Jonathan is a trial attorney who also represents school districts and private schools in various matters. He has represented districts in dozens of impartial hearings for students with disabilities, and in appeals of such cases to the Office of State Review. Jonathan has defended school districts in IDEA and Section 504 in cases in federal district court and on appeal to the United States Court of Appeals.

He has represented districts in numerous investigations by the Office of Civil Rights of the United States Department of Education and by the New York State Department of Education.

Jonathan has also handled numerous cases regarding student discipline, including appeals to the New York Commissioner of Education and challenges of discipline in the courts. He represented the district in Wisniewski v. Weedsport Central School District, 494 F.3d 34 (2d Cir. 2007), in which the court upheld a suspension of a student for posting online threats against a teacher. Jonathan represented the district in Kearney v. Ithaca City School District, 19 N.Y.3d 481 (2012), in which the Court of Appeals held that the Division of Human Rights lacked jurisdiction over claims by students against public school districts.