Benjamin Z. Eisenstat is a Member in Caplin & Drysdale’s Washington, D.C. office, where he assists individuals and corporations in all manner of civil and criminal tax controversies. Over the past decade, Mr. Eisenstat has helped clients effectively return to tax compliance and move forward with their lives, whether that involves correcting tax issues prior to contact from the government, navigating IRS audits, or defending against criminal investigations.

Mr. Eisenstat has consistently achieved favorable results for his clients. In the criminal context, he has a strong record of persuading the government not to bring forth an indictment.  And when cases have reached the plea and sentencing stage, Mr. Eisenstat has successfully advocated for substantial downward departures and variances from the sentencing guidelines, including a recent case where a client received a non-incarceratory sentence despite a guidelines range of 24 to 30 months in prison. In the civil context, he consistently helps his clients minimize their tax and penalty exposure.  To that end, Mr. Eisenstat recently assisted a captive insurance participant in achieving a full concession from the IRS in a docketed case in the U.S. Tax Court.

Mr. Eisenstat is also active with the American Bar Association’s Section of Taxation. He is currently a Co-Chair of the Civil and Criminal Tax Penalties – Criminal Litigation Sub-Committee.


Mr. Eisenstat has experience representing clients in a broad range of cases including:

  • All stages of criminal tax investigations conducted by the U.S. Justice Department and IRS Criminal Investigation from the pre-indictment phase, to the decision whether to plea or go to trial, to sentencing.  
  • Advising on highly-sensitive civil tax examinations of individuals or companies where potential fraud issues may arise (so-called “eggshell audits”).
  • Representing clients before IRS appeals and the US Tax Court.
  • Assisting clients in all stages of IRS examinations involving captive insurance arrangements, a current enforcement priority for the IRS.
  • Assisting clients in criminal investigations or civil tax examinations specifically arising from unreported foreign accounts, assets or structures.
  • Assisting clients in all manner of IRS collections matters, including negotiations of installment agreements and offers-in-compromise.
  • Representing clients in connection with recently enacted qui tam provisions enabling private persons to bring claims for potential violations of District of Columbia and New York tax requirements, including cases that arise from allegations relating to a taxpayer’s state of domicile or residence.
  • Assisting individuals and corporations in coming back into tax compliance prior to contact from the IRS.

Admissions & Education

Bar & Court Admissions
  • District of Columbia
  • New York
  • U.S. District Court, District of Columbia
  • U.S. Tax Court

LL.M., Taxation, Georgetown University Law Center, 2015

J.D., Georgetown University Law Center, 2014

B.A., University of Pennsylvania, 2010

Recognitions & Noteworthy

Honors & Recognitions
  • The Legal 500, Recommended, 2024
  • Best Lawyers: Ones to Watch­, 2024

Professional Activities & Affiliations

Professional Activities

Member and Co-Chair of the Civil and Criminal Tax Penalties – Criminal Litigation Sub-Committee, Section of Taxation, American Bar Association

Member, The Tax Lawyer (during law school)

Newsroom & Publications

Speaking Engagements
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