Jerome R. Hellerstein was a professor of law at New York University School of Law who specialized in taxation studies. He also practiced tax law for many years and included among his many accomplishments authorship of a book he hoped would inform the general public about the major federal income tax problems that existed as of 1963, the publication date of Taxes, Loopholes and Morals.

Professor Hellerstein was acutely concerned about the federal tax gap of his day. His book refers frequently to tax reform proposals initiated by President John F. Kennedy and also mentions some of the tax issues that confronted President Franklin D. Roosevelt during the early years of Hellerstein's career as a tax professional. Taxes, Loopholes and Morals explores the problems of setting different rates of taxation for capital gains versus ordinary income, allowing entity forms to dictate tax results, and inadequate policing of income underreporting; as well as compliance failures involving a variety of federal tax features including business deductions, assignments of income via gifts, foreign tax allowances, and charitable contribution deductions.

Ultimately, Professor Hellerstein's concerns about the integrity of the federal income tax system fell into three categories: Fundamental structural disparities of the Internal Revenue Code that clearly favor some taxpayers over others; tax sheltering devices derived ingeniously from otherwise neutral statutory provisions; and outright cheating and dishonesty resulting from a breakdown in the efficacy of social mores and personal morals. This paper discusses each of these concerns, first as Hellerstein saw them and then in our modern context, with a view toward future progress to reduce the federal income tax gap that now has deep historical roots.