating to him.”

The lawyer also contends that, until the end, Tirado maintained he was simply following orders. 

“They were using the funds basically off-budget as a way of circumventing the CPS budgeting rules,” O’Rourke said. “And Mr. Tirado told me that this was a common practice at many schools.”

Inspector General Sullivan responds that, although he has seen cases involving suspicious reimbursements to personal credit cards before, fake vendor schemes are “certainly not commonplace at CPS.”  

And while the IG acknowledges that he’s investigated bigger cases of misappropriation in CPS, “it’s still a large amount of money that could have been used otherwise for appropriate purchases at the school.”

While the IG’s report offers information about dates and dollar amounts, other details are frustratingly out of reach for friends like Rembert. 

“I look at this and say ‘this can’t have happened,’” she said. “There’s more to it than meets the eye. I just wish the investigation had been more thorough. Roberto’s dead now. So, of course, this is the end of it. The man is dead. So I guess because he’s dead we won’t really ever get to the truth.”

Monica Eng is a WBEZ producer. Follow her at @monicaeng