Simon joined the Immigrant Advocacy Program in 2011, and became its Legal Director in 2015. He specializes in federal civil rights litigation on behalf of immigrants, and has led cases of nationwide impact challenging immigration detention of adults and children. Simon co-directs the Immigration Litigation Clinic at the George Mason University School of Law. In 2017, Simon was named an “Up & Coming Lawyer” by Virginia Lawyers Weekly, and won the Wynn Newman Equality Award from Americans for Democratic Action. He was awarded the 2016 Legal Aid Lawyer of the Year award from the Virginia State Bar, the 2013 LASSY award from the Virginia Poverty Law Center for greatest achievement in consumer law, and was a Wasserstein Public Interest Fellow at Harvard Law School in November 2021. Simon is a graduate of Columbia University and Yale Law School, where he was awarded the C. LaRue Munson prize for excellence in clinical practice.