The New York City schools investigator says the assistant principal secretly read emails of several principals and a school superintendent using computer spyware.
He says it was all motivated by a love triangle.
This investigation which began at Randolph High School is laid out in a report.
It involves no less than three different high schools, three principals who are the alleged victims, and a high school superintendent, and one assistant principal who are now accused in a tangled web.
"It looks like it was a very chaotic situation," said Richard Condon, the Special Commissioner of Investigation for New York City Schools.
Condon described the disturbing allegations to Eyewitness News that were made against Milciades Pepin, an associate principal for technology at three high schools, Randolph, Manhattan Center for Science and Math, and the Unity Center for Urban Technologies.
The school's principals were his alleged targets.
"He was opening their emails. He was sending emails in their name that were fictitious. He was erasing emails that were meant to be sent to people. At one point he even sent an email to the chancellor," Condon said.
Investigators say they relied on Pepin, giving him their cell phones, and having him fix problems with their computers over the last two years.
He hacked into their email accounts both personal and private.
"Yes both their DOE and their private email accounts," Condon said.
Randolph's principal, Henry Rubio, first became suspicious after the investigation shows he received disturbing email messages beginning in 2008.
Manhattan Center's principal, David Jimenez, says he was told by Pepin as revealed in the investigation, "When people mess with technology people, those people will get what they deserve."
"He disliked Jimenez too because Jimenez confronted him about some of the things he was doing," Condon said.
Investigators say they discovered Pepin was using "FlexISpy" Software to access the accounts, which they claim he had gotten for then Manhattan High School Superintendent Francesca Pena.
During the course of the probe investigators say they learned Pepin and Pena were also involved personally.
"They started to have an affair, and of course she was supervising him, at least indirectly, so that is a problem," Condon said.
Reaction from the Department of Education reads in part, "Both Superintendent Francesca Pena and Assistant Principal Milciades Pepin engaged in serious wrongdoing and undermined their ability to continue as leaders in our school system. When confronted with the report, Ms. Pena resigned irrevocably. We are also taking steps to terminate Mr. Pepin."
"When you interfere with the communications going back and forth with the people in the Department of Education, you are actually disrupting the educational process," Condon said.