[1] Following graduation from law school, Wynn served for four years on active duty in the Judge Advocate General's Corps, U.S. Navy.
[1] On August 5, 1999, President Bill Clinton nominated Wynn to serve on the United States Court of Appeals for the Fourth Circuit to fill a vacancy created by Judge James Dickson Phillips Jr.'s decision to assumed senior status in 1994.
[1] On November 4, 2009, President Barack Obama nominated Wynn and Special Superior Court Judge for Complex Business Cases Albert Diaz for seats on the Fourth Circuit.
[1][9] Obama's renomination of Wynn and nomination of Diaz were jointly endorsed by North Carolina senators Kay Hagan, a Democrat, and Richard Burr, a Republican.
On December 13, 2024, Wynn rescinded his senior status announcement, opting to remain an active judge on the Fourth Circuit and therefore depriving Trump the opportunity to nominate his replacement.
Senate Minority Leader Mitch McConnell, suggested that Wynn would face ethics complaints and requests for recusals in cases involving the incoming Trump administration.
[24] In 2014, Wynn wrote the majority opinion preliminarily enjoining portions of a North Carolina law that denied minority groups equal access to voting.
The majority held that the North Carolina General Assembly's "new provisions target[ed] African Americans with almost surgical precision."
Wynn wrote the section of the majority opinion as to remedy, permanently enjoining the State from implementing the unconstitutional provisions.
[30] In a 10–6 decision, joined by Judge Wynn, the full court held that a public charter school was a state actor for the purposes of 42 U.S.C.
Senior Judge Barbara Milano Keenan, writing for the majority, also concluded that the school’s dress code, which "requires female students to wear skirts to school based on the view that girls are 'fragile vessels' deserving of 'gentle' treatment by boys," plainly violates the Fourteenth Amendment's Equal Protection Clause.
During his tenure on the Supreme Court of North Carolina, Wynn authored an opinion abolishing the longstanding invitee/licensee framework for evaluating premises-liability claims and replacing it with a new standard under which property owners owe a duty of reasonable care to all lawful visitors.
In a 2–1 decision, the court held that a Virginia school board violated Title IX when it prevented a transgender man from using the boys' bathroom.
No less than the recent historical practice of segregating Black and white restrooms, schools, and other public accommodations, the unequal treatment enabled by the Board's policy produces a vicious and ineradicable stigma.
[37][38] In a concurring opinion, Wynn became the first federal appellate judge to conclude that Article I, Section 5 does not render states "powerless to regulate candidates or ballot access" for congressional office.
A contrary holding, he wrote, would not only do violence to the Constitution's text but would also mean states would be unable to prevent "'fraudulent or unqualified candidates such as minors, out-of-state residents, or foreign nationals' from running for office."
Wynn authored one of the first opinions applying the plausibility pleading standard set forth in Bell Atlantic Corp. v. Twombly, 550 U.S. 544 (2007), to an attempted monopolization case under Section 2 of the Sherman Antitrust Act.
The opinion discusses at length what types of facts a complaint must allege to sufficiently plead a relevant geographic market.
"[39] Wynn's 2020 lecture explained his definition of judicial activism, exemplified by the Supreme Court's decision in Rucho v. Common Cause.
He proposed that a court engages in judicial activism if it fails to consider well-established decisional tools that are relevant to deciding a particular case.