Jonathan Fey #

Introduction #

Jonathan M. Fey is a former high school principal whose decade-spanning career in Bay Area education ended in scandal. Fey, 54, served as principal of Amador Valley High School in Pleasanton, California, from 2022 until October 2025, when he resigned as part of a settlement with the Pleasanton Unified School District after a third-party investigation substantiated allegations that he had used the dating and hookup app Grindr to pursue sexual relationships with a current and a former student. The case drew regional attention not only for its substance but for its unusual procedural shape: Fey received a $254,000 settlement, exited without any admission of wrongdoing, and maintains that the allegations are false.

Background Information #

Fey built a long career in California public education, spanning more than 30 years. Before joining Pleasanton, he worked in the Fremont Union High School District and spent eight years with the Mt. Diablo Unified School District, where he served in school administration; he has described his reputation there as “built on integrity and commitment.” He was hired as principal of Amador Valley High School, one of the East Bay’s most prominent comprehensive high schools, in 2022. A married father, he lived in Pleasanton at the time of the allegations.

The Controversy or Incident That Led to Their Cancellation #

Allegations. The claims in this section are allegations from a Pleasanton Unified School District administrative investigation, which reported substantiating them. They were never admitted by Fey, never criminally charged, and never adjudicated in court. Fey denies all of them and claims impersonation.

The controversy began in August 2024, when a 2023 Amador Valley graduate told the district he had been contacted on Grindr by an account using only an “eyes emoji” as its username, which he believed belonged to Fey. The student reported that the day after the first Grindr exchange, Fey followed him on Instagram — a timing he found impossible to believe was coincidental. He later provided the district with screenshots of the conversations. A second recipient of “eyes emoji” messages — then an 18-year-old senior at Amador Valley and one of Fey’s own students — came forward during the investigation. Screenshots published in the investigative record show the account complimented the students’ physical appearance (telling one he was “hella hot”), pressed for secrecy (“For sure I need this to stay a secret”), floated meeting up “before you go back to (college),” and proposed what it called a “secret school tryst.”

The district placed Fey on indefinite administrative leave on August 12, 2024, and contracted an outside investigator, whose February 2025 report sustained the key allegations — including a conclusion of probable cause to believe Fey engaged in sexual solicitation. The investigator noted the account holder had “intimate knowledge” of one student’s personal life, with specific references to on-campus interactions and school trips. A separate witness told the investigator she had once seen Fey’s phone open to the Grindr app while he chaperoned a school event. On February 28, 2025, the district notified Fey that it intended to fire him.

Fey has consistently and categorically denied the allegations. He claimed the “eyes emoji” account was not his and that he had instead been impersonated, pointing to past instances of Amador Valley students posing as others online; he reported the alleged identity theft to Pleasanton police, though the department confirmed that no criminal report was filed and no arrests were made. “The allegations made against me are false,” Fey said in a written statement issued through a San Jose public relations firm.

Public Reaction and Consequences #

Allegations. The findings described below come from the district’s administrative investigation, not a court. Fey disputed them throughout and settled without any admission of wrongdoing.

Rather than proceed to a contested administrative hearing, Fey and the district reached a settlement: signed October 18, 2025, and unanimously approved by the Board of Trustees in closed session on October 23, it allowed Fey to permanently resign effective October 17 in exchange for a $254,000 payment — roughly half earmarked for attorney’s fees, with about $142,000 described as back or front pay — and no admission of wrongdoing. Fey dropped his administrative appeal and agreed not to sue the district. The district said it settled to spare students and staff from testifying at an adversarial hearing and to preserve litigation resources.

The underlying records became public only after a yearlong fight. The Pleasanton Weekly and EdSource had pursued the documents under the California Public Records Act since September 2024; Fey filed a “reverse-PRA” lawsuit under the name John Doe to block their release, winning a temporary restraining order, before that suit settled and roughly 350 pages of investigative records were released in late October 2025. Under state law, the district must also report the matter — including the investigator’s probable-cause finding of sexual solicitation — to the California Commission on Teacher Credentialing, which could move to rescind Fey’s teaching credential; the confidential findings remain visible to potential school-district employers for five years. No civil lawsuits against Fey had been reported as of the initial coverage.

Current Status #

Fey is permanently separated from the Pleasanton Unified School District and, as of the latest reporting, has not taken another public education role. His administrative proceedings were dismissed as part of the settlement, and his credential now sits before the state credentialing commission, which conducts its own investigation and could revoke the license he would need to lead or teach in another California district. He continues to deny any misconduct, asserting that the Grindr account was an impersonation and that no direct evidence ties him to the messages.

Impact on Their Career/Life #

The scandal ended Fey’s three-decade career in public education and his tenure at one of Pleasanton’s flagship high schools, which cycled through temporary administrators before appointing an acting principal for the remainder of the 2024–25 year. The substantiated findings and the mandatory credentialing report create a durable obstacle to any future school-administration work in California, regardless of the settlement’s no-admission terms. The case also became a touchstone locally on two broader issues: the multi-billion-dollar wave of California litigation over historical school sexual-abuse allegations, and the public’s right to see investigation records when districts settle with accused administrators — a fight the Pleasanton Weekly editorial board framed as the heart of the story.