Holmes is senior counsel with the Chicago law firm of Freeborn & Peters, where he practices in the areas of trade regulation and general business representation. He has also been an adjunct professor at the Loyola University of Chicago School of Law. He is an honors graduate of Harvard Law School and Stanford University and is a member of the Illinois, California, and Chicago Bar Associations. Holmes is a frequent speaker at conferences before professional, industry, and government groups and is the author of numerous books and articles.