Caroline Rule

Caroline Rule is a vigorous and determined advocate for her clients, many of whom face white collar criminal investigations and/or prosecutions, or civil tax audits and investigations. She represents clients facing criminal charges of alleged tax fraud and tax evasion, failure to file tax returns, bank fraud, health care fraud, money-laundering, and other white collar crimes. Ms. Rule regularly defends individuals and corporations under investigation by a variety of governmental and regulatory agencies and prosecutors’ offices around the country, including:

  • the United States Attorneys’ Offices for the Southern and Eastern Districts of New York and New Jersey
  • New York District Attorneys’ Offices
  • the Tax Division of the United States Department of Justice, and
  • the Criminal Investigation function of the Internal Revenue Service. 

Ms. Rule also successfully represents clients in civil tax matters, including sensitive audits by the IRS and state tax authorities, civil “tax shelter” matters, matters involving failure to report offshore assets, matters where clients seek abatement of penalties, and residency issues.  In addition, Ms. Rule represents clients in investigations by the New York City Business Integrity Commission. Ms. Rule’s aim is first and foremost to help her clients, whether individuals or corporations, to defeat allegations of fraud in order to preserve their reputations and, in the case of individuals, their careers. 

Ms. Rule works to improve the clarity and application of laws through her chairmanship of the Subcommittee on Tax Crimes, Criminal Litigation Committee, ABA Litigation Section, as well as her active memberships in the New York Council of Defense Lawyers; Criminal Advocacy Committee, New York City Bar Association; Administrative Practice Committee, ABA Tax Section; Federal Bar Council Committee on Sentencing Reform and Alternatives to Incarceration; and Bloomberg BNA U.S. Income Tax Advisory Board.  She is also a Master of the Federal Bar Council Inn of Court.

Caroline Rule Representative Matters

  • Persuaded the United States Attorney's Office for the District of New Jersey to charge a doctor with one count of making a false statement to the IRS, when he had in fact evaded $4.2 million in taxes over a period of years; and then persuaded the Court to sentence the doctor to probation and community service, when the advisory sentence under the United States Sentencing Guidelines was 36 months in jail.

  • Represented the former head of KPMG’s tax practice in what was then termed the largest tax fraud prosecution in United States history, and obtained dismissal of the entire indictment on grounds of prosecutorial misconduct.
  • Persuaded the Criminal Investigation function of the IRS that a client who failed to collect and pay over employment taxes for many years did not act willfully, and that the matter should be transferred back to the IRS Civil Division.

  • In connection with a very large and complicated estate, persuaded the IRS that, by placing stock certificates with bearer stock powers into a safety deposit box to which the executor had access, the decedent had made a completed gift to the executor, which saved the estate millions in estate taxes.
  • Negotiated a misdemeanor plea and non-jail sentence for the owner of a medical laboratory who characterized kick-backs to doctors as ordinary business expenses.

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Caroline Rule has been recognized by "New York Super Lawyers" since 2011.

Before Joining Kostelanetz & Fink

  • Associate at Rabinowitz, Boudin, Standard, Krinsky & Lieberman, PC
  • Served as court-appointed counsel for indigent criminal defendants at the Office of the Appellate Defender for a two-year term.
  • Associate at Cahill Gordon & Reindel, LLP
  • Law Clerk to the Honorable John J. Gibbons, Chief Judge, United States Court of Appeals for the Third Circuit



Tel: 212.808.8100


September 26, 2017

Caroline Rule participated in a panel titled “How You Can And Cannot Use Information That You Learn When Preparing Returns, Including In Advertising Your Service Plus Other Ethical Issues” at the Zicklin Executive Taxation Series

December 02, 2016

How Not to Waive Privilege When Consulting Non-Attorney Experts or Professionals

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December 02, 2016

How Not to Waive Privilege When Consulting Non-Attorney Experts or Professionals

October 16, 2016

Applying Civil Penalties for Willful Violations of FBAR Requirements

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University of Cape Town, South Africa, B.F.A. (1981), With Honors

San Francisco Art Institute, M.F.A. (1984), Cum Laude

Yale Law School, J.D. (1989), Senior Editor, Yale Law Review

Bar Admissions

New York State, 1990

U.S.D.C., S.D.N.Y., 1990

U.S.D.C., E.D.N.Y., 1998

U.S. Tax Court, 1998

U.S. Court of Appeals (2d Cir.), 2007

U.S. Court of Appeals (3d Cir.), 1990