[1] Upon his election in 2010, the OCR within the Obama administration took the position that Title IX protects LGBT students from harassment on the basis of sex stereotypes.

[9][6] After the regulation was adopted, Grimm continued to face gender-based discrimination by the school board even after he began hormone therapy (which altered his physical form), underwent reconstructive chest surgery, and received an official Virginia state I.D.

[11][12] In legal court proceedings, Grimm asserted he had been allowed to use the boys' bathroom for seven weeks without incident and had faced gender-based discrimination after the regulation of the Gloucester County School Board was implemented.

Prior to the hearing, on December 18, 2014, the ACLU had already filed a complaint with the U.S. Department of Justice (DOJ), based on the nature of the school board's restroom policy.

In his ruling, Judge Doumar held that Title IX's operative provision should be read narrowly to cover discrimination on the basis of genetic "sex" only, and not gender identity or expression.

[6] During the proceedings in the District Court, Judge Doumar made a number of idiosyncratic statements from the bench, saying that being transgender is a "mental disorder",[14] delivering off-topic criticism of the federal government on the issues of marijuana enforcement[7] and sanctuary cities,[14] and explaining that Grimm is a female who "wants to be male".

[7] In reviewing the case, the Court of Appeals criticized Judge Doumar's conduct in the courtroom, writing that his "extraneous remarks [and] suppositions ... marred the hearing".

The majority held that the District Court had ignored the guidance in the Ferg-Cadima letter from the Department of Education, the controlling agency in Title IX protections in the context of the Chevron and Auer deferences, in dismissing the case, as well as to reconsider the preliminary injunction on Grimm's use of the boys' restroom.

[20] Shortly upon taking office in January 2017, President Donald Trump took steps to reject past guidance set by the Obama administration related to transgender rights.

Judge Arenda Wright Allen of the United States District Court for the Eastern District of Virginia denied the Gloucester County School Board's motion to dismiss the case in May 2018, and ruled that Grimm had a valid claim of discrimination under Title IX of the Education Amendments of 1972, as well as the U.S. Constitution's equal protection clause.

The majority opinion was guided heavily by the Supreme Court decision Bostock v. Clayton County which had determined that in Title VII of the Civil Rights Act of 1964 for employment discrimination, "on the basis of sex" includes protection for sexual orientation and gender identity.

[24][31] The Supreme Court denied certiorari on June 28, 2021, with Justices Clarence Thomas and Samuel Alito dissenting, leaving the decision of the Fourth Circuit intact.