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Caroline Rule

Caroline Rule

Caroline Rule

Partner


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New York City
T: 212.808.8100
F: 212.808.8108

Caroline Rule is a vigorous and determined advocate for her clients, many of whom face white collar criminal investigations/prosecutions or civil tax audits and investigations. Over the course of her 28-year career, Ms. Rule has successfully helped individual and corporate clients defeat allegations of fraud in order to preserve their reputations and, in the case of individuals, their careers.

Ms. Rule’s winning record includes cases involving alleged tax fraud, tax evasion, failure to file tax returns and related forms, bank fraud, healthcare fraud, money laundering, and other white collar controversies. Ms. Rule has achieved outstanding results for individuals and corporations under investigation by governmental and regulatory agencies, and prosecutors’ offices in New York and around the country.

Ms. Rule also successfully represents clients in complex civil tax matters, including sensitive audits by the IRS and state tax authorities, as well as cases involving civil “tax shelters,” failure to report offshore assets, abatement of penalties, and residency issues.  In addition, Ms. Rule represents clients in investigations by the New York City Business Integrity Commission.

Ms. Rule has published numerous articles in legal journals and magazines, and is author of the BNA Tax Management Portfolio No. 623 – 3rd “IRS Procedures: Examinations and Appeals.”

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. She also is an active member of the New York Council of Defense Lawyers; the Criminal Advocacy Committee and the Mass Incarceration Task Force of the New York City Bar Association; the Administrative Practice Committee, ABA Tax Section; and the Federal Bar Council Committee on Sentencing Reform and Alternatives to Incarceration.  She is also a Master of the Federal Bar Council Inn of Court.

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 Journal

New Jersey, 1989

New York, 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

U.S. Court of Appeals (9th Cir.), 2019

U.S. Supreme Court, 2014

  • 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.
  • 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.
  • Quashed a prosecution for tax evasion by demonstrating that the government’s calculations of the client’s gambling earnings were based on faulty mathematics.
  • Averted the prosecution of an NBA referee who failed to declare as income the differential between the value of first class air tickets provided by the NBA (which he cashed in) and the value of economy class tickets, despite the fact that other referees were prosecuted for the same conduct.
  • Quashed the criminal prosecution of business owners who regularly, over a period of years, structured bank deposits and withdrawals to avoid banks filing currency transaction reports.
  • Obtained non-jail sentences for many clients when the United States Sentencing Guidelines called for substantial periods of incarceration.
  • Avoided numerous criminal prosecutions and crippling monetary penalties by assisting clients in making voluntary disclosures of foreign bank accounts and undeclared income earned by those accounts.
  • Persuaded the IRS that an elderly client with memory loss should not pay any penalty at all in connection with a voluntary disclosure of a foreign bank account.
  • Successfully argued that the IRS should not seek to prosecute two separate clients who failed for years to declare foreign bank accounts, records of which the government obtained from third parties, after both clients lied to IRS agents about their ownership of the accounts.
Caroline Rule Super Lawyer Badge

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

  • 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