Sitkoff's scholarly work focuses on trusts and estates, a field of law with relatively few prominent scholars. He is co-author of "Wills, Trusts, and Estates", the leading trusts and estates casebook in the United States; has published in leading academic journals such as the Yale Law Journal, Columbia Law Review, and the Journal of Law and Economics; has appeared as a commentator on CNN; and has had his work on the effects of the abolition of the rule against perpetuities featured in the Wall Street Journal.