The Office of Special Investigations of the New York City Department of Education launched an investigation of McCaskill on February 2, 2006, concerning unpaid enrollment of New Jersey resident McCaskill's daughter in a New York City public school, which is illegal for non-residents of the city. Dr. McCaskill produced a lease claiming that he rented an apartment in Brooklyn, but the copyright date on the lease was after the signatures were dated. On February 6, McCaskill announced his resignation from Brooklyn Tech and agreed to pay $19,441 in restitution.