After graduating from Yale Law School, Professor Cole served as a law clerk to Judge Arlin M. Adams of the United States Court of Appeals for the Third Circuit. Professor Cole then became a staff attorney for the Center for Constitutional Rights where he litigated a number of major First Amendment cases, including Texas v. Johnson, 491 U.S. 397 (1989), United States v. Eichman, 496 U.S. 928 (1990), which established that the First Amendment protects flag burning, and National Endowment for the Arts v. Finley, which challenged the constitutionality of content restrictions on federal art funding. He continues to litigate First Amendment and other constitutional issues as a volunteer staff attorney at the Center.
He has published in a variety of areas, including civil rights, criminal justice, constitutional law and law and literature. He is the legal affairs correspondent for The Nation, a columnist for Legal Times, a commentator on National Public Radio; All Things Considered, and the author of No Equal Justice: Race and Class in the American Criminal Justice System (New Press, 1999), which was named Best Nonfiction Book of 1999 by the Boston Book Review and best book on an issue of national policy in 1999 by the American Political Science Association.