Things are looking grim for county schools chief Jon Gundry. Last week, a judge ruled that a lawsuit could continue to trial against the superintendent and the Santa Clara County Office of Education (SCCOE), which oversees 31 school districts in the South Bay. Micaela Ochoa, the former chief business officer for the SCCOE, accuses Gundry of wrongful termination and retaliation against her and others after they refused to help him break the law. In one instance, Ochoa says, Gundry tried to get staff to misreport his moving expenses to the IRS so he could avoid paying taxes. On another occasion, Ochoa informed the superintendent that he and his communications director, Ken Blackstone, were not complying with the Public Records Act by hiding consulting contracts requested by San Jose Inside. In that instance, Gundry was found to be signing secret deals just a dollar under the $100,000 threshold that requires him to inform the elected board of trustees. It gets worse. Ted O, the SCCOE’s former director of internal business services, gave a deposition in which he said that Gundry was often paranoid and berated staff. O said that he was so concerned Gundry might attack him that he bought pepper spray. Maribel Medina, formerly the SCCOE’s top attorney, also filed a lawsuit against the SCCOE and the superintendent after being fired by Gundry in 2015—together, Medina and Ochoa’s departures cost taxpayers more than half a million dollars in payouts. In her deposition, Medina said that the superintendent told her to answer him by saying, “Si, señor.” In response, Medina reportedly accused of him of treating her like a Mexican day laborer instead of an attorney. The SCCOE board will have to decide if it wants to settle the lawsuits or go to trial, but trustees could be closing in on another big decision. The board has been evaluating Gundry’s job performance in closed session since mid-January. Blackstone, who told Fly the SCCOE would not comment on pending litigation, has seen his position eliminated through layoffs. His last day is June 30.